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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.222.897
Chemical and physical data
FormulaC23H31N3O4S2
Molar mass477.64 g·mol−1
3D model (JSmol)
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.

References
  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.

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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.