3-Mercaptopyruvic acid

3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective.[1] Instead, prodrugs, such as sulfanegen, are being evaluated to compensate for the short half-life of 3-mercaptopyruvic acid.[2]

3-Mercaptopyruvic acid

Names
Preferred IUPAC name 2-Oxo-3-sulfanylpropanoic acid
Other names 3-Mercapto-2-oxopropanoic acid 3-MPV 3-MP
Identifiers
CAS Number	2464-23-5^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:16208^Y
ChemSpider	96^Y
IUPHAR/BPS	5118
KEGG	C00957^Y
MeSH	3-mercaptopyruvic+acid
PubChem CID	98
UNII	5Z1F5OW4YB^Y
CompTox Dashboard (EPA)	DTXSID30947575
InChI InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)^Y Key: OJOLFAIGOXZBCI-UHFFFAOYSA-N^Y InChI=1/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6) Key: OJOLFAIGOXZBCI-UHFFFAOYAZ
SMILES C(C(=O)C(=O)O)S O=C(O)C(=O)CS
Properties
Chemical formula	C3H4O3S
Molar mass	120.12 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• 3-mercaptopyruvate sulfurtransferase

References

1. Nagahara, N; Li, Q; Sawada, N (2003). "Do antidotes for acute cyanide poisoning act on mercaptopyruvate sulfurtransferase to facilitate detoxification?". Current Drug Targets. Immune, Endocrine and Metabolic Disorders. 3 (3): 198–204. doi:10.2174/1568008033340162. PMID 12871026.
2. Brenner, M; Kim, JG; Lee, J; Mahon, SB; Lemor, D; Ahdout, R; Boss, GR; Blackledge, W; Jann, L; Nagasawa, HT; Patterson, SE (2010). "Sulfanegen sodium treatment in a rabbit model of sub-lethal cyanide toxicity". Toxicology and Applied Pharmacology. 248 (3): 269–76. doi:10.1016/j.taap.2010.08.002. PMC 3382974. PMID 20705081.