Chemistry:Batimastat

Short description: Chemical compound

Batimastat

Clinical data
Pregnancy category	N/A
Routes of administration	Injection into pleural space or abdomen
ATC code	none
Legal status
Legal status	Never marketed
Identifiers
IUPAC name (2R,3S)-N4-Hydroxy-2-isobutyl-N1-[(2S)-1-(methylamino)-1-oxo-3-phenyl-2-propanyl]-3-[(2-thienylsulfanyl)methyl]succinamide
CAS Number	130370-60-4
PubChem CID	5362422
IUPHAR/BPS	5145
DrugBank	DB03880
ChemSpider	4515033
UNII	BK349F52C9
KEGG	D03061
ChEBI	CHEBI:195398
ChEMBL	ChEMBL279786
Chemical and physical data
Formula	C23H31N3O4S2
Molar mass	477.64 g·mol−1
3D model (JSmol)	Interactive image
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 (mnemonic: batty-mustard) (INN/USAN, codenamed BB-94) is a drug that was invented by Laurie Hines of British Biotech (now Vernalis). It is an antimetastatic drug that belongs to the family of drugs called angiogenesis inhibitors. It acts as a matrix metalloproteinase inhibitor (MMPI) by mimicking natural MMPI peptides. Dan Lednicer wrote about this compound in book #6 of his organic drug synthesis series.

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.

It is well-known that other methods of administration include transdermal (skin lotion) as well as rectal suppositories.

References

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