A patent review on the development of human cytochrome P450 inhibitors

Bibliography

• Lewis D, Ito Y. Cytochrome P450 structure and function: an evolutionary perspective. Royal Soc of Chemistry, UK; 2008
   Google Scholar
• Isin EM, Guengerich FP. Complex reactions catalyzed by cytochrome P450 enzymes. Biochim Biophys Acta 2007;1770:314-29
   PubMed Web of Science ®Google Scholar
• Sligar SG, Makris TM, Denisov IG. Thirty years of microbial P450 monooxygenase research: peroxo-heme intermediates—The central bus station in heme oxygenase catalysis. Biochem Biophys Res Commun 2005;338:346-54
   PubMedGoogle Scholar
• Gelboin HV, Gonzalez FJ, Yang TJ; Inventors. Agents that bind to and inhibit human cytochrome P450 1A2. US6335428; 2002
   Google Scholar
• Melvin WA, Murray GIA; Inventors. Antibodies specific for CYP1B1. US7419794; 2008
   Google Scholar
• Nishimura M, Yaguti H, Yoshitsugu H, et al. Tissue distribution of mRNA expression of human cytochrome P450 isoforms assessed by high-sensitivity real-time reverse transcription PCR. Yakugaku Zasshi 2003;123:369-75
   PubMed Web of Science ®Google Scholar
• Tyndale RF. Genetic variation in CYP2A6-mediated nicotine metabolism alters smoking behavior. Ther Drug Monit 2002;24:163
   PubMed Web of Science ®Google Scholar
• Arınç E. The role of polymorphic cytochrome P450 enzymes in drug design, development and drug interactions with a special emphasis on phenotyping. J Mol Catal B-Enzym 2010;64:120-2
   Web of Science ®Google Scholar
• Gelboin HV, Gonzalez FJ; Inventors. Agents that bind to and inhibit human cytochrome P450 2A6. US6323325; 2001
   Google Scholar
• Gelboin HV, Krausz KW, Gonzalez FJ; Inventors. Agents that bind to and inhibit human cytochrome P450 2C8, 2C9, 2C18 and 2C19. US6623960; 2003
   Google Scholar
• Gelboin HV, Krausz KW, Gonzalez FJ; inventors. Antibodies that bind to and inhibit human cytochrome P450 2C9*1, 2C9*2, and 2C9*3. US7524939; 2009
   Google Scholar
• Gelboin HV, Krausz KW, Gonzalez FJ; inventors. Agents that bind to and inhibit human cytochrome P450 2C19. US6908738; 2005
   Google Scholar
• Cook Sangar M, Anandatheerthavarada HK, Tang W, et al. Human liver mitochondrial cytochrome P450 2D6 – individual variations and implications in drug metabolism. FEBS J 2009;276:3440-53
   PubMedGoogle Scholar
• Gelboin HV, Gonzalez FJ, Krausz KW; Inventors. Agents that bind to and inhibit human cytochrome P450 2D6. US6060253; 2000
   Google Scholar
• Gelboin HV, Gonzalez FJ; Inventors. Inhibitory and non-inhibitory antigen binding polypeptides against human P450 enzymes. US5939530; 1999
   Google Scholar
• Lu AY, Wang RW; Inventors. Anti-peptide antibody against human cytochrome P450 3A4. US6300476; 2001
   Google Scholar
• Parise RA, Egorin MJ, Kanterewicz B, et al. CYP24, the enzyme that catabolizes the antiproliferative agent vitamin D, is increased in lung cancer. Int J Cancer 2006;119:1819-28
   PubMed Web of Science ®Google Scholar
• Jones G, Strugnell SA, Deluca HF. Current Understanding of the Molecular Actions of Vitamin D. Physiol Rev 1998;78:1193-231
   PubMed Web of Science ®Google Scholar
• Posner G, Kahraman M, Jeon HB, et al. Inventors. Low-calcemic oxime analogs of 1α,25-dihydroxy vitamin D3. US6982258; 2006
   Google Scholar
• Posner GH, Crawford K, Yang HW, et al. Inventors. 24-Sulfur-substituted analogs of 1α,25-dihydroxy vitamin D3. US7166585; 2007
