694
Views
15
CrossRef citations to date
0
Altmetric
Review Article

S-Carboxymethyl-L-cysteine

&
Pages 129-147 | Received 07 Jul 2011, Accepted 07 Oct 2011, Published online: 12 Apr 2012

References

  • Adachi, A., Sarayama, Y., Shimizu, H., Yamada, Y., Horikawa, T. (2005). Thiodiglycolic acid as a possible causative agent of fixed drug eruption provoked only after continuous administration of S-carboxymethyl-L-cysteine: case report and review of reported cases. Brit J Dermatol 153:226–228.
  • Agnus, D. E., Ser, J.-C. (2000). Composition for the treatment of the nails, containing a sulphur-bearing amino acid. U.S. Patent 6,123,930 to L’Oréal, Paris, France (September 26, 2000).
  • Aiache, J. M., Borel, J. P., Kantelip, J. P. (1982) Comparative bioavailability of S-carboxymethyl-L-cysteine from two dosage forms: hard gelatin capsule and syrup. Biopharm Drug Dispos 9:275–281.
  • Alt, N., Carson, J. A., Alderson, N. L., Wang, Y., Nagai, R., Henle, T., et al. (2004). Chemical modification of muscle protein in diabetes. Arch Biochem Biophys 425:200–206.
  • Arias, I. M., Furman, M., Tapley, D. F., Ross, J. E. (1963). Glucuronide formation and transport of various compounds by Gunn rat intestine in vivo. Nature 197:1109–1110.
  • Armstrong, M. D., Lewis, J. D. (1951). Growth experiments with thioether derivatives of cysteine and homocysteine. J Biol Chem 189:461–466.
  • Ayesh, R., Mitchell, S. C., Waring, R. H., Smith, R. L. (1988). Taste sensitivity to phenylthiourea: lack of correlation with the debrisoquine and carboxymethylcysteine oxidation polymorphisms. Br J Clin Pharmacol 25:664P.
  • Aylward, M. (1973). A between-patient double-blind comparison of S-carboxymethylcysteine and bromhexine in chronic obstructive bronchitis. Curr Med Res Opin 1:219–227.
  • Bacq, Z. M. (1975). Protection by thiols against poisoning by radiomimetic agents. In: Bacz, Z. M. (Ed.), Sulfur-containing radioprotective agents. International encyclopedia of pharmacology and therapeutics (pp. 303–318). Oxford, UK: Pergamon.
  • Barnsley, E. A. (1964). The metabolism of S-methyl-L-cysteine in the rat. Biochim Biophys Acta 90:24–36.
  • Barnsley, E. A., Eskin, N. A. M., James, S. P., Waring, R. H. (1969). The acetylation of S-alkylcysteines by the rat. Biochem Pharmacol 18:2393–2401.
  • Baudrimont, A., Malguti, A. (1837). Recherches sur la cysteine. C R Hebd Séanc Acad Sci 5:394–399.
  • Baumann, E. (1884). Über Cystin und Cystein. Hoppe-Seyler’s Z Physiol Chem 8:299–305.
  • Bélanger, P. M. (1997). Focus on chronopharmacology. Drug Metab Pharm News 4:22–26.
  • Beneke, P. C., Müller, F. O. (1983). S-Carboxymethylcysteine: Inhibition of gastric emptying in rats. IRCS Med Sci 11:478–479.
  • Beneke, P. C., Müller, F. O., Middlecote, B. D. (1983). S-Carboxymethylcysteine: protection against paracetamol-induced hepatotoxicity in mice. IRCS Med Sci 11:476–477.
  • Berk. (1973). Monograph on S-carboxymethyl-L-cysteine (pp. 1–81). Guildford, Surrey, UK: Berk Pharmaceutical Limited.
  • Berzelius, J. J. (1831). Lehrbuch der Chemie (translated from the Swedish by Wöhler F) (part 1, vol. 4, pp. 404–405). Dresden: Arnoldischen Buchhandlung; Berlin: Schade AW.
  • Berzelius, J. J. (1832). Thierchemie; Harnsteine. Jahresber Fortschr Phys Wiss 11:337–338.
  • Berzelius, J. J. (1833). Traité de Chimie (translated by Esslinger M) (part 2, vol. 7, p. 424). Paris: Firmin Didot Freres.
  • Bi, H, Zhong, G, Huang, M, Zhou, S, Huang, L, Zeng, G, et al. (2005). Bioequivalence evaluation of two tablet formulations of carbocysteine in healthy Chinese men. J Appl Res 5:598–604.
  • Binkley, F. (1950). Enzymatic cleavage of thioethers. J Biol Chem 182:287–296.
  • Binkley, F., Okeson, D. (1950). Purification of the enzyme responsible for the cleavage of cystathionine. J Biol Chem 182:273–278.
  • Bird, G. (1842). Observations on urinary concretions and deposits: with an account of the collection in the museum of Guy’s Hospital. Guys Hosp Rep 7:175–232.
  • Block, E. (1992). The organosulfur chemistry of the genus Allium—implications for the organic chemistry of sulphur. Angew Chem Int Ed Engl 31:1135–1178.
  • Blood, F. R., Lewis, H. B. (1941). The metabolism of sulfur. XXIX. S-Carboxymethylcysteine. J Biol Chem 139:407–412.
  • BNF. (2007). British National Formulary, 53rd ed. (p. 173). London: BMJ/RPS.
  • Bodmer, J., Waring, R. H. (1981). Tissue distribution of S-carboxymethylcysteine in the rat: concentration in mucus-producing organs including the prostate. Biochem Soc Trans 9:549–550.
  • Boonyapiwat, B., Panagopoulos, P., Jones, H., Mitchell, S. C., Forbes, B., Steventon, G. B. (2005). Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine in HepG2 cells. Drug Metab Drug Interact 21:1–18.
  • Boonyapiwat, B., Forbes, B., Mitchell, S. C., Steventon, G. B. (2008). Phenylalanine 4-monoxygenase and the S-oxidation of S-carboxymethyl-L-cysteine by human cytosolic fractions. Drug Metab Drug Interact 23:261–282.
  • Boonyapiwat, B., Panaretou, B., Forbes, B., Mitchell, S. C., Steventon, G. B. (2009). Human phenylalanine monooxygenase and thioether metabolism. J Pharm Pharmacol 61:63–67.
  • Boonyapiwat, B., Mitchell, S. C., Steventon, G. B. (2011). Recombinant heteromeric phenylalanine monooxygenase and the oxygenation of carbon and sulfur substrates. J Pharm Pharmacol 63:558–564.
  • Bouillon, C., Abegg, J.-L., Koulbanis, C., Darmenton, P. (1983). Process for reinforcing fragile or brittle nails and a composition containing cationic polymer for use in said process. U.S. Patent 4,381,294 to L’Oréal, Paris, France (April 26, 1983).
  • Braga, P. C., Borsa, M., De Angelis, L., Bossi, R., Allegra, L., Scaglione, F., et al. (1982). Pharmacokinetic behavior of S-carboxymethylcysteine-Lys in patients with chronic bronchitis. Clin Ther 4:480–488.
  • Brakenhoff, J. P. G., Commandeur, J. N. M., Lamoree, M. H., Dubelaar, A. C., Van Baar, B. L. M., Lucas, C., et al. (1993). Identification and quantitative determination of glutathione-related urinary metabolites of fotemustine, a new anticancer agent. Xenobiotica 23:935–947.
  • Brand, E., Block, R. J., Kassell, B., Cahill, G. F. (1936). Carboxymethylcysteine metabolism, its implication on therapy in cystinuria and on methionine-cysteine relationship. Proc Soc Exp Biol Med 35:501–506.
  • Brandolini, L., Allegretti, M., Berdini, V., Cervellera, M. N., Mascagni, P., Rinaldi, M., et al. (2003). Carbocysteine lysine salt monohydrate (SCMC-LYS) is a selective scavenger of reactive oxygen intermediates (ROIs). Eur Cytokine Netw 14:20–26.
  • Brockmoller, J., Simane, Z. J., Roots, J. (1988). HPLC-Analysis of S-carboxymethylcysteine and its sulphoxide metabolites. Drug Metab Drug Interact 6:447–456.
