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MedKoo Cat#: 200442 | Name: Batimastat
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Batimastat
Batimastat
CAS#130370-60-4 (free base)

Theoretical Analysis

MedKoo Cat#: 200442

Name: Batimastat

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

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,350.00 Ready to ship
200mg USD 2,650.00 Ready to ship
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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
Appearance
white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related: 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)    
Biological target:
Batimastat is a broad spectrum MMP inhibitor with IC50 of 3, 4, 4, 6, and 20 nM for MMP-1, MMP-2, MMP-9, MMP-7 and MMP-3, respectively.
In vitro activity:
To further investigate the importance of HER receptors and HER ligand shedding for cell growth and signaling in the resistant cell lines, 164R-7 was treated for five days with gefitinib (preferentially targeting EGFR), CI-1033 (pan-HER inhibitor), or the metalloproteinase inhibitors TAPI-2, BB-94 or GM6001 (Fig. 4A). Compared to growth of the untreated control, 1 μM gefitinib or 0.5 μM CI-1033 significantly inhibited growth of 164R-7 by 30 and 80%, respectively. Moreover, the broad-spectrum metalloproteinase inhibitor BB-94 significantly inhibited resistant growth by 70%, whereas the more selective metalloproteinase inhibitors TAPI-2 and GM6001 had no inhibitory effect on growth of 164R-7 (Fig. 4A). When the five-day dose-response growth experiments with BB-94 were performed, increasing concentrations (0.01–10 μM) of BB-94 resulted in a dose-dependent growth inhibition up to 50% and 80% compared to the untreated control for 164R-7 and 164R-5, respectively, whereas growth of the parental MCF-7 cells in the presence of increasing concentrations of BB-94 was <20% inhibited compared to the untreated control (Fig. 4B). Thus, BB-94 preferentially inhibited growth of fulvestrant-resistant MCF-7 cell lines. Reference: Int J Oncol. 2014 Jul;45(1):393-400. https://www.spandidos-publications.com/ijo/45/1/393
In vivo activity:
Firstly, using SR-based X-ray microangiography, this study found that TE did induce significant microvasculature alterations in hepatic and renal small vessel branches, especially in distal vessels as usual, while BB-94 significantly improved TE-induced hepatic and renal microvasculature changes in DJES mouse model. Secondly, under SR-μCT, TE also caused incomplete hepatic and renal distal vessel branches, while BB-94 reduced TE-induced hepatic and renal microvasculature changes in DJES rat model. In addition, being consistent with imaging results, histopathological and TUNEL-like staining observations also clearly corroborated this hypothesis, as BB-94 was highly effective in neutralizing TE-induced extensive hemorrhage and necrosis in DJES rat model. Taken together with previous findings, present data suggested that TE contained some metalloproteinases, which disrupted the integrity of microvasculars, resulting in liver and kidney hemorrhagic injuries in DJES, while rapid administration of BB-94 was useful in preventing TE-induced microvasculature alterations and appeared to be a promising therapeutic alternative for the treatment of DJES. Reference: Toxicon. 2015 Dec 15;108:232-9. https://pubmed.ncbi.nlm.nih.gov/26546696/
Solvent mg/mL mM
Solubility
DMSO 20.0 41.87
DMF 20.0 41.87
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 477.64 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Kirkegaard T, Yde CW, Kveiborg M, Lykkesfeldt AE. The broad-spectrum metalloproteinase inhibitor BB-94 inhibits growth, HER3 and Erk activation in fulvestrant-resistant breast cancer cell lines. Int J Oncol. 2014 Jul;45(1):393-400. doi: 10.3892/ijo.2014.2434. Epub 2014 May 9. PMID: 24819550. 2. Wu Z, Mulatibieke T, Niu M, Li B, Dai J, Ye X, He Y, Chen C, Wen L, Hu G. Inhibition of Matrix Metalloproteinase with BB-94 Protects against Caerulein-Induced Pancreatitis via Modulating Neutrophil and Macrophage Activation. Gastroenterol Res Pract. 2020 Apr 28;2020:8903610. doi: 10.1155/2020/8903610. PMID: 32411205; PMCID: PMC7204304. 3. Wang B, Liu D, Liu G, Zhang X, Wang Q, Zheng J, Zhou Y, He Q, Zhang L. Protective effects of batimastat against hemorrhagic injuries in delayed jellyfish envenomation syndrome models. Toxicon. 2015 Dec 15;108:232-9. doi: 10.1016/j.toxicon.2015.10.022. Epub 2015 Nov 4. PMID: 26546696.
In vitro protocol:
1. Kirkegaard T, Yde CW, Kveiborg M, Lykkesfeldt AE. The broad-spectrum metalloproteinase inhibitor BB-94 inhibits growth, HER3 and Erk activation in fulvestrant-resistant breast cancer cell lines. Int J Oncol. 2014 Jul;45(1):393-400. doi: 10.3892/ijo.2014.2434. Epub 2014 May 9. PMID: 24819550.
In vivo protocol:
