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
  • (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
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.222.897
Chemical and physical data
FormulaC23H31N3O4S2
Molar mass477.64 g·mol−1
3D model (JSmol)
  • O=C(NC)[C@@H](NC(=O)[C@@H]([C@@H](C(=O)NO)CSc1sccc1)CC(C)C)Cc2ccccc2
  • 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.

Public Domain 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.