  • Brockmoller, J., Staffeldt, B., Roots, I. (1991). Evaluation of the proposed sulphoxidation pathway of carbocysteine in man by HPLC quantification. Eur J Clin Pharm 40:387–392.
  • Bron, J. (1988). Relative bioavailability of carbocysteine from three dosage forms investigated in healthy volunteers. Biopharmaceut Drug Dispos 9:97–111.
  • Brow, D. T. (1988). Carbocysteine. Drug Intell Clin Pharm 22:603–608.
  • Brumass, V., Venturini, M., Filella, M., Berthon, G. (1989). Quantitative investigation of copper (II) and zinc (II) complexes with S-carboxymethyl-L-cysteine and computer-simulated appraisal of their potential significance in vivo. J Inorg Biochem 37:309–323.
  • Buziassy, C., Mazelis, M. (1964). The formation of S-carboxymethyl-L-cysteine by radish (Raphanus sativus) seedling homogenates. Biochim Biophys Acta 86:185–186.
  • Cakan, G., Turkoz, M., Turan, T., Ahmed, K., Nagatake, T. (2003). S-Carboxymethylcysteine inhibits the attachment of Streptococcus pneumoniae to human pharangeal epithelial cells. Microb Pathog 34:261–265.
  • Centro Toxicológico Regional. (2008). Elba Luz Bermúdez. Estadisticas 1982–2008. Barquisimento, Lara, Venezuela: Hospital Universitario de Pediatria Dr Agustin Zubillaga.
  • Chakrabortty, M., Mohanty, S. R. (1979). Solvent extraction of zirconium from hydrochloric acid solutions by sulfoxides and their mixtures. J Radioanalyt Chem 53:131–143.
  • Chapoton, C., Millet, J. M. (1986). Hair preparations incorporated into brushes and combs. French Patent (Fr. Demande) FR 2,580,478 (October 24, 1986).
  • Chen, T.-C., Hong, A. (1995). Chelating extraction of lead and copper from an authentic contaminated soil using N-(2-acetamido)iminodiacetic acid and S-carboxymethyl-L-cysteine. J Hazard Mater 41:147–160.
  • Corcuff, P., Berrebi, C. (1981). Composition containing stigmasterol for hair treatment. French Patent (Fr. Demande) FR 2,484,831 to L’Oréal, Paris, France (December 24, 1981).
  • Cornillot, P. (1961). Combinations of glucuronic acid in urine. C R Séanc Soc Biol 252:2465–2467.
  • Cotton, F. A., Francis, R. (1960). Sulfoxides as ligands. 1. Preliminary survey of methyl sulfoxide complexes. J Amer Chem Soc 82:2986–2991.
  • Deichmann, W. B., Mergard, E. G. (1948). Comparative evaluation of methods employed to express the degree of toxicity of a compound. J Ind Hyg Toxicol 30:373–378.
  • De Marco, C., Rinaldi, A., Piccaluga, G., Fadda, M. B. (1974). Identification of S-carboxymethyl-thiopyruvate as the product of oxidative deamination of S-carboxymethyl-cysteine. Mol Cell Biochem 3:3–7.
  • De Marco, C., Rinaldi, A., Dessi, M. R., Dernini, S. (1976). Oxidation of S-carboxymethyl-selenocysteine by L-aminoacod oxidase and D-aspartate oxidase. Mol Cell Biochem 12:89–92.
  • Dersch, F., De Angelus, M. R. (1960). Compounds for reducing fog in photographic emulsions. U.S. Patent 2,955,036 to General Aniline and Film Corp. (October 4, 1960).
  • De Schutter, J. A., Van der Weken, G., Van der Bossche, W., De Moerloose, P. (1988). Determination of S-carboxymethyl-L-cysteine in serum by reversed-phase ion-pair liquid chromatography with column switching following pre-column derivatization with σ-phthalaldehyde. J Chromatogr Biomed Appl 428:301–310.
  • Dickens, F. (1933a). Iodoacetic acid, glutathione, and tissue glyoxalase. Nature 131:130–131
  • Dickens, F. (1933b). CLII. Interaction of halogenacetates and SH compounds. The reaction of halogenoacetic acids with glutathione and cysteine. The mechanism of iodoacetate poisoning of glyoxalase. Biochem J 27:1141–1151.
  • Dolfini, E., Testa, R. (1979). Gas liquid chromatographic determination of S-carboxymethylcysteine in human urine. Il Farmaco 34:114–120.
  • Draize, J. H., Freeman, M. V., Smith, P. K. (1956a). Some aspects of the mechanism of toxicity of thioglycolate. J Pharmacol Expt Ther 118:296–303.
  • Draize, J. H., Freeman, M. V., Smith, P. K. (1956b). Some aspects of the absorption, distribution, and excretion of sodium thioglycolate. J Pharmacol Expt Ther 118:304–308.
  • Draminski, W., Trojanowska, B. (1981). Chromatographic determination of thiodiglycolic acid—a metabolite of vinyl chloride. Arch Toxicol 48:289–292.
  • Dubief, C., Mellul, M., Loussouarn, G., Saint-Léger, D. (2005). Hair care products. In: Bouillon, C., Wilkinson, J. D. (Eds.), The science of hair care, 2nd ed. (p. 134). Boca Raton, Florida, USA: CRC.
  • Dubruc, C., Hermann, P. H., Haddouche, A., Badarani, M. M., Thenot, J. P. (1987). Determination of S-carboxymethyl-L-cysteine in plasma by high performance liquid chromatography with column switching following precolumn derivatization. J Chromatogr Biomed Appl 417:208–215.
  • Dufetel, D., Estradier, F., Gaetani, Q., Hocquaux, M. (1998). Process for retarding hair loss and for inducing and stimulating its growth. U.S. Patent 5,760,043 to L’Oréal, Paris, France (June 2, 1998).
  • du Vigneaud, V., Loring, H. S., Craft, H. A. (1934). The oxidation of the sulfur of homocysteine, methionine, and S-methylcysteine in the animal body. J Biol Chem 105:481–488
  • Egi, N. (1963a). Glucuronic acid conjugates of amino acids in urine. I. Glucuronic acid conjugates of glycine, aspartic, and glutamic acids in normal human urine. Hiroshima J Med Sci 12:137–142.
  • Egi, N. (1963b). Glucuronic acid conjugates of amino acids in urine. II. Glucuronic acid conjugates of amino acids in the urine of patients and animals. Hiroshima J Med Sci 12:143–149.
  • Esaki, N., Tanaka, H., Yamamoto, T., Soda, K. (1981). Further characterization of L-methionine γ-lyase and enzymatic synthesis of sulphur amino acids. Bull Inst Chem Res Kyoto Univ 59:321–331.
  • Fennell, T. R., Kedderis, G. L., Sumner, S. C. (1991). Urinary metabolites of [1,2,3-13C]-acrylonitrile in rats and mice by 13C nuclear magnetic resonance spectroscopy. Chem Res Toxicol 4:678–687.
  • Fiori, A., Costa, M., Barboni, E. (1972). Oxidation of S-carboxymethyl-L-cysteine by glutamate dehydrogenase. Physiol Chem Phys 4:457–466.
  • Forestier, S., Lagrange, A., Lang, G., Shroot, B. (1991). Medicinal and cosmetic compositions. U.S. Patent 5,055,452 to L’Oréal, Paris, France (August 10, 1991).
  • Friedmann, E. (1902a). Ueber die Konstitution des Eiweisscystins. Beitr Chem Physiol Pathol 2:433–434.
  • Friedman, E. (1902b). Der Kreislauf des Schwefels in der organischen Natur. A. Ueber die Bindung des Schwefels in Eiweiss. Ergebn Physiol 1:15–31.
  • Friedmann, E. (1903). Beziehungen der schwefelhaltingen Eiweissabkömmlinge. 1. Ueber die Konstitution des Cystins. Beitr Chem Physiol Pathol 3:1–46.
  • Gaetani, E., Laureri, C. F., Vitto, M., Bordi, F. (1982). Determination of S-carboxymethylcysteine in plasma by HPLC and fluorimetric detection. Il Farmaco 37:235–238.