1. Wu Z, Mulatibieke T, Niu M, Li B, Dai J, Ye X, He Y, Chen C, Wen L, Hu G. Inhibition of Matrix Metalloproteinase with BB-94 Protects against Caerulein-Induced Pancreatitis via Modulating Neutrophil and Macrophage Activation. Gastroenterol Res Pract. 2020 Apr 28;2020:8903610. doi: 10.1155/2020/8903610. PMID: 32411205; PMCID: PMC7204304. 2. Wang B, Liu D, Liu G, Zhang X, Wang Q, Zheng J, Zhou Y, He Q, Zhang L. Protective effects of batimastat against hemorrhagic injuries in delayed jellyfish envenomation syndrome models. Toxicon. 2015 Dec 15;108:232-9. doi: 10.1016/j.toxicon.2015.10.022. Epub 2015 Nov 4. PMID: 26546696.
1: Yurtal Z, Ozkan H, Kutlu T, Deveci M, Urfali B, Urfali S. The Matrix Metalloproteinase Inhibitor Batimastat Reduces Epidural Fibrosis After Laminectomy in Rats. Turk Neurosurg. 2023;33(1):162-170. doi: 10.5137/1019-5149.JTN.41841-22.2. PMID: 36482856. 2: Xiao L, Wang M. Batimastat nanoparticles associated with transcatheter arterial chemoembolization decrease hepatocellular carcinoma recurrence. Cell Biochem Biophys. 2014 Sep;70(1):269-72. doi: 10.1007/s12013-014-9893-8. PMID: 24639109. 3: Batimastat. BB 94, collagenase inhibitors-1. Drugs R D. 1999 Feb;1(2):139-41. doi: 10.2165/00126839-199901020-00005. PMID: 10566008. 4: Rasmussen HS, McCann PP. Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat. Pharmacol Ther. 1997;75(1):69-75. doi: 10.1016/s0163-7258(97)00023-5. PMID: 9364582. 5: 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. doi: 10.1016/S1567-5769(03)00202-9. PMID: 14555290. 6: Pollitt CC, Pass MA, Pollitt S. Batimastat (BB-94) inhibits matrix metalloproteinases of equine laminitis. Equine Vet J Suppl. 1998 Sep;(26):119-24. doi: 10.1111/j.2042-3306.1998.tb05130.x. PMID: 9932102. 7: Leriche G, Chen AC, Kim S, Selkoe DJ, Yang J. Fluorescent Analogue of Batimastat Enables Imaging of α-Secretase in Living Cells. ACS Chem Neurosci. 2016 Jan 20;7(1):40-5. doi: 10.1021/acschemneuro.5b00283. Epub 2015 Nov 18. PMID: 26559179; PMCID: PMC4720558. 8: Sledge GW Jr, Qulali M, Goulet R, Bone EA, Fife R. Effect of matrix metalloproteinase inhibitor batimastat on breast cancer regrowth and metastasis in athymic mice. J Natl Cancer Inst. 1995 Oct 18;87(20):1546-50. doi: 10.1093/jnci/87.20.1546. PMID: 7563189. 9: Layfield HJ, Williams HF, Ravishankar D, Mehmi A, Sonavane M, Salim A, Vaiyapuri R, Lakshminarayanan K, Vallance TM, Bicknell AB, Trim SA, Patel K, Vaiyapuri S. Repurposing Cancer Drugs Batimastat and Marimastat to Inhibit the Activity of a Group I Metalloprotease from the Venom of the Western Diamondback Rattlesnake, Crotalus atrox. Toxins (Basel). 2020 May 9;12(5):309. doi: 10.3390/toxins12050309. PMID: 32397419; PMCID: PMC7290494. 10: Caveat investor. Nature. 1998 May 28;393(6683):291. doi: 10.1038/30546. PMID: 9620784. 11: Botos I, Scapozza L, Zhang D, Liotta LA, Meyer EF. Batimastat, a potent matrix mealloproteinase inhibitor, exhibits an unexpected mode of binding. Proc Natl Acad Sci U S A. 1996 Apr 2;93(7):2749-54. doi: 10.1073/pnas.93.7.2749. PMID: 8610113; PMCID: PMC39703. 12: 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. PMID: 20472898; PMCID: PMC2893668. 13: 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. doi: 10.1016/j.carrad.2004.02.004. PMID: 15321056. 14: Araujo CM, Rando GA, Mauro MF, Cristóvão SA, Sanchez IS, Salman AA, Oliveira Neto JB, Mangione JA. Implante de stent eluído com batimastat para o tratamento da doença arterial coronariana: resultados do estudo piloto brasileiro [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. Portuguese. doi: 10.1590/s0066-782x2005000300012. Epub 2005 Apr 15. PMID: 15868002. 15: Wang B, Liu D, Liu G, Zhang X, Wang Q, Zheng J, Zhou Y, He Q, Zhang L. Protective effects of batimastat against hemorrhagic injuries in delayed jellyfish envenomation syndrome models. Toxicon. 2015 Dec 15;108:232-9. doi: 10.1016/j.toxicon.2015.10.022. Epub 2015 Nov 4. PMID: 26546696. 16: 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. PMID: 22684055; PMCID: PMC3370895. 17: Herget J, Novotna J, Bibova J, Povysilova V, Vankova M, Hampl V. Metalloproteinase inhibition by Batimastat attenuates pulmonary hypertension in chronically hypoxic rats. Am J Physiol Lung Cell Mol Physiol. 2003 Jul;285(1):L199-208. doi: 10.1152/ajplung.00167.2002. Epub 2003 Mar 28. PMID: 12665462. 18: Björnsson 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. doi: 10.1111/j.1600-0765.2004.00740.x. PMID: 15206921. 19: Rucavado A, Escalante T, Gutiérrez 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. doi: 10.1016/j.toxicon.2004.01.016. PMID: 15051405. 20: Krüger A, Soeltl R, Sopov I, Kopitz C, Arlt M, Magdolen V, Harbeck N, Gänsbacher B, Schmitt M. Hydroxamate-type matrix metalloproteinase inhibitor batimastat promotes liver metastasis. Cancer Res. 2001 Feb 15;61(4):1272-5. PMID: 11245418.