   Google Scholar
• Kahraman M, Sinishtaj S, Dolan PM, et al. Potent, selective and low-calcemic inhibitors of CYP24 hydroxylase: 24-sulfoximine analogues of the hormone 1α,25-dihydroxyvitamin D3. J Med Chem 2004;47:6854-63
   PubMed Web of Science ®Google Scholar
• Stoppie P, Borgers M, Borghgraef P, et al. R115866 inhibits all-trans-retinoic acid metabolism and exerts retinoidal effects in rodents. J Pharmacol Exp Ther 2000;293:304-12
   PubMed Web of Science ®Google Scholar
• Njar VC, Gediya L, Purushottamachar P, et al. Retinoic acid metabolism blocking agents (RAMBAs) for treatment of cancer and dermatological diseases. Bioorg Med Chem 2006;14:4323-40
   PubMed Web of Science ®Google Scholar
• Thatcher JE, Isoherranen N. The role of CYP26 enzymes in retinoic acid clearance. Expert Opin Drug Metab Toxicol 2009;5:875-86
   PubMed Web of Science ®Google Scholar
• Gomaa MS, Armstrong JL, Bobillon B, et al. Novel azolyl-(phenylmethyl)]aryl/heteroarylamines: potent CYP26 inhibitors and enhancers of all-trans retinoic acid activity in neuroblastoma cells. Bioorg Med Chem 2008;16:8301-13
   PubMed Web of Science ®Google Scholar
• Freyne E, Raeymaekers A, Venet M, et al. Synthesis of Liazal (TM), a retinoic acid metabolism blocking agent (RAMBA) with potential clinical applications in oncology and dermatology. Bioorg Med Chem Lett 1998;8:267-72
   PubMedGoogle Scholar
• Vasudevan J, Johnson AT, Wang L, et al. Inventors. Compounds having activity as inhibitors of cytochrome P450RAI. US6252090; 2001
   Google Scholar
• Vasudevan J, Johnson AT, Wang L, et al. Inventors. Compounds having activity as inhibitors of cytochrome P450RAI. US6399774; 2002
   Google Scholar
• Johnson AT, Vasudevan J, Wang L, et al. Inventors. Compounds having activity as inhibitors of cytochrome P450RAI. US6369261; 2002
   Google Scholar
• Vasudevan J, Johnson AT, Chandraratna RA; Inventors. Compounds having activity as inhibitors of cytochrome P450RAI. US6303785; 2001
   Google Scholar
• Vasudevan J, Johnson AT, Wang L, et al. Inventors. Compounds having activity as inhibitors of cytochrome P450RAI. US6713647; 2004
   Google Scholar
• Vasudevan J, Johnson AT, Wang L, et al. inventors. Compounds having activity as inhibitors of cytochrome P450RAI. US6387951; 2002
   Google Scholar
• Vasudevan J, Johnson AT, Huang D, et al. Inventors. Compounds having activity as inhibitors of cytochrome P450RAI. US6369225; 2002
   Google Scholar
• Njar VC, Brodie AM, Nnane IP; Inventors. C-4 substituted retinoids. US7265143; 2007
   Google Scholar
• Johnson AT, Chandraratna RA. Novel retinoids with receptor selectivity and functional selectivity. Br J Dermatol 1999;140:12-17
   PubMedGoogle Scholar
• Standeven AM, Johnson AT, Escobar M, et al. Specific Antagonist of Retinoid Toxicity in Mice. Toxicol Appl Pharmacol 1996;138:169-75
   PubMedGoogle Scholar
• Patel JB, Mehta J, Belosay A, et al. Novel retinoic acid metabolism blocking agents have potent inhibitory activities on human breast cancer cells and tumour growth. Br J Cancer 2007;96:1204-15
   PubMed Web of Science ®Google Scholar
• Mccaffery P, Simons C. Prospective teratology of retinoic acid metabolic blocking agents (RAMBAs) and loss of CYP26 activity. Curr Pharm Des 2007;13:3020-37
   PubMed Web of Science ®Google Scholar
