ChemicalBook > CAS DataBase List > Batimastat

Batimastat

Product Name
Batimastat
CAS No.
130370-60-4
Chemical Name
Batimastat
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)-;(2S,3R)-N1-Hydroxy-3-isobutyl-N4-((S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl)-2-((thiophen-2-ylthio)methyl)succinamide;(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
CBNumber
CB1874927
Molecular Formula
C23H31N3O4S2
Formula Weight
477.64
MOL File
130370-60-4.mol
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Batimastat Property

Melting point:
236-238°
Density 
1.25±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: ≥15mg/mL
pka
9.04±0.40(Predicted)
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
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Safety

WGK Germany 
3
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0041
Product name
Batimastat
Purity
≥98% (HPLC)
Packaging
5mg
Price
$227
Updated
2024/03/01
Sigma-Aldrich
Product number
5.08408
Product name
InSolution Batimastat - CAS 130370-60-4 - Calbiochem
Packaging
2mg
Price
$132
Updated
2024/03/01
Sigma-Aldrich
Product number
196440
Product name
Batimastat
Packaging
5mg
Price
$272
Updated
2024/03/01
Cayman Chemical
Product number
14742
Product name
Batimastat
Purity
≥98%
Packaging
1mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
14742
Product name
Batimastat
Purity
≥98%
Packaging
5mg
Price
$166
Updated
2024/03/01
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Batimastat Chemical Properties,Usage,Production

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.

Uses

Batimastat has been used to inhibit matrix metalloproteinases (MMPs) activity in various studies.

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 -20°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

Batimastat Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Batimastat manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Batimastat 130370-60-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Batimastat 130370-60-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09

130370-60-4, BatimastatRelated Search:

3,4'-DIAMINODIPHENYLMETHANE Diisobutylaluminium hydride Diisobutylcarbinol CHLOROPHOSPHONAZO III Tivozanib PF-562271 PP2 Ilomastat Ruxolitinib Olaparib 4-Methyl-2-pentanone TRIS EDTA ACETATE BUFFER, 10X, DNASE, RNASE AND PROTEASE FREE, PH 8.3, FOR MOLECULAR BIOLOGY HEXANOHYDROXAMIC ACID ISOBUTYROHYDROXAMIC ACID Batimastat 2-(2-(Methylthio)ethyl)pentanamide

  • Butanediamide, N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)-
  • BB 94
  • (2S,3R)-N-Hydroxy-N'-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide
  • Batimastat
  • (2R,3S)-N4-Hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]butanediamide
  • BatiMastat (MMP Inhibitor)
  • N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)-
  • (2S,3R)-N-Hydroxy-N'-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide Batimastat
  • Batimastat (2S,3R)-N-Hydroxy-N'-[(2S)-1-methylamino-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide
  • Batimastat - CAS 130370-60-4 - Calbiochem
  • InSolution Batimastat - CAS 130370-60-4 - Calbiochem
  • BB94;BB 94
  • (2S,3R)-N1-Hydroxy-3-isobutyl-N4-((S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl)-2-((thiophen-2-ylthio)methyl)succinamide
  • 130370-60-4
  • Inhibitors
  • ProteaseInhibitors