Batimastat

Batimastat

Systematic (IUPAC) name
(2R,3S)-N^4-Hydroxy-2-isobutyl-N^1-[(2S)-1-(methylamino)-1-oxo-3-phenyl-2-propanyl]-3-[(2-thienylsulfanyl)methyl]succinamide
Clinical data
Pregnancy category	N/A
Legal status	Never marketed
Routes of administration	Injection into pleural space or abdomen
Identifiers
CAS Number	130370-60-4
ATC code	None
PubChem	CID 5362422
IUPHAR/BPS	5145
DrugBank	DB03880
ChemSpider	4515033
KEGG	D03061
ChEMBL	CHEMBL279786
Chemical data
Formula	C23H31N3O4S2
Molar mass	477.64 g/mol
SMILES O=C(NC)[C@@H](NC(=O)[C@@H]([C@@H](C(=O)NO)CSc1sccc1)CC(C)C)Cc2ccccc2
InChI InChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1 Key:XFILPEOLDIKJHX-QYZOEREBSA-N

Batimastat (INN/USAN, codenamed BB-94) is an anticancer drug that belongs to the family of drugs called angiogenesis inhibitors. It acts as a matrix metalloproteinase inhibitor (MMPI) by mimicking natural MMPI peptides.

Batimastat was the first MMPI that went into clinical trials. First results of a Phase I trial appeared in 1994. The drug reached Phase III but was never marketed; mainly because it couldn't be administered orally (as opposed to the newer and chemically similar MMPI marimastat), and injection into the peritoneum caused peritonitis.^[1]

References

1. Rothenberg, M. L.; Nelson, A. R.; Hande, K. R. (1999). "New Drugs on the Horizon: Matrix Metalloproteinase Inhibitors". Stem Cells 17 (4): 237–240. doi:10.1002/stem.170237. PMID 10437989.

 This article incorporates public domain material from the U.S. National Cancer Institute document "Dictionary of Cancer Terms".