• Denis L, Debruyne F, De Porre P, et al. Early clinical experience with liarozole (Liazal™) in patients with progressive prostate cancer. Eur J Cancer 1998;34:469-75
   PubMed Web of Science ®Google Scholar
• Shin’ichi Shimada S-G, Shin Nomoto K-G, Masayuki Okue S-G, et al. Inventors. Benzofuran derivatives. US6689798; 2004
   Google Scholar
• Janssen MAC, Raeymaekers AHM, Freyne EJE, et al. Inventors. Pyrroloimidazolyl and imidazopyridinyl substituted 1H-benzimidazole derivatives. US5491161; 1996
   Google Scholar
• Tasaka A, Hitaka T, Matsunaga N, et al. Inventors. Imidazole derivatives, production method thereof and use thereof. US7141598; 2006
   Google Scholar
• Tasaka A, Matsunaga N, Ojida A, et al. Inventors. Imidazole derivatives, process for their preparation and their use. US6960586; 2005
   Google Scholar
• Bock MG, Gaul C, Gummadi V, et al. Inventors. Inhibitors of CYP 17. US8263635; 2012
   Google Scholar
• Brodie A, Njar V; Inventors. 17-Azolyl steroids useful as androgren synthesis inhibitors. US6200965; 2001
   Google Scholar
• Handratta VD, Jelovac D, Long BJ, et al. Potent CYP17 inhibitors: improved syntheses, pharmacokinetics and anti-tumor activity in the LNCaP human prostate cancer model. J Steroid Biochem Mol Biol 2004;92:155-65
   PubMedGoogle Scholar
• Brodie A, Njar V; Inventors. C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens, in vitro biological activities, pharmacokinetics and antitumor activity. US7875599; 2011
   Google Scholar
• Vasaitis T, Belosay A, Schayowitz A, et al. Androgen receptor inactivation contributes to antitumor efficacy of CYP17 inhibitor VN/124-1 in prostate cancer. Mol Cancer Ther 2008;7:2348
   PubMed Web of Science ®Google Scholar
• Vasaitis TS, Bruno RD, Njar VC. CYP17 inhibitors for prostate cancer therapy. J Steroid Biochem Mol Biol 2011;125:23-31
   PubMed Web of Science ®Google Scholar
• Barrie SE, Hardcastle IR, Jarman M, et al. Inventors. Method for preparing 17-substituted steroids useful in cancer treatment. US5618807; 1997
   Google Scholar
• Jordan VC, Brodie AMH. Development and evolution of therapies targeted to the estrogen receptor for the treatment and prevention of breast cancer. Steroids 2007;72:7-25
   PubMed Web of Science ®Google Scholar
• Brodie A, Njar V, Macedo LF, et al. The Coffey Lecture: steroidogenic enzyme inhibitors and hormone dependent cancer. Urol Oncol 2009;27:53-63
   PubMedGoogle Scholar
• Thompson EA, Siiteri PK. Utilization of oxygen and reduced ricotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione. J Biol Chem 1974;249:5364-72
   PubMed Web of Science ®Google Scholar
• Tsuneo Kanamaru T, Tsuneaki Hida O, Masayuki Muroi S; Inventors. Physiologically active substance TAN-931, its derivatives, their production and use. US5196564; 1993
   Google Scholar
• Ishii T, Hida T, Ishimaru T, et al. Tan-931 a novel nonsteroidal aromatase inhibitor produced by Penicillium funiculosum No. 8974. I, Taxonomy, fermentation, isolation, characterization and biological activities. J Antibiot (Tokyo) 1991;44:589-99
   PubMedGoogle Scholar
• Bowman RM, Steele RE, Browne LJ; Inventors. Alpha-heterocycle substituted tolunitriles. EP0236940 B1; 1993
   Google Scholar
• Bowman RM, Steele RE, Browne LJ; Inventors. Alpha-heterocycle substituted tolunitriles. US5071861; 1991
   Google Scholar