  • Ghillione de Torviso, S. (1971). Clinical trial of a new mucolytic, S-carboxymethylcysteine. Arch Argent Pediatr 69:247–248.
  • Glass, S. D. (1855). A practical treatise on the diseases, injuries, and malformations of the urinary bladder, the prostate, and the urethra, 2nd ed. (p. 455). Philadelphia, Pennsylvania, USA: Blanchard and Lea.
  • Gmelin, L. (1852). Handbuch der Chemie, 4th ed. (p. 133). Heidelberg, Germany: Winter.
  • Godeneche, D., Labarre, P., Moreau, M. F., Madelmont, J. C., Rapp, M., Papon, J., et al. (1993). Main urinary metabolites of two cysteamine-containing 2-(chloroethyl) nitrosoureas in rats. Drug Metab Dispos 21:93–99.
  • Goodman, L., Ross, L. O., Baker, B. R. (1958). Potential anticancer agents. V. Some sulfur-substituted derivatives of cysteine. J Org Chem 23:1251–1257.
  • Goreish, A. H., Bednar, S., Jones, H., Mitchell, S. C., Steventon, G. B. (2004). Phenylalanine 4-monoxygenase and the S-oxidation of S-carboxymethyl-L-cysteine. Drug Metab Drug Interact 20:159–174.
  • Grasse, F. R., James, S. P. (1972). Biosynthesis of sulphated hydroxypentylmercaturic acids and the metabolism of 1-bromopropane in the rat. Xenobiotica 2:117–127.
  • Green, T., Hathaway, D. E. (1977). The chemistry and biogenesis of the S-containing metabolites of vinyl chloride in rats. Chem Biol Interact 17:137–150.
  • Gregory, W. L., James, O. F. W., Turner, I., Meese, C. O., Idle, J. R. (1993). Re-evaluation of the metabolism of carbocisteine in a British white population. Pharmacogenetics 3:270–274.
  • Haley, C. S., Waring, R. H., Mitchell, S. C., Shah, R. R., Idle, J. R., Smith, R. L. (1985). Lack of congruence of S-carboxymethyl-L-cysteine sulphoxidation and debrisoquine 4-hydroxylation in a Caucasian population. Xenobiotica 15:445–450.
  • Hanafi, T., Xinfan, H. (2007). Cosmetic and cosmeceutical compositions for restoration of skin barrier function. U.S. Patent 7,300,649 to GenePharm Inc., Sunnyvale, California, USA (November 27, 2007).
  • Hannestad, U., Sorbo, B. (1979). Determination of 3-mercaptolactate, mercaptoacetate and N-acetylcysteine in urine by gas chromatography. Clin Chim Acta 95:189–200.
  • Harada, S., Shimizu, H. (2003). A case of fixed drug eruption due to continuous intake of carbocysteine. Jpn J Dermatoallergol 11:57–61.
  • Havez, R., Degand, P., Roussel, P., Randoux, A. (1970). Mode d’action biochemique des derivés del la cysteine sur le mucus bronchique. Poumon Coeur 26:81–90.
  • Hefner, R. E., Jr., Watanabe, P. G., Gehring, P. J. (1975). Preliminary studies on the fate of inhaled vinyl chloride monomer (VCM) in rats. Environ Health Perspect 11:85–95.
  • Henry, W. (1831). The elements of experimental chemistry, 11th ed. (vol. 2, pp. 384–397). Philadelphia, Pennsylvania, USA: Robert Desilver.
  • Hess, W. C., Sullivan, M. X. (1943). Canine cystinuria. Urinary excretion of cystine following the administration of homocystine, homocysteine, and some derivatives of cystine and cysteine. J Biol Chem 149:543–548.
  • Hill, R. M., Lewis, H. B. (1924). VII. The oxidation of some sulfur compounds related to cystine in the animal organism. J Biol Chem 59:557–567 (also quoting unpublished work by L.E. Root).
  • Hofmann, U., Eichelbaum, M., Seefried, S., Meese, C. O. (1991). Identification of thiodiglycolic acid, thiodiglycolic acid sulfoxide, and (3-carboxymethylthio)lactic acid as major human biotransformation products of S-carboxymethyl-L-cysteine. Drug Metab Dispos 19:222–226.
  • Hong, A. P., Chen, T.-C., Okey, R. W. (1993). Extraction of copper and zinc from soils with chelates. Water Environment Federation, 66th Annual Conference and Exposition, October 3–7, 1993, Anaheim, California, USA. AC93-043-001. 5:171–182.
  • Hong, A. C., Chen, T.-C., Okey, R. W. (1995). Chelating extraction of copper from soil using S-carboxymethylcysteine. Water Environ Res 67:971–978.
  • Hong, P., Li, C., Jiang, W., Chen, T. C., Peters, R. (2002). Chelating agents for extraction of heavy metals from the soil: complexing power, selectivity, and recoverability. In: Tedder, D. W., Pohland, F. G. (Eds.), Emerging technologies in hazardous waste management 8 (pp. 9–20). New York: Kluwer Academic.
  • Hong, A. P. K., Jiang, W. (2005). Factors in the selection of chelating agents for extraction of lead from contaminated soil: effectiveness, selectivity, and recoverability. In: Nowack, B., VanBriesen, J. M. (Eds.), Biogeochemistry of chelating agents (pp. 421–432). ACS Symposium Series 910. Washington, DC: Oxford University Press for the American Chemical Society.
  • Hooper, C., Calvert, J. (2008). The role of S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis 3:659–669.
  • Huyen, V. N., Garcet, S., Lakah, L. (1966). Hypersecretion experimentale du mucus bronchique chez le rat. II. Application a l’étude d’un agent dit mucolytique, la S-carboxymethylcysteine. C R Séanc Soc Biol 160:1849–1851.
  • Ioannides, C., Hall, D. E., Mulder, D. E., Steele, C. M., Spickett, J., Delaforge, M., Parke, D. V. (1983). A comparison of the protective effects of N-acetyl-cysteine and S-carboxymethylcysteine against paracetamol-induced hepatotoxicity. Toxicology 28:313–321.
  • Ishibashi, Y., Takayama, G., Inouye, Y., Taniguchi, A. (2010). Carbocisteine normalizes the viscous property of mucus through regulation of fucosylated and sialylated sugar chain on airway mucins. Eur J Pharmacol 641:226–228.
  • Ishiwata, K. I., Nakamura, T., Simada, M., Makiguchi, N. (1989). Production of S-(carboxymethyl)-L-cysteine from serine with tryptophan synthase. J Ferment Bioeng 68:84–87.
  • James, S. P., Needham, D. (1973). Some metabolites of S-pentyl-L-cysteine in the rabbit. Xenobiotica 3:207–218.
  • James, S. P., Jeffery, D. A., Waring, R. H., Wood, P. B. (1968). Some metabolites of 1-bromopropane in the rabbit and rat. Biochem J 109:727–736.
  • Johnson, M. K. (1976). Metabolism of chloroethanol in the rat. Biochem Pharmacol 16:185–199.
  • Jones, B. K., Hathaway, D. E. (1978). The biological fate of vinylidene chloride in rats. Chem Biol Interact 20:27–41.
  • Jones, J. A., Kaphalia, L., Treinen-Moslen, M., Liebler, D. C. (2003). Proteomic characterization of metabolites, protein adducts, and biliary proteins in rats exposed to 1,1-dichloroethylene or diclofenac. Chem Res Toxicol 16:1306–1317.
  • Jones, A. R., Walsh, D. A. (1980). The fate of S-propylcysteine in the rat. Xenobiotica 10:827–834.
  • Joullié, M., Laurre, M., Maillard, G., Muller, P. (1961). Médicament soufré, utilisable en particulier en oto-rhino-laryngologie et an pneumologie. French Patent (Fr. Demande) FR M226 to Recherches et Propagande Scientifiques (February 27, 1961).
  • Joullié, M., Laurre, M., Maillard, G., Muller, P. (1962). Cysteine derivatives. French Patent (Fr. Demande) FR 1,288,907 to Recherches et Propagande Scientifiques (March 30, 1962).
