Antidotal efficacies of the cyanide antidote candidate dimethyl trisulfide alone and in combination with cobinamide derivatives

References

• Block E. 1985. The chemistry of garlic and onions. Sci Am. 252:94–99.
   Web of Science ®Google Scholar
• Borron SW, Stonerook M, Reid F. 2006. Efficacy of hydroxocobalamin for treatment of acute cyanide poisoning in adult beagle dogs. Clin Toxicol. 44:5–15.
   PubMed Web of Science ®Google Scholar
• Broderick KE, Singh V, Zhuang S, Kambo A, Chen JC, Sharma VS, Pilz RB, Gerry R, Boss GR. 2005. Nitric oxide scavenging by the cobalamin precursor cobinamide. J Biol Chem. 280:8678–8685.
   PubMed Web of Science ®Google Scholar
• Bruce RD. 1985. An up-and-down procedure for acute toxicity testing. Fundam Appl Toxicol. 5:151–157.
   PubMedGoogle Scholar
• Chan A, Balasubramanian M, Blackledge W, Mohammad OM, Alvarez L, Boss GR, Bigby TD. 2010. Cobinamide is superior to other treatments in a mouse model of cyanide poisoning. Clin Toxicol (Phila). 48:709–717.
   PubMed Web of Science ®Google Scholar
• Chan A, Jiang J, Fridman A, Guo LT, Shelton GD, Liu M-T, Green C, Haushalter KJ, Patel HH, Lee J, et al. 2015. Nitrocobinamide, a new cyanide antidote that can be administered by intramuscular injection. J Med Chem. 58:1750–1759.
   PubMed Web of Science ®Google Scholar
• Chen KK, Rose CL. 1952. Nitrite and thiosulfate therapy in cyanide poisoning. J Am Med Assoc. 149:113–119.
   PubMed Web of Science ®Google Scholar
• Cronican AA, Frawley KL, Straw EP, Lopez-Manzano E, Praekunatham H, Peterson J, Pearce LL. 2018. A comparison of the cyanide-scavenging capabilities of some cobalt-containing complexes in mice. Chem Res Toxicol. 31:259–268.
   PubMed Web of Science ®Google Scholar
• De Silva D, Lee S, Duke A, Angalakurthi S, Chou CE, Ebrahimpour A, Thompson DE, Petrikovics I. 2016. Intravascular residence time determination for the cyanide antidote dimethyl trisulfide in rat by using liquid-liquid extraction coupled with high performance liquid chromatography. J Anal Methods Chem. 6546475:1–6.
   Google Scholar
• DeLeon SM, Downey JD, Hildenberger DM, Rhoomes MO, Booker L, Rockwood GA, Basi KA. 2018. DMTS is an effective treatment in both inhalation and injection models for cyanide poisoning using unanesthetized mice. Clin Toxicol. 56:332–341.
   PubMed Web of Science ®Google Scholar
• Dixon WJ, Massey FJ. 1983. Introduction to statistical analysis. Frederick (MD): McGraw-Hill Inc.; p. 434–438.
   Google Scholar
• Dixon WJ. 1965. The up-and-down method for small animal samples. J Am Stat Assoc. 60:967–978.
   Web of Science ®Google Scholar
• Dong X, Kiss L, Petrikovics I, Thompson DE. 2017. Reaction of dimethyl trisulfide with hemoglobin. Chem Res Toxicol. 30:1661–1663.
   PubMed Web of Science ®Google Scholar
• Efron B. 1979. Bootstrap methods: another look at the jackknife. Ann Statist. 7:1–26.
   Web of Science ®Google Scholar
• Kanai AJ, Pearce LL, Clemens PR, Birder LA, VanBibber MM, Choi S-Y, de Groat WC, Peterson J. 2001. Identification of a neuronal nitric oxide synthase in isolated cardiac mitochondria using electrochemical detection. Proc Natl Acad Sci USA. 98:14126–14131.
   PubMed Web of Science ®Google Scholar
• Kiss L, Bocsik A, Walter FR, Ross J, Brown D, Mendenhall BA, Crews SR, Lowry J, Coronado V, Thompson DE, et al. 2017. In vitro and in vivo blood–brain barrier penetration studies with the novel cyanide antidote candidate dimethyl trisulfide in mice. Toxicol Sci. 160:398–407.
