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Tanomastat

Names

[ CAS No. ]:
179545-77-8

[ Name ]:
Tanomastat

[Synonym ]:
BAY12-9566,(S)-4Chloro-g-oxo-a-[(phenylthio)methyl][1,1biphenyl]-4-butanoicAcid
(S)-4-[4-(4-Chlorophenyl)phenyl]-4-oxo-2-(phenylsulfanylmethyl)butanoic acid
(S)-4'-Chloro-g-oxo-a-[(phenylthio)methyl][1,1'-biphenyl]-4-butanoic acid

Biological Activity

[Description]:

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].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

[Target]

MMP-2:11 nM (Ki)

MMP-3:143 nM (Ki)

MMP-9:301 nM (Ki)

MMP-13:1470 nM (Ki)


[In Vitro]

Tanomastat (BAY 12-9566) (1-10000 nM; 6 hours) prevents matrix invasion by endothelial cells in a concentration-dependent manner (IC50=840 nM), without affecting cell proliferation[2]. Tanomastat (BAY