  • Joullié, M., Laurre, M., Maillard, G., Muller P. (1965). Medical uses of S-carboxymethylcysteine. French Patent (Fr. Demande) FR M3111 to Recherches Pharmaceutiques et Scientifiques (March 12, 1965).
  • Jovanovic, D., Cušic, S., Segrt, Z., Dordevic, D., Vehabovic, M., Ptogija, N. (2006). A comparative bioavailability study of generic capsule formulation containing carbocysteine. Die Pharmazie 61:446–449.
  • Kalopissis, G. (1970). Anti-acne skin cosmetics. German Patent (Ger. Offen.) DE 1,930,023 to L’Oréal, Paris, France (January 15, 1970).
  • Kalopissis, G., Manoussos, G. (1969). Antiseborrheic compositions for oral administration. British Patent GB 1,163,870 to L’Oréal, S.A. (September 10, 1969).
  • Kalopissis, G., de Beaulieu, P., Abegg, J.-L., Ghilardi, G. (1972). Treatment of excessive sebaceous glands secretions with substituted cysteamine compounds. U.S. Patent 3,671,643 to L’Oréal, Paris, France (June 20, 1972).
  • Kawaguchi, T., Yamamoto, M. (2000). A case of fixed drug eruption due to carbocysteine that took two days to be provoked. Jpn J Dermatoallergol 8:125–128.
  • Kedderis, G. L., Sumner, S. C., Held, S. D., Batra, R., Turner, M. J., Jr., Roberts, A. E., et al. (1993). Dose-dependent urinary excretion of acrylonitrile metabolites by rats and mice. Toxicol Appl Pharmacol 120:288–297.
  • Khan, S., Mitchell, S. C., Steventon, G. B. (2004). Lack of congruence between cysteine dioxygenase activity and S-carboxymethyl-L-cysteine sulphoxidation activity in rat cytosol. J Pharm Pharmacol 56:993–1000.
  • Kobayashi, K. (1970). Studies on the new metabolites of cystine: 1. Orientation studies on the in vivo formation of S-(carboxymethylthio)cysteine and S-(2-hydroxy-2-carboxyethylthio)cysteine from cystine and related compounds. Physiol Chem Phys 2:455–466.
  • Koch, R., Moenig, H. (1966). Biological radiation protection. LXXIV. Localization and behaviour of radicals in irradiated biochemicals. Strahlenther Onkol 131:289–297.
  • Kodama, H., Ohmori, M., Suzuki, M., Mizuhara, S. (1970). New sulfur-containing amino acids in the urine of cystathioninuric patients: supplementary data. Physiol Chem Phys 2:287–292.
  • Koulbanis, C., Bouillon, C., Darmenton, P. (1978). Cosmetic preparation with slimming and anticellulitis action. German Patent. (Ger. Offen.) DE 2,749,801 to L’Oréal, Paris, France (May 11, 1978).
  • Koulbanis, C., Bouillon, C., Darmenton, P. (1981). Cosmetic compositions having a slimming action. U.S. Patent 4,288,433 to L’Oréal, Paris, France (September 24, 1979).
  • Kubec, R., Dadáková, E. (2009). Chromatographic methods for determination of S-substituted cysteine derivatives—a comparative study. J Chromatogr 1216A:6957–6963.
  • Kubec, R., Kim, S., McKeon, D. M., Musah, R. A. (2002a). Isolation of S-n-butylcysteine sulfoxide and six n-butyl-containing thiosulfinates from Allium siculum. J Nat Prod 65:960–964.
  • Kubec, R., Svobodová, M., Velisek, J. (2002b). Distribution of S-alk(en)ylcysteine sulfoxides in some Allium species. Identification of a new flavour precursor, S-ethylcysteine sufoxide. J Agric Food Chem 48:428–433.
  • Kumagai, H. (2000). Microbial production of amino acids. In: Scheper, T., Fiechter, A. (Eds.), History of modern biotechnology. 1. Advances in biochemical engineering technology (vol. 69, pp. 80). Berlin: Springer-Verlag.
  • Kumagai, H. (2006). Amino acid production. In: Dworkin, M., Falkow, S., Rosenberg, E., Schleifer, K. H., Stackebrandt, E. (Eds.), The prokaryotes: a handbook on the biology of bacteria: symbiotic associations, biotechnology, applied microbiology (vol. 1, p. 758). Singapore: Springer Science.
  • Kumagai, H., Suzuki, H., Shigematsa, H., Tochikura, T. (1989). S-Carboxymethylcysteine synthase from Escherichia coli. Agric Biol Chem 53:2481–2487.
  • Kunert, J. (1981). Organic sources for the growth of the dermatophyte microsporum gypseum. Folia Microbiol 26:201–206.
  • Kupfer, A., Idle, J. R. (1990). False positives with current carbocysteine protocol for sulphoxidation phenotyping. Lancet 335:1107.
  • Kupfer, A., Gerber, F., Maner, E., Turner, I., Idle, J. R. (1991a). Revised protocol for carbocysteine phenotyping in man. Naunyn-Schmiededeberg’s Arch Pharmacol 343:R10 (Abstract No. 38).
  • Kupfer, A., Gerber, F., Hanser, E., Gregory, W., Meese, C. O., Idle, J. R. (1991b). Phenocopy of extensive carbocysteine metabolism by acetyl cysteine co-administration in poor metaboliser subjects. Experientia 47:A29.
  • Lang, G., Malaval, A. (1983). Keratin hydrolysates for hair preparations. French Patent (Fr. Demande) FR 2,529,214 to L’Oréal, Paris, France (December 30, 1983).
  • LaPorte, G. (1968). Antiseborrheic substances: therapeutic or cosmetic applications. Parfumerie Cosmetique Savons 11:516–522.
  • Lebrecque, G., Bélanger, P. M. (1991). Biological rhythms in absorption, distribution, metabolism, and excretion of drugs. Pharmacol Ther 52:95–107.
  • Lerch, S., Kupfer, A., Idle, J. R., Lauterburg, B. H. (2006). Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration. Toxicol Lett 161:188–194.
  • Lévi, F., Schibler, U. (2007). Circadian rhythms: mechanism and therapeutic implications. Annu Rev Pharmacol Toxicol 47:593–628.
  • Lewis, H. B. (1935). The chief sulfur compounds in nutrition. J Nutr 18:225–228.
  • Liebig, J., Poggendorff, J. C., Wöhler, F. (1862). Handwörterbuch der reinen und angewandten chemie, 2nd ed. (vol. 2, pp. 336–337). Braunschweig, Germany: F. Vieweg and Sohn.
  • Lim, F. L., Currie, R. A., Orphanides, G., Moggs, J. G. (2006). Emerging evidence for the interrelationship of xenobiotic exposure and circadian rhythms: a review. Xenobiotica 36:1140–1151.
  • Lombardini, J. B., Singer, T. P., Boyer, P. D. (1969). Cysteine oxygenase. II. Studies on the mechanism of the reaction with 18oxygen. J Biol Chem 244:1172–1175.
  • Lough, S. A., Perilstein, W. L., Heinen, H. J., Carter, L. W. (1941). Cystinuria. The metabolism of cystine, methionine, homocysteine, and S-carboxymethylcysteine. J Biol Chem 139:487–498.
  • Lugo-Vallin, N.., Pascuzzo-Lima, C., Maradei-Irastorza, I., Ramirez-Sanchez, M., Sosa-Sequera, M., Aguero-Pena, R., et al. (2002). Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants. Vet Hum Toxicol 44:40–41.
  • Lugo-Vallin, N., Maradei-Irastorza, I., Pascuzzo-Lima, C., Ramirez-Sanchez, M., Montesinos, C. (2003). Thirty-five cases of S-carboxymethylcysteine use in paraquat poisoning. Vet Hum Toxicol 45:45–46.
  • Lutz, D., Gielsdorf, W., Rasper, J., Jaeger, H., Albring, M., Eisler, G., et al. (1985). The bioavailability and pharmacokinetics of two carbocysteine preparations after single and multiple dosing. Arzneimttel-Forsch 35:163–166.