   PubMed Web of Science ®Google Scholar
• Kovacs K, Duke AC, Shifflet M, Winner B, Lee SA, Rockwood GA, Petrikovics I. 2016a. Parenteral dosage form development and testing of dimethyl trisulfide, as an antidote candidate to combat cyanide intoxication. Pharm Dev Technol. 7450:1–6.
   Google Scholar
• Kovacs K, Jayanna PK, Duke A, Winner B, Negrito M, Angalakurthi S, Yu JC, Füredi P, Ludányi K, Sipos P, et al. 2016b. A lipid base formulation for intramuscular administration of a novel sulfur donor for cyanide antagonism. CDD. 13:1351–1357.
   PubMed Web of Science ®Google Scholar
• Lee J, Mahon SB, Mukai D, Burney T, Katebian BS, Chan A, Bebarta VS, Yoon D, Boss G, Brenner M. 2016. The vitamin B12 analog cobinamide is an effective antidote for oral cyanide poisoning. J Med Toxicol. 12:370–379.
   PubMed Web of Science ®Google Scholar
• Litchfield JT, Wilcoxon F. 1949. A simplified method of evaluating dose-effect experiments. J Pharmacol Exp Ther. 96:99–113.
   PubMed Web of Science ®Google Scholar
• Marraffa JM, Cohen V, Howland MA. 2012. Antidotes for toxicological emergencies: a practical review. Am J Health Syst Pharm. 69:199–212.
   PubMed Web of Science ®Google Scholar
• National Research Council. 2010. Guide for the care and use of laboratory animals. Washington, DC: National Academies Press.
   Google Scholar
• Pearce LL, Bominaar EL, Hill BC, Peterson J. 2003. Reversal of cyanide inhibition of cytochrome c oxidase by the auxiliary substrate nitric oxide: an endogenous antidote to cyanide poisoning. J Biol Chem. 278:52139–52145.
   PubMed Web of Science ®Google Scholar
• Petrikovics I, McGuinn WD, Cannon EP, Pei L, Way JL. 1994. Encapsulation of rhodanese and organic thiosulfonates by mouse erythrocytes. Toxicol Sci. 23:70–75.
   Google Scholar
• Rockwood GA, Thompson DE, Petrikovics I. 2016. Dimethyl trisulfide: a novel cyanide countermeasure. Toxicol Ind Health. 32:2009–2016.
   PubMed Web of Science ®Google Scholar
• Sherman C, Smith CM, Wirtz KR, Schulze E, inventors; Hope Medical Enterprises, Inc., assignee. 2013 Jul 30. Sodium thiosulfate-containing pharmaceutical compositions. United States patent US 8.496,973 B2.
   Google Scholar
• Sherman C, Lepine AJ, Smith CM, Wirtz KR, Schulze E, inventors; Hope Medical Enterprises, Inc., assignee. 2013 Oct 29. Sodium nitrite-containing pharmaceutical compositions. United States patent US 8,568,793 B2.
   Google Scholar
• Sherman C, Smith CM, Wirtz KR, Schulze E, inventors; Hope Medical Enterprises, Inc., assignee. 2016 May 24. Sodium thiosulfate-containing pharmaceutical compositions. United States patent US 9,345,724 B2.
   Google Scholar
• Sherman C, Smith CM, Wirtz KR, Schulze E, inventors; Hope Medical Enterprises, Inc., assignee. 2017 Mar 7. Sodium thiosulfate-containing pharmaceutical compositions. United States patent US 9,585,912 B2.
   Google Scholar
• Schulz V. 1984. Clinical pharmacokinetics of nitroprusside, cyanide, thiosulphate and thiocyanate. Clin Pharmacokinet. 9:239–251.
   PubMed Web of Science ®Google Scholar
• Vogel SN, Sultan TR, Ten Eyck RP. 1981. Cyanide poisoning. Clin Toxicol. 18:367–383.
   PubMed Web of Science ®Google Scholar
• Way JL, Leung P, Cannon E, Morgan R, Tamulinas C, Leong-Way J, Baxter L, Nagi A, Chui C. 1988. The mechanism of cyanide intoxication and its antagonism. Ciba Found Symp. 140:232–243.
   PubMedGoogle Scholar
• Zakharov S, Vaneckova M, Seidl Z, Diblik P, Kuthan P, Urban P, Navratil T, Pelclova D. 2015. Successful use of hydroxocobalamin and sodium thiosulfate in acute cyanide poisoning: a case report with follow-up. Basic Clin Pharmacol Toxicol. 117:209–212.
   PubMed Web of Science ®Google Scholar