WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200442
CAS#: 130370-60-4 (free base)
Description: Batimastat (also known as BB-94) is a synthetic matrix metalloproteinase inhibitor that has shown antineoplastic and antiangiogenic activity in various tumor models. Matrix metalloproteinases (MMPs) are thought to play a significant role in tumor invasion and metastasis as well as angiogenesis. Batimastat, also known as BB-94, acts as an inhibitor of metalloproteinase activity by binding the zinc ion in the active site of MMPs.
MedKoo Cat#: 200442
CAS#: 130370-60-4 (free base)
Chemical Formula: C23H31N3O4S2
Exact Mass: 477.1756
Molecular Weight: 477.64
Elemental Analysis: C, 57.84; H, 6.54; N, 8.80; O, 13.40; S, 13.43
Related CAS #: 130370-60-4 (free base) 130464-84-5(sodium)
Synonym: BB94; BB-94; BB 94; Batimastat.
IUPAC/Chemical Name: (2S,3R)-N-Hydroxy-N'-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide.
InChi Key: XFILPEOLDIKJHX-QYZOEREBSA-N
InChi Code: 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
SMILES Code: O=C(NO)[C@@H](CSC1=CC=CS1)[C@@H](CC(C)C)C(N[C@@H](CC2=CC=CC=C2)C(NC)=O)=O
130370-60-4 (Batimastat free base form)
130464-84-5(Batimastat sodium salt form).
Batimastat is a potent, broad spectrum matrix metalloprotease (MMP) inhibitor (IC50 values are 3, 4, 4, 6 and 20 nM for MMP -1, -2, -9, -7 and -3 respectively). Exhibits antiproliferative, anti-invasive and antimetastatic activity in human ovarian carcinoma xenografts in vivo .
Batimastat (INN/USAN, codenamed BB-94) is an anticancer drug that belongs to the family of drugs called angiogenesis inhibitors. It acts as a matrix metalloproteinase inhibitor (MMPI) by mimicking natural MMPI peptides. 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. (http://en.wikipedia.org/wiki/Batimastat)
1: Xiao L, Wang M. Batimastat Nanoparticles Associated with Transcatheter Arterial Chemoembolization Decrease Hepatocellular Carcinoma Recurrence. Cell Biochem Biophys. 2014 Mar 18. [Epub ahead of print] PubMed PMID: 24639109.
2: Hall T, Shieh HS, Day JE, Caspers N, Chrencik JE, Williams JM, Pegg LE, Pauley AM, Moon AF, Krahn JM, Fischer DH, Kiefer JR, Tomasselli AG, Zack MD. Structure of human ADAM-8 catalytic domain complexed with batimastat. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2012 Jun 1;68(Pt 6):616-21. doi: 10.1107/S1744309112015618. Epub 2012 May 22. PubMed PMID: 22684055; PubMed Central PMCID: PMC3370895.
3: Kumar A, Bhatnagar S, Kumar A. Matrix metalloproteinase inhibitor batimastat alleviates pathology and improves skeletal muscle function in dystrophin-deficient mdx mice. Am J Pathol. 2010 Jul;177(1):248-60. doi: 10.2353/ajpath.2010.091176. Epub 2010 May 14. PubMed PMID: 20472898; PubMed Central PMCID: PMC2893668.
4: Ge SL, Gong WH, Zhang CX, Zhang L, Han PH, Zhang SQ, Feng JB, Zhou DC. [Protective role of MMP-9 inhibitor batimastat in acute lung injury after cardiopulmonary bypass]. Zhonghua Wai Ke Za Zhi. 2010 Jan 1;48(1):57-61. Chinese. PubMed PMID: 20302758.
5: Mucha SA, Meleń-Mucha G, Godlewski A, Stepień H. Inhibition of estrogen-induced pituitary tumor growth and angiogenesis in Fischer 344 rats by the matrix metalloproteinase inhibitor batimastat. Virchows Arch. 2007 Mar;450(3):335-41. Epub 2007 Jan 18. PubMed PMID: 17235567.
6: Araujo CM, Rando GA, Mauro MF, CristÃ³vÃ£o SA, Sanchez IS, Salman AA, Oliveira Neto JB, Mangione JA. [Batimastat-eluting stent implantation for the treatment of coronary artery disease: results of the Brazilian pilot study]. Arq Bras Cardiol. 2005 Mar;84(3):256-60. Epub 2005 Apr 15. Portuguese. PubMed PMID: 15868002.
7: van Beusekom HM, Post MJ, Whelan DM, de Smet BJ, Duncker DJ, van der Giessen WJ. Metalloproteinase inhibition by batimastat does not reduce neointimal thickening in stented atherosclerotic porcine femoral arteries. Cardiovasc Radiat Med. 2003 Oct-Dec;4(4):186-91. PubMed PMID: 15321056.
8: BjÃ¶rnsson MJ, Havemose-Poulsen A, Stoltze K, Holmstrup P. Influence of the matrix metalloproteinase inhibitor batimastat (BB-94) on periodontal bone destruction in Sprague-Dawley rats. J Periodontal Res. 2004 Aug;39(4):269-74. PubMed PMID: 15206921.
9: Rucavado A, Escalante T, GutiÃ©rrez JM. Effect of the metalloproteinase inhibitor batimastat in the systemic toxicity induced by Bothrops asper snake venom: understanding the role of metalloproteinases in envenomation. Toxicon. 2004 Mar 15;43(4):417-24. PubMed PMID: 15051405.
10: Santucci MB, Ciaramella A, Mattei M, Sumerska T, Fraziano M. Batimastat reduces Mycobacterium tuberculosis-induced apoptosis in macrophages. Int Immunopharmacol. 2003 Nov;3(12):1657-65. PubMed PMID: 14555290.