  • Maccio, A., Meddeddu, C., Panzone, F., Mantovani, G. (2009). Carbocysteine: clinical experience and new perspectives in the treatment of chronic inflammatory diseases. Expert Opin Pharmacother 10:693–703.
  • Magliulo, E., Bonizzoni, D., Cattaneo, E., Scevola, D., Concia, E. (1975). Studies on the clinical effectiveness of the mucolytic drug, S-carboxymethylcysteine, in the therapy of acute and chronic bronchitis. Minerva Med 66:1187–1197.
  • Maignan, J. (2000). Use of carboxylic acids having a sulphur function for promoting skin exfoliation or stimulating epidermal growth. U.S. Patent 6,153,649 to L’Oréal, Paris, France (November 28, 2000).
  • Marcet, A. (1817). An essay on the chemical history and medical treatment of calculous disorders (pp. 79–88). London: Longman, Hurst, Rees, Orme and Brown.
  • Maynard, W. R., Bruce, R. B., Fox, G. G. (1978). Determination of carbocysteine from human plasma. J Pharm Sci 67:1735–1755.
  • McCormack, F. X., Jr. (2007). Peptides with antioxidant and antimicrobial properties. U.S. Patent 7,273,847 to University of Cincinnati and the National Institutes of Health, Bethesda, Maryland, USA (September 25, 2007).
  • Meek, D. W., Straub, D. K., Drago, R. S. (1960). Transition metal ion complexes with dimethyl sulphoxide. J Amer Chem Soc 82:6013–6016.
  • Meese, C. O. (1991). Studies on the metabolism of carboxymethylcysteine in man. COST B1 meeting report (October 29, 1991). Brussels: Office for Official Publications of the European Communities.
  • Meese, C. O., Fischer, C., Kupfer, A., Wisser, H., Eichelbaum, M. (1991). Identification of the “major” polymorphic carbocysteine metabolite as S-(carboxymethylthio)-L-cysteine. Biochem Pharmacol 42:R13–R16
  • Meese, C. O., Specht, D., Ratge, D., Eichelbaum, M., Wisser, H. (1993). High-performance liquid chromatographic and carbon-13 nuclear magnetic resonance spectrometric determinations of S-carboxymethyl-L-cysteine and its metabolites in human urine. Fresenius J Anal Chem 346:837–840.
  • Meese, C. O., Specht, D., Hofmann, U., Fischer, P., Eichelbaum, M., Wisser, H. (1989). An ex vivo carbon-13 NMR study on the metabolism of S-carboxymethyl-L-cysteine in man—a reinvestigation [PP02-68] [abstract]. Eur J Clin Pharmacol 36(Suppl.):A151.
  • Michaelis, L., Schubert, M. P. (1934). The reaction of iodoacetic acid on mercaptans and amines. J Biol Chem 106:331–341.
  • Mitchell, S. C., Steventon, G. B. (2006a). Drug metabolism and toxicity: hijacking enzymes of intermediary metabolism. Curr Topics Toxicol 3:57–63.
  • Mitchell, S. C., Steventon, G. B. (2006b). Carbocisteine therapy in older people with chronic pulmonary obstructive pulmonary disease. J Am Geriatr Soc 54:1792–1793.
  • Mitchell, S. C., Steventon, G. B. (2009). Foreign compounds and intermediary metabolism: sulfoxidation bridges the divide. Curr Drug Metab 10:220–226.
  • Mitchell, S. C., Smith, R. L., Waring, R. H., Aldington, G. F. (1984a). The metabolism of S-methyl-L-cysteine in man. Xenobiotica 14:767–779.
  • Mitchell, S. C., Waring, R. H. (1989a). The deficiency of sulfoxidation of S-carboxymethyl-L-cysteine. Pharmac Ther 43:237–249.
  • Mitchell, S. C., Waring, R. H. (1989b). S-Oxygenases. III: Human pharmacogenetics. In: Damani, L. A. (Ed.), Sulphur-containing drugs and related organic compounds (vol. 2A, pp. 101–119). Chichester, UK: Ellis Horwood Ltd.
  • Mitchell, S. C., Waring, R. H., Haley, C. S., Idle, J. R., Smith, R. L. (1984b). Genetic aspects of the polymodally distributed sulphoxidation of S-carboxymethyl-L-cysteine in man. Brit J Clin Pharmacol 18:507–521.
  • Mitchell, S. C., Waring, R. H., Land, D., Thorpe, W. V. (1987). Odorous urine following asparagus ingestion in man. Experientia 43:382–383.
  • Mitchell, S. C., Waring, R. H., Steventon, G. B. (1992). Variation in the S-oxidation of cysteine derivatives. In: Kalow, W. (Ed.), Pharmacogenetics of drug metabolism (pp. 367–382). New York: Pergamon.
  • Mitchell, S. C., Waring, R. H., Wilson, V. L., Idle, J. R., Autrup, H., Harris, C. C., et al. (1986). Sulphoxidation of S-carboxymethyl-L-cysteine in the Rhesus monkey (Macaca mulatta), Cynomologus monkey (Macaca fascicularis), African Green monkey (Cercopithecus aethiops), and the marmoset (Callithrix jacchus). Comp Biochem Physiol 84B:143–144.
  • Miura, J., Yasuda, K., Ito, M., Ito, M. (1995). Separation column containing S-carboxymethylcysteine. U.S. Patent 5,407,568 to Hitachi Ltd, Tokyo, Japan (April 18, 1995).
  • Moeller, H., Wallat, S. (1982). Aryl and heteroarylmercaptoalkanoic acid derivatives as antiseborrhoeic additives for cosmetic compositions. German Patent (Ger. Offen.) DE 3,121,072 (December 16, 1982).
  • Mueller, J. H. (1921). Growth-determining substances in bacteriological culture media. Proc Soc Exp Biol Med 18:225–228.
  • Mueller, J. H. (1922). A new sulfur-containing amino acid isolated from casein. Proc Soc Exp Biol Med 19:161–163.
  • Mueller, J. H. (1923). A new sulfur-containing amino acid isolated from hydrolytic products of protein. J Biol Chem 56:157–169.
  • Müller, G., Norpoth, K. (1975). Bestimmung zweier Urinmetabolite des Vinylchlorids. Naturwissenschaften 62:541.
  • Müller, G., Norpoth, K., Eckard, R. (1976). Identification of two urine metabolites of vinyl chloride by GC-MS-investigations. Int Arch Occup Environ Health 38:69–75.
  • Müller, G., Norpoth, K., Eckard, R. (1979). Identification of S-(carboxymethyl)-L-cysteine and thiodiglycollic acid, urinary metabolites of 2,2′-bis(chloroethyl)ether in rat. Cancer Lett 7:299–305.
  • Müller, F. O., van Achterbergh, S. M., Hundt, H. K. L. (1983). Paracetamol overdose: protective effect of concomitantly ingested antimuscarinic drugs and codeine. Hum Toxicol 3:473–477.
  • Munck, L. K., Munck, B. G. (1995). Amino acid transport in the small intestine. Physiol Rev 44:335–346.
  • Murray, T. F., Allan, J. V. A. (1958). Carboxymethylmercapto compounds as stabilizers for photographic emulsions. U.S. Patent 2,819,965 to Eastman Kodak Co. (January 14, 1958).
  • Navrátil, T., Petr, M., Šenholdová, Z., Přistoupilová, K., Přistoupil, T. I., Heyrovský, M., et al. (2007). Diagnostic significance of urinary thiodiglycolic acid as a possible tool for studying the role of vitamins B12 and folates in the metabolism of thiolic substances. Physiol Res 56:113–122.
  • Ndour, C. T., Ahmed, K., Nakagawa, T., Nakano, Y., Ichinose, A., Tarhan, G., et al. (2001). Modulating effects of mucoregulatory drugs on the attachment of Haemophilus influenzae. Microb Pathog 30:121–127.
  • Nedeljković, J. M., Vasić, V. M., Vuković, V. V., Jovanović, T. S. (1995). Kinetics of the reaction of S-carboxymethyl-L-cysteine with palladium(II) chloride. J Pharm Biomed Anal 13:471–475.
