Batimastat

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 (mnemonic: batty-mustard) (INN/USAN, codenamed BB-94) is a drug that was invented by Colin Campion et al. 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.[1]

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

References

Rothenberg ML, Nelson AR, Hande KR (1999). "New drugs on the horizon: matrix metalloproteinase inhibitors". Stem Cells. 17 (4): 237–40. 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".

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[1] Rothenberg ML, Nelson AR, Hande KR (1999). "New drugs on the horizon: matrix metalloproteinase inhibitors". Stem Cells. 17 (4): 237–40. doi:10.1002/stem.170237. PMID 10437989.