| Identification | Back Directory | [Name]
Batimastat | [CAS]
130370-60-4 | [Synonyms]
BB 94
Batimastat
BB94;BB 94
BatiMastat (MMP Inhibitor)
Batimastat - CAS 130370-60-4 - Calbiochem
InSolution Batimastat - CAS 130370-60-4 - Calbiochem
N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)-
(2R,3S)-N4-Hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]butanediamide
(2S,3R)-N-Hydroxy-N'-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide
Butanediamide, N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)-
Batimastat
(2S,3R)-N-Hydroxy-N'-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide
(2S,3R)-N-Hydroxy-N'-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide Batimastat | [Molecular Formula]
C23H31N3O4S2 | [MDL Number]
MFCD00866533 | [MOL File]
130370-60-4.mol | [Molecular Weight]
477.64 |
| Chemical Properties | Back Directory | [Melting point ]
236-238° | [storage temp. ]
-20°C | [solubility ]
DMSO: ≥15mg/mL | [form ]
powder | [color ]
white to tan | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. | [InChIKey]
XFILPEOLDIKJHX-QYZOEREBSA-N |
| Hazard Information | Back Directory | [Description]
Batimastat (130370-60-4) is a potent, broad spectrum MMP inhibitor (IC50 =3, 4, 4, 6 and 20 nM for MMPs -1, -2, -9, -7 and -3 respectively). Exhibits antiproliferative, anti-invasive and antimetastatic activity in human colon1, ovarian2 and prostate3 xenografts in vivo. Attenuates neuroinflammation following focal cerebral ischemia in mice.4 Inhibits α-secretase.5 Inhibits snake venom (Bothrops asper) lethality.6 | [Originator]
Batimastat,British Biotech | [Uses]
Antineoplastic. | [Therapeutic Function]
Antineoplastic | [General Description]
A Marimastat (Cat. No. 444289) type of peptidyl hydroxamate-based inhibitor that potently inhibits a broad-spectrum of metalloproteinases, including MMP-1, MMP-2, MMP-3/stromelysin, MMP-7/matrilysin, MMP-9, ΔMT1 (MMP-14 without TM domain), ADAM8, and ADAM17/TACE (IC50 = 3, 4, 20, 6, 4, 2.08, 51.3, and 19 nM, respectively), by targeting both the substrate binding site and the active-site Zn2+, while being much less potent toward ACE (Angiotensin Converting Enzyme) or α-secretase (IC50 = 1.6 and 3.3 μM, respectively). Batimastat is widely used in studying the involvement of MMPs in cancinogenesis and non-cancer pathological processes both in cultures in vitro and in animals in vivo. | [Biological Activity]
Potent, broad spectrum matrix metalloprotease (MMP) inhibitor (IC 50 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 . | [Biochem/physiol Actions]
Cell permeable: yes | [Enzyme inhibitor]
This potent, broad-spectrum matrix metalloprotease, or MMP, inhibitor (FW = 477.64 g/mol; CAS 130370-60-4; Solubility: 96 mg/mL DMSO, <1 mg/mL H2O), also known by its code name BB-94 and its systematic name (2R,3S)-N4 -hydroxy-N1 -[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl) ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]butanediamide, targets MMP-1 (IC50 = 3 nM), MMP-2 (IC50 = 4 nM), MMP-9 (IC50 = 4 nM), MMP-7 (IC50 = 6 nM) and MMP-3 (IC50 = 22 nM). Matrix metalloproteinases have been implicated in the growth and spread of metastatic tumors, and Batimastat not only prevents colonization of secondary organs by B16-BL6 cells, but limits the growth of solid tumors. Animals receiving BB-94 (30 mg/kg, i.p., once daily for 60 days, followed by 3 times weekly) show a reduction in the median primary tumor weight from 293 mg in the control group to 144 mg in the treated group. BB-94 treatment also reduces the incidence of local and regional invasion. Batimastat also reduces in vivo growth of experimental hemangiomas, most probably by blocking endothelial cell recruitment by the transformed cells or by interfering with cell organization in vascular structures. Target(s): Trimeresurus mucrosquamatus (Taiwan habu) venom metalloproteinases; matrix metalloproteinases; interstitial collagenase, or MMP1; stromelysin, or MMP3; matrilysin, or MMP7; gelatinase A, or or MMP2; gelatinase B, or or MMP9; neutrophil collagenase, or MMP8; atrolysin C, or Crotalus atrox metalloendopeptidase c; membrane-type 1 matrix metalloproteinase, or MMP14; membrane-type 3 matrix metalloproteinase, or MMP-16; ADAM 17 endopeptidase, or tumor necrosis factor-a converting enzyme; TACE (13- 15); a-secretase; ADAM TS-4 endopeptidase, or aggrecanase; macrophage elastase, or MMP12. | [storage]
Store at 4°C | [References]
1) Wang et al. (1994), Matrix metalloproteinase inhibitor BB-94 (batimastat) inhibits human colon tumor growth and spread in a patient-like orthotopic model in nude mice; Cancer Res., 54 4726
2) Davies et al. (1993), A synthetic matrix metalloproteinase inhibitor decreases tumor burden and prolongs survival of mice bearing human ovarian carcinoma zenografts; Cancer Res., 53 2087
3) Lein et al. (2000), Synthetic inhibitor of matrix metalloproteinase (batimastat) reduces prostate cancer growth in an orthotopic rat model; Prostate, 43 77
4) Park et al. (2011), Matrix metalloproteinase inhibitors attenuate neuroinflammation following focal cerebral ischemia in mice; Korean J. Physiol. Pharmacol., 15 115
5) Dubrovskaya et al. (2006), Effects of an inhibitor of alpha-secretase, which metabolizes the amyloid peptide precursor, on memory formation in rats; Neurosci. Behav. Physiol., 36 911
6) Rucavado et al. (2004), Effects of the metalloproteinase inhibitor batimastat in the systemic toxicity induced by Bothrops asper snake venom: understanding the role of metalloproteinases in envenomation; Toxicon, 43 417 |
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