  • Niederwiesser, A., Giliberti, P., Baerlocher, K. (1973). β-Mercaptolactate cysteine disufiduria in two normal sisters. Isolation and characterization of β-mercaptolactate cysteine disulfide. Clin Chim Acta 43:405–416.
  • Panagopoulos, P. (2008). The metabolism and pharmacokinetics of S-carboxymethyl-L-cysteine in large mammalian species. Ph.D. Thesis. University of London, UK.
  • Panagopoulos, P., Forbes, B., Mitchell, S. C., Steventon, G. B. (2010). The pharmacokinetics of orally administered S-carboxymethyl-L-cysteine in the dog, calf, and sheep. Eur J Pharmaceut Sci 39:219–223.
  • Parkes, E. A. (1860). The composition of urine, in health and disease, and under the action of remedies (pp. 360–363). London: John Churchill.
  • Patel, N. G., Iliadou, C., Boonyapiwat, B., Barlow, D. J., Forbes, B., Mitchell, S. C., et al. (2008). Enzyme kinetic and molecular modelling studies on sulphur-containing substrates of phenylalanine 4-monooxygenase. J Enzyme Inhibit Med Chem 23:958–963.
  • Payan, J. P., Beydon, D., Fabry, J. P., Brondeau, M. T., Ban, M., de Ceaurriz, J. (1993). Urinary thiodiglycolic acid and thioether excretion in male rats dosed with 1,2-dichloroethane. J Appl Toxicol 13:417–422.
  • Pierson, E., Tishler, M. (1949a). α-Amino-β-(carboxymethylmercapto)propionic acid from cystine. U.S. Patent 2,460,785 to Merck & Co. (February 1, 1949).
  • Pierson, E., Tishler, M. (1949b). α-Amino-β-(carboxymethylmercapto)propionic acid from cystine. British Patent GB 632,682 to Merck & Co. (November 28, 1949).
  • Pignataro, O., Pignataro, L. D., Gallus, G., Calori, G., Cordaro, C. I. (1996). Otitis media with effusions and S-carboxymethylcysteine and/or its lysine salt: a critical overview. Int J Pediatr Otorhinolaryngol 35:231–241.
  • Pirie, N. W. (1932). CCXLIII. Studies in the sulfur metabolism of the dog. XI. The metabolism of methionine and related sulphides. Biochem J 26:2041–2045.
  • Poole, P. J., Black, P. N. (2001). Oral mucolytic drugs for exacerbations of chronic obstructive pulmonary disease: systematic review. Br Med J 322:1–6.
  • Preston, J. S., du Preez, A. C. (2001). Solvent extraction of trivalent lanthanides and yttrium from nitrate media by dialkyl sulphoxides. Solv Extrac Ion Exch 19:581–595.
  • Preston, J. S., du Preez, A. C. (2002). Solvent extraction of platinum-group metals from hydrochloric acid solutions dialkyl sulphoxides. Solv Extract Ion Exch 20:359–374.
  • Prout, W. (1840). On the nature and treatment of stomach and urinary diseases: being an inquiry into the connexion of diabetes, calculus, and other affections of the kidney and bladder with indigestion, 3rd ed. (pp. 231–240). London: John Churchill.
  • Quastel, J. H., Wheatley, A. H. M. (1932). The relation of thiol compounds to glucose formation. Biochem J 26:2169–2176.
  • Quevauviller, A., Huyen, V. N., Garcet, S., Lakah, L. (1967). Activité des mucolytiques sur le rétention experimentale du mucus intrabronchique chez le rat. Therapie 22:485–493.
  • Ramirez-Sanchez, M., Pacheco, F. J., Gómez, P. N., Fuentes, S. (2008). Intoxicación pediátrica por fósforo blanco (saltapericas). Supervivencia a ingesta de dosis potencialmente letal. Arch Venez Puer Ped 71:140–144.
  • Ramirez-Sanchez, M. S., Pascuzzo-Lima, C., Bastidis, O. (2009). Tratamiento de intoxicaciones por compuestos hepatotóxicos: uso de la N-acetilcisteína y las carboximetilcisteína. Arch Venez Puer Ped 72:68–72.
  • Rapkine, L. (1933). Sur l’action de l’acide monoiodacétique sur le glutathion et la cystéine. C R Séanc Soc Biol 112:790–792.
  • Ravella, R., Komarmeni, S., Martinez, C. E. (2008). Highly charged swelling mica-type clays for selective Cu exchange. Environ Sci Technol 42:113–118.
  • Reddy, A. S., Reddy, M. L. (1983). Extraction of silver with sulfoxides from thiocyanate media. Radiochem Radioanalyt Lett 59:133–137.
  • Reichert, D., Werner, H. W., Metzler, M., Henschler, D. (1979). Molecular mechanisms of 1,1-dichloroethylene toxicity: excreted metabolites reveal different pathways of reactive intermediates. Arch Toxicol 42:159–169.
  • Rinaldi, A., Fadda, M. B., Piccaluga, G., De Marco, C. (1973). Oxidation of S-carboxymethylcysteine by D-aspartate oxidase. Ital J Biochem 22:46–54.
  • Rogers, K. M., Barnsley, E. A. (1977). The metabolism of S-carboxyalkylcysteines in man. Xenobiotica 7:409–414.
  • Rose, R. A., Shiple, G. J., Sherwin, C. P. (1924). The oxidation of cystine and cysteine in the animal organism. Am J Physiol 69:518–530.
  • Rozen, A. M., Murinov, Y. I., Nikitin, Y. E., Teterin, E. G., Kaminskaya, L. K., Mazalov, L. N., et al. (1973). Extraction capability of sulfoxides. VIII. Coordination of metals by sulfoxides. Radiokhimiya 1:123–125.
  • Sano, K., Yokozeki, K., Tamura, F., Yasuda, N., Noda, I., Mitsugi, K. (1977). Microbial conversion of DL-2-amino-Δ2-thiazoline-4-carboxylic acid to L-cysteine and L-cystine: screening of microorganisms and identification of products. Appl Environ Microbiol 34:806–810.
  • Sanofi-Aventis. (2008). Mucodyne 375mg capsules: summary of product characteristics (SPC). Available at: http://www.medicines.ie/medicine/3908/SPC/Mucodyne+375mg+Capsules/#PHARMACOKINETICS. Accessed on February 16, 2011.
  • Schmutz, J. L., Barbaud, A., Trechot, P. (2005). Fixed drug eruption and carbocysteine. Ann Dermatol Venereol 132:403.
  • Servin, A. (1977). Demonstration of an enterohepatic cycle for S-carboxymethylcysteine. C R Séanc Soc Biol 171:39–42.
  • Servin, A., Garcet, S., Huyen, V. N., Cohen, Y. (1976). Pharmacocinetique compare de la L-cysteine et de l’un de ses derives S-substitue, la S-carboxymethyl-L-cysteine. J Pharmacol 7:275–286.
  • Servin, A., Garcet, S., Huyen, V. N. (1974). Bronchopulmonary uptake of sulfur from carboxymethylcysteine-35S and cysteine-35S in normal rats and in rats exposed to sulfur dioxide. Effects of prolonged administration of these two sulfur-containing molecules on bronchopulmonary lesions and on pulmonary uptake of their sulfur. Bull Physio-Pathol Respir 10:315–329.
  • Servin, A., Garcet, S., Huyen, V. N., Muller, P., Cohen, Y. (1972). Tissular distribution of sulfur-35 as a function of time after oral administration of carboxymethylcysteine-35S. Autoradiography and pharmacokinetics. C R Séanc Soc Biol 166:543–548.
  • Servin, A., Garcet, S., Huyen, V. N., Cohen, Y. (1976). Comparative pharmacokinetics of L-cysteine and one of its S-substituted derivatives, S-carboxymethyl-L-cysteine. J Pharmacol 7:275–286.
  • Sklan, N. M., Barnsley, E. A. (1968). The metabolism of S-methyl-L-cysteine. Biochem J 107:217–223.
  • Staffeldt, B., Brockmoller, J., Roots, I. (1990). Evaluation of possible polymorphisms in sulfoxidation of carbocystein analysed by HPLC-methods. Eur J Pharmacol 183:627–628.
