| Identification | Back Directory | [Name]
4-{4'-chloro-[1,1'-biphenyl]-4-yl}-4-oxo-2-[(phenylsulfanyl)methyl]butanoic acid | [CAS]
179545-76-7 | [Synonyms]
(Rac)-Tanomastat
[1,1'-Biphenyl]-4-butanoic acid, 4'-chloro-γ-oxo-α-[(phenylthio)methyl]-
4-{4'-chloro-[1,1'-biphenyl]-4-yl}-4-oxo-2-[(phenylsulfanyl)methyl]butanoic acid | [Molecular Formula]
C23H19ClO3S | [MDL Number]
MFCD23099769 | [MOL File]
179545-76-7.mol | [Molecular Weight]
410.91 |
| Hazard Information | Back Directory | [Uses]
(Rac)-Tanomastat ((Rac)-BAY 12-9566) is the racemate of Tanomastat. Tanomastat (BAY 12-9566) is an orally bioavailable, non-peptidic biphenyl matrix metalloproteinases (MMPs) inhibitor with a Zn-binding carboxyl group. The Ki values are 11, 143, 301, and 1470 nM for MMP-2, MMP-3, MMP-9, MMP-13 respectively. Tanomastat shows anti-invasive and antimetastatic activity in several experimental tumor models[1][2][3]. | [in vivo]
Tanomastat (BAY 12-9566) (100 mg/kg; p.o.; daily for a 7-week period) inhibits local tumor regrowth without causing any toxic effect, and inhibits the number and volume of lung metastases[3]. | Animal Model: | Six- to eight-week-old female BALB/c nude mice (bearing MDA-MB-435 cells)[3] | | Dosage: | 100 mg/kg | | Administration: | P.o.; daily for a 7-week period | | Result: | Inhibited local tumor regrowth by 58% without causing any toxic effect, and inhibited the number and volume of lung metastases by 57 and 88%, respectively. |
| [IC 50]
MMP-2: 11 nM (Ki); MMP-3: 143 nM (Ki); MMP-9: 301 nM (Ki); MMP-13: 1470 nM (Ki) | [References]
[1] Leung D, et al. Protease inhibitors: current status and future prospects. J Med Chem. 2000 Feb 10;43(3):305-41. DOI:10.1021/jm990412m
[2] Gatto C, et al. BAY 12-9566, a novel inhibitor of matrix metalloproteinases with antiangiogenic activity. Clin Cancer Res. 1999 Nov;5(11):3603-7. PMID:10589777
[3] Nozaki S, et al. Activity of biphenyl matrix metalloproteinase inhibitor BAY 12-9566 in a human breast cancerorthotopic model. Clin Exp Metastasis. 2003;20(5):407-12. DOI:10.1023/a:1025473709656
[4] Harold Clinton Eugene Kluender, et al. Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitiors. WO1996015096A1. |
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Key Organics Ltd.
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+44 (0) 1840-212137 |
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www.keyorganics.net |
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