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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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Batimastat Suppliers

China 81 India 1 United Kingdom 2 United States 22 Global 106
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Alabiochem Tech.Co., Ltd.
Tel
0512-58900862 400-0707518
Fax
0086-512-56765862
Email
sales@alabiochem.com
Country
China
ProdList
995
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
meilunui@163.com
Country
China
ProdList
4727
Advantage
58
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.
Tel
025-66099280 17798518460
Fax
(1)02557626880
Email
cfzhang@aikonchem.com
Country
China
ProdList
19915
Advantage
55
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-400-6206333 18521732826
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
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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:

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  • 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