  • Staffeldt, B., Brockmoller, J., Roots, I. (1991). Determination of S-carboxymethyl-L-cysteine and some of its metabolites in urine and serum by high-performance liquid chromatography using fluorescent pre-column labelling. J Chromatogr Biomed Appl 571:133–147.
  • Stekol, J. A. (1947). Synthesis of S(carboxymethyl)homocysteine and S-(2-carboxyethyl)homocysteine and a study of their availabilities for growth of rats maintained on a low-casien diet. Arch Biochem 13:127–130.
  • Steventon, G. B. (1998). A methodological and metabolite identification study of the metabolism of S-carboxymethyl-L-cysteine in man. Chromatographia 48:561–568.
  • Steventon, G. B. (1999a). Diurnal variation in S-oxidation of S-carboxymethyl-L-cysteine metabolism in man. Biochem Soc Trans 27(A121):114.
  • Steventon, G. B. (1999b). Diurnal variation in the metabolism of S-carboxymethyl-L-cysteine in humans. Drug Metab Dispos 27:1092–1097.
  • Steventon, G. B., Mitchell, S. C. (2006a). Non-classical drug metabolism enzymes: the curious case of phenylalanine 4-monooxygenase. Lett Drug Design Discov 3:405–412.
  • Steventon, G. B., Mitchell, S. C. (2006b). The sulphoxidation of S-carboxymethyl-L-cysteine in COPD. Eur Respir J 27:865–866.
  • Steventon, G. B., Mitchell, S. C. (2006c). Efficacy of S-carboxymethyl-L-cysteine for otitis media with effusions. ENT J 85:296–297.
  • Steventon, G. B., Mitchell, S. C. (2009a). Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates. J Biochem Mol Toxicol 23:119–124.
  • Steventon, G. B., Mitchell, S. C. (2009b). Phenylalanine 4-monooxygenase and the role of endobiotic enzymes in xenobiotic transformation. Expert Opin Drug Metab Toxicol 5:1213–1221.
  • Steventon, G. B., Mitchell, S. C., Angulo, S., Barbas, C. (2011). An investigation into possible xenobiotic-endobiotic inter-relationships involving the amino acid analogue drug, S-carboxymethyl-L-cysteine, and plasma amino acids in humans. Amino Acids May 10. [Epub ahead of print]
  • Steventon, G. B., Sturman, S., Waring, R. H., Williams, A. C. (2001). A review of xenobiotic metabolism enzymes in Parkinson’s and motor neurone disease. Drug Metab Drug Interact 18:79–98.
  • Steventon, G. B., Mitchell, S. C., Pérez, B., Desviat, L. R., Ugarte, M. (2009). The activity of wild type and mutant phenylalanine hydroxylase with respect to the C-oxidation of phenylalanine and the S-oxidation of S-carboxymethyl-L-cysteine. Mol Genet Metab 96:27–31.
  • Suer, E., Savrac, S., Sarinav, E., Ozturk, H. E., Turkoz, M., Nagatake, T., et al. (2008). Variation in the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells after treatment with S-carboxymethylcysteine. J Infect Chemother 14:333–336.
  • Sun, L., Tang, L., Xu, Y., Wang, S., Li, Y., Kang, J. (2010). The effect and mechanism of action of carbocysteine on airway bacterial load in rats chronically exposed to cigarette smoke. Respirology 15:1064–1071.
  • Tapley, D. F., Herz, R., Jr., Ross, J. E., Deuel, T. F., Leventer, L. (1960). Glucuronide formation in the active transport of amino acid and thyroxine analogues by rat intestine. Biochim Biophys Acta 43:344–345.
  • Tardiff, R., Goyal, R., Brodeur, J., Gerin, M. (1987). Species differences in the urinary disposition of some metabolites of ethylene oxide. Fund Appl Toxicol 9:448–453.
  • Tarver, H., Schmidt, C. L. A. (1939). The conversion of methionine to cystine: experiments with radioactive sulfur. J Biol Chem 130:67–80.
  • Thalow, M. J. C. (1838a). Ueber die Zusammensetzung des Blasenoxyds (Cystic Oxyd) Justus Liebigs Ann Chem 27:197–201.
  • Thalow, M. C. J. (1838b). Sur la composition de la cystine. J Pharm 24:629–632.
  • Thompson, M. L., Pavia, D., Jones, C. J., McQuisten, T. A. (1975). No demonstrable effect of S-carboxymethylcysteine on clearance of secretions from the human lung. Thorax 30:669–673.
  • Thomson, T. (1843). Chemistry of animal bodies (pp. 105–107). Edinburgh: Adam and Charles Black. London: Longman, Brown, Green and Longmans.
  • Thorpe, S. R., Baynes, J. W. (2003). Maillard reaction products in tissue proteins: new products and new perspectives. Amino Acids 25:275–281.
  • Thudichum, J. L. W. (1858). A treatise on the pathology of the urine (pp. 295–297). London: J. Churchill.
  • Troonen, H., Roelants, P., Boon, B. (1976). RIT 2214, a new biosynthetic penicillin produced by a mutant of Cephalosporium acremonium. J Antibiot (Tokyo) 29:1258–1267.
  • Turnbull, L. B., Teng, L., Kinzie, J. M., Pitts, J. E., Pinchbeck, F. M., Bruce, R. B. (1978). Excretion and biotransformation of carboxymethylcysteine in rat, dog, monkey, and man. Xenobiotica 10:621–628.
  • Ubuka, T., Kobayashi, K., Yao, K., Kodama, H., Fujii, K., Hirayama, K., et al. (1968). S-(2-hydroxy-2-carboxyethylthio)cysteine and S-(carboxymethylthio)cysteine in human urine. Biochim Biophys Acta 158:493–495.
  • Ubuka, T., Kodama, H., Mizuhara, S. (1967). Isolation of S-(carboxymethyl)cysteine from urine. Biochim Biophys Acta 141:266–269.
  • Van Achterbergh, S. M., Müller, F. O., Steyn, J. M. (1982). Massive paracetamol overdose: fatal liver damage prevented by administration of S-carboxymethyl-L-cysteine [abstract]. S Afr J Sci 78:171.
  • Vinas, A. B. (1986). Zinc carbocysteinate. U.S. Patent 4,618,625 to Laboratorios Vinas, S.A., Barcelona, Spain (October 21, 1986).
  • Visarius, T. M., Bahler, H., Kupfer, A., Cerny, T., Lauterburg, B. H. (1998). Thiodiglycolic acid is excreted by humans receiving ifosfamide and inhibits mitochondrial function in rats. Drug Metab Dispos 26:193–196.
  • Walash, M. I., El-Brashy, A. M., Metwally, M. E., Abdelal, A. A. (2004). Spectrophotometric determination of penicillamine and carbocisteine based on formation of metal complexes. Il Farmaco 59:493–503.
  • Walchner, F. A. (1826). Chemische Untersuchung eines Harnsteins. J Chem Physik (Schweigger) 47:106–109.
  • Walchner, F. A. (1827). Chemische Untersuchung eines Harnsteins aus Blasenoxyd. Arch Pharm 21:176–177.
  • Waring, R. H. (1978). The metabolism of S-carboxymethylcysteine in rodents, marmosets and man. Xenobiotica 8:265–270.
  • Waring, R. H. (1980). Variation in human metabolism of S-carboxymethylcysteine. Eur J Drug Metab Pharmacokinet, 5, 49–52.
  • Waring, R. H, Mitchell SC. (1982). The metabolism of S-carboxymethyl-L-cysteine in man. Drug Metab Dispos, 10, 61–62.
  • Waring, R. H., Mitchell, S. C. (1990). Carbocysteine sulphoxidation phenotype. Lancet 335:1527.
  • Waring, R. H., Mitchell, S. C., Idle, J. R., Smith, R. L. (1981). Genetically determined impaired drug sulphoxidation. Lancet 1:778.
  • Waring, R. H., Mitchell, S. C., O’Gorman, J., Fraser, M. (1986). Cytosolic sulphoxidation of S-carboxymethyl-L-cysteine in mammals. Biochem Pharmacol 35:2999–3002.
  • Waring, R. H., Mitchell, S. C., Shah, R. R., Idle, J. R., Smith, R. L. (1982). Polymorphic sulphoxidation of S-carboxymethyl-L-cysteine in man. Biochem Pharmacol 31:3151–3154.
  • Waring, R. H., Mitchell, S. C., Shah, R. R. (1983). The metabolism of S-carboxymethyl-L-cysteine in man: isolation of an ester glucuronic acid conjugate from urine. Xenobiotica 13:311–317.
  • Waring, R. H., Harris, R. M., Steventon, G. B., Mitchell, S. C. (2003). Degradation to sulphate of S-methyl-L-cysteine sulphoxide and S-carboxymethyl-L-cysteine sulphoxide in man. Drug Metab Drug Interact 19:241–255.
  • Waterhouse, J. M., Minors, D. S. (1989). Temporal aspects of renal drug elimination. In: Lemmer, B. (Ed.), Chronopharmacology: cellular and biochemical interactions (pp. 35–50). New York: Marcel Dekker.
  • Watson, R. G. P., Olomu, A., Clements, D., Waring, R. H., Mitchell, S. C., Elias, E. (1988). A proposed mechanism for chlorpromazine jaundice—defective hepatic sulphoxidation combined with rapid hydroxylation. J Hepatol 7:72–78.
  • Westerman, B. D., Rose, W. C. (1928). The oxidation of disulfide acids in the animal organism. J Biol Chem 79:423–428.
  • Wetli, H. A., Brenneisen, R., Tschudi, I., Langos, M., Bigler, P., Sprang, T., et al. (2005). A gamma-glutamyl peptide isolated from onion (Allium cepa L.) by bioassay-guided fractionation inhibits resorption activity of osteoclasts. J Agric Food Chem 53:3408–3414.
  • Wollaston, W. H. (1800–1814). On cystic oxide, a new species of urinary calculus (abstract). Abstr Phil Trans Roy Soc 1:376–377.
  • Wollaston, W. H. (1810a). On cystic oxide, a new species of urinary calculus. Phil Trans Roy Soc 100:223–230.
  • Wollaston, W. H. (1810b). De l’oxide cystique, espèce nouvelle de calcul. Justus Liebigs Ann Chem 76:21–33.
  • Wollaston, W. H. (1812). Eine neue Art Harnstein unter den Namen Blasenoxyd (oxyde cystique) beschrieben. J Chem Physik (Schweigger) 4:193–197.
  • Woolfson, A. D., Millership, J. S., Karim, F. I. A. (1987). Determination of the sulphoxide metabolites of S-carboxymethyl-L-cysteine by high performance liquid chromatography with electrochemical detection. Analyst 112:1421–1425.
  • Wormhoudt, L. W., Commandeur, J. N., Ploemen, J. H., Abdoelgafoer, R. S., Makansi, A., van Bladeren, P. J., et al. (1997). Urinary thiodiacetic acid. A selective biomarker for the cytochrome P450-catalysed oxidation of 1,2-dibromoethane in the rat. Drug Metab Dispos 25:508–515.
  • Wormhoudt, L. W., Hissink, A. M., Commandeur, J. N. M., van Bladeren, P. J., Vermeulen, N. P. E. (1998). Disposition of 1,2-[14C]dibromoethane in male Wistar rats. Drug Metab Dispos 26:437–447.
  • Xie, T., Marshall, W. D. (2001). Approaches to soil remediation by complexometric extraction of metal contaminants with regeneration of reagents. J Environ Monitor 3:411–416.
  • Xu, Z., Yu, R., Gu, G., Chen, Z. (2007). Study on extraction mechanism of palladium and platinum with sulfoxide BSO. Guijinshu 28:6–9.
  • Yamaguchi, K., Hosokawa, Y. (1987). Cysteine dioxygenase. In: Jakoby, W. B., Griffiths, O. W. (Eds.), Sulfur and sulfur amino acids: methods in enzymology (vol. 143, pp. 395–403). London: Academic.
  • Yamaya, M, Nishimura, H, Shinya, K, Hatachi, Y, Sasaki, T, Yasuda, H, et al. (2010). Inhibitory effects of carbocisteine on type A seasonal influenza virus infection in human airway epithelial cells. Am J Physiol Lung Cell Mol Physiol 299:L160–L168.
  • Yanaura, S., Yamatake, Y., Ishikawa, S., Sakamoto, M., Sasagawa, S., Tagashira, E., et al. (1976). Pharmacological studies on a new mucolytic expectorant, S-carboxymethylcysteine. Oyo Yakuri 12:777–788.
  • Yasuda, H., Yamaya, M., Sasaki, T., Inoue, D., Nakayama, K., Tomita, N., et al. (2006a). Carbocisteine reduces frequency of common colds and exacerbations in patients with chronic obstructive pulmonary disease. J Am Geriatr Soc 54:378–380.
  • Yasuda, H., Yamaya, M., Sasaki, T., Inoue, D., Nakayama, K., Yamada, M., et al. (2006b). Carbocisteine inhibits rhinovirus infection in human tracheal epithelial cells. Eur Respir J 28:51–58.
  • Yeh, Y. Y., Liu, L. (2001). Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies. J Nutr 131:989–S993S.
  • Yelloly, J. (1829). VIII. Remarks on the tendency to calculus diseases with observations on the nature of urinary concretions, and an analysis of a large part of the collection belonging to the Norfolk and Norwich Hospital. Phil Trans Roy Soc 119:55–81.
  • Yllner, S. (1971a). Metabolism of chloroacetate-1-14C in the mouse. Acta Pharmacol Toxicol 30:69–80.
  • Yllner, S. (1971b). Metabolism of 1,2-dichloromethane-14C in the mouse. Acta Pharmacol Toxicol 30:275–265.
  • Yosypchuk, B., Novotný, L., Heyrovský, M., Sokolová, R., Hromadová, M., Pospíšil, L., et al. (2004). Electrochemical studies of biologically important systems. In: Brillas, E., Cabot, J. (Eds.), Trends in electrochemistry and corrosion at the beginning of the 21st century (pp. 553–569). Barcelona, Spain: Universitat de Barcelona.
  • Yukawa, H. (1999). Asymmetric synthesis of S-carboxymethyl-L-cysteine by a chemico-enzymatic method. Agric Biol Chem 52:2367–2368.
  • Zeng, J, Davies, M. J. (2005). Evidence for the formation of adducts and S-(carboxymethyl) cysteine on reaction of α-dicarbonyl compounds with thiol groups on amino acids, peptides, and proteins. Chem Res Toxicol 18:1232–1241.
  • Zeng, J, Dunlop, R. A., Rodgers, K. J., Davies, M. J. (2006). Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols. Biochem J 398:197–206.
  • Zheng, C. H., Ahmed, K., Rikitami, N., Martinez, G., Nagatake, T. (1999). The effects of S-carboxymethylcysteine and N-acetylcysteine on the adherence of Moraxella catarrhalis to human pharangeal epithelial cells. Microbiol Immunol 43:107–113.
  • Zheng, J. P., Kang, J., Huang, S. G., Chen, P., Yao, W. Z., Yang, L., et al. (2008). Effect of carbocisteine on acute exacerbations of chronic obstructive pulmonary disease (PEACE Study): a randomised placebo-controlled study. Lancet 371:2013–2018.
  • Ziegler, D. M. (1980). Microsomal flavin-containing monooxygenase: oxygenation of nucleophilic nitrogen and sulfur compounds. In: Jakoby, W. B. (Ed.), Enzymatic basis of detoxication (vol. 1, pp. 201–227). New York: Academic.
  • Ziegler, D. M. (1989). S-Oxygenases. I: Chemistry and biochemistry. In: Damani, L. A. (Ed.), Sulphur-containing drugs and related organic compounds (vol. 2A, pp. 53–66). Chichester, UK: Ellis Horwood Ltd.
  • Ziment, I. (1983a). Gastric stimulation and secretion of mucus. Br Med J (Clin Res Edn) 287:1630.
  • Ziment, I. (1983b). Lung diseases and gastrointestinal disease. Trop Gastrointest Dis 4:57–66.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.