• Differding E, Lang M, Stanek J; Inventors. 4-[α(cyanophenyl)-1-(1,2,3-triazolyl)methyl]-benzonitrile. US5457209; 1995
   Google Scholar
• Karjalainen AJ, Sodervall M-L, Kalapudas AM, et al. Inventors. Selective aromatase inhibiting compounds. US5703109; 1997
   Google Scholar
• Okada M, Kawaminami E, Yoden T, et al. Inventors. Triazolylated tertiary amine compound or salt thereof. US5674886; 1997
   Google Scholar
• Woo LWL, Sutcliffe OB, Bubert C, et al. First dual aromatase-steroid sulfatase inhibitors. J Med Chem 2003;46:3193-6
   PubMed Web of Science ®Google Scholar
• Gourvest J-F, Lesuisse D; Inventors. 10-thioethyl-steroids. US5202314; 1993
   Google Scholar
• Peet NP, Burkhart JP, Johnston JON; Inventors. Haloethyl-substituted steroid enzyme inhibitors. US5252565; 1993
   Google Scholar
• Burkhart JP, Peet NP, Johnston JON; Inventors. Haloethyl-substituted steroidal enzyme inhibitors. EP 0450515 B1; 1995
   Google Scholar
• Koizumi N, Takegawa S, Iwashita S, et al. Inventors. 7-substituted oxa- or azasteroid compound. US5539127; 1996
   Google Scholar
• Koizumi N, Takegawa S, Iwashita S, et al. Inventors. Oxa- or azasteroid derivatives. US5519051; 1996
   Google Scholar
• Koizumi N, Takegawa S, Iwashita ST, et al. Inventors. 7-Substituted oxasteroid compound. EP 0663402 B1; 1999
   Google Scholar
• Koizumi N, Takegawa S, Iwashita S, et al. Inventors. -New D-homo-17-oxa and D-homo-17-aza-androstane derivatives. EP0582713 B1; 1997
   Google Scholar
• Abul-Hajj YJ, Akanni A; Inventors. 6-alkynyl steroids. US5866558; 1999
   Google Scholar
• Reed MJ, Potter BVL; Inventors. Steroid sulphatase inhibitors. US6903084; 2005
   Google Scholar
• Rodrigues AD. Drug-drug interactions. CRC Press, London; 2013
   Google Scholar
• Francis S, Shields M, Jacobs H, Delgoda R. In-vitro assessment of chromones, alkaloids and other natural products from Caribbean plants as potential anti-tuberculars and chemopreventors. In: Natural products: structure, bioactivity and applications. Nova Publishers, New York; 2012
   Google Scholar
• Hu OY-P, Hsiong C-H, Kuo BP-C, et al. Inventors. Cytochrome P450 3A inhibitors and enhancers. US7169763; 2007
   Google Scholar
• Ren K, Lu X, Luo X; Inventors. Inhibition of CYP450 1A2, 2A6, 2C9, 2C19, 2D6, 2E1, and 3A4 in cryopreserved human hepatocytes by a Tripterygium Wilfordii Hook. F. extract. US7097865; 2006
   Google Scholar
• Badal S, Williams SA, Huang G, et al. Cytochrome P450 1 enzyme inhibition and anticancer potential of chromene amides from Amyris plumieri. Fitoterapia 2011;82:230-6
   PubMedGoogle Scholar
• Badal S, Delgoda R. Role of the modulation of CYP1A1 expression and activity in chemoprevention. J Appl Toxicol 2014; published online 14 February 2014; doi: 10.1002/jat.2968
   PubMedGoogle Scholar
• He K, Hollenberg PF, Woolf TF; Inventors. Compositions containing Bergamottin for increasing the oral bioavailability of pharmaceutical agents. US6509371; 2003
   Google Scholar
• Edwards DJ, Woster PM; Inventors. 6’,7’-dihydroxybergamottin, a cytochrome P450 inhibitor in grapefruit. US6160006 A; 2000
   Google Scholar
• Planken SP, Sutton SC, Chen R; Inventors. Therapeutic compounds. US7919488; 2011
   Google Scholar
• Kempf DJ; Inventor. Compounds that are useful for improving pharmacokinetics. US8133892; 2012
   Google Scholar
• Norbeck D, Kempf DJT, Leonard JM, et al. Inventors. Method for improving pharmacokinetics. US6037157; 2000
   Google Scholar
• Norbeck D, Kempf DJT, Leonard JM, et al. Inventors. Method for improving pharmacokinetics. US6703403; 2004
   Google Scholar
• Norbeck D, Kempf DJT, Leonard JM, et al. Inventors. Use of ritonavir (abt-538) for improving the pharmacokinetics of drugs metabolized by cytochrome P450 in a method of treating AIDS. EP0871465 B1; 2002
   Google Scholar
• Woolf TF; Inventor. Nitrogen substituted acridine and cytochrome P450 inhibitors and methods of use. US5422350; 1995
   Google Scholar
• Smith RA; Inventor. Use of a cytochrome oxidase inhibitor to increase the cough-suppressing activity of dextromorphan. US5350756; 1994
   Google Scholar
• Walker KAM, Burton PM, Swinney DC; Inventors. 1,3-Dioxolane derivatives as cholesterol-lowering agents. EP0492474 B1; 1997
   Google Scholar
• Zarn JA, Bruschweiler BJ, Schlatter JR. Azole fungicides affect mammalian steroidogenesis by inhibiting sterol 14 alpha-demethylase and aromatase. Environ Health Perspect 2003;111:255-61
   PubMed Web of Science ®Google Scholar
• Treuner UD; Inventor. Aminoalkylphosphonic acid esters of natural 4-methoxy-5-methyl-pyran-3-ol and derivatives thereof. US5248790; 1993
   Google Scholar
• Kirsch DR, O’sullivan J, Phillipson DW; Inventors. Scopularin. US5294725; 1994
   Google Scholar
• Isin EM, Guengerich FP. Complex reactions catalyzed by cytochrome P450 enzymes. Biochim Biophys Acta 2007;1770:314-29
   PubMed Web of Science ®Google Scholar
• Delgoda R, Westlake ACG. Herbal interactions involving cytochrome P450 enzymes: a mini review. Toxicol Rev 2004;23:239-49
   PubMedGoogle Scholar
• Lamb DC, Waterman MR, Kelly SL, et al. Cytochromes P450 and drug discovery. Curr Opin Biotechnol 2007;18:504-12
   PubMed Web of Science ®Google Scholar
• Buzzetti F, Barbugian N, Lombardi P, et al. Inventors. 6-substituted androsta-1,4-diene-3,17-diones. US4808616; 1989
   Google Scholar
• Chow H-HS, Garland LL, Hsu C-H, et al. Resveratrol modulates drug- and carcinogen-metabolizing enzymes in a healthy volunteer study. Cancer Prev Res (Phila) 2010;3:1168-75
   PubMed Web of Science ®Google Scholar
• Anwar-Mohamed A, Zordoky BN, Aboutabl ME, et al. Alteration of cardiac cytochrome P450-mediated arachidonic acid metabolism in response to lipopolysaccharide-induced acute systemic inflammation. Pharmacol Res 2010;61:410-18
   PubMed Web of Science ®Google Scholar
• Mookherjee S, Acharya M, Banerjee D, et al. Molecular basis for involvement of CYP1B1 in MYOC upregulation and its potential implication in glaucoma pathogenesis. PLoS One 2012;7:e45077
   Google Scholar
• Potter GA, Patterson LH, Burke MD; Inventors. Hydroxylation activated prodrugs. US6214886; 2001
   Google Scholar
• Potter GA, Patterson LH, Burke MD; Inventors. Hydroxylation activated drug release. US20020037296 A1; 2002
   Google Scholar
• Janssen MAC, Raeymaekers AHM, Freyne EJE, et al. Inventors. Pyrroloimidazolyl and imidazopyridinyl substituted 1h-benzimidazole derivatives as aromatase inhibitors. EP0625155 B1; 2001
   Google Scholar
• Kaku T, Hitaka T, Ojida A, et al. Discovery of orteronel (TAK-700), a naphthylmethylimidazole derivative, as a highly selective 17,20-lyase inhibitor with potential utility in the treatment of prostate cancer. Bioorg Med Chem 2011;19:6383-99
   PubMed Web of Science ®Google Scholar