Batimastat

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

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
ChEMBL	ChEMBL279786
CompTox Dashboard (EPA)	DTXSID20156497
ECHA InfoCard	100.222.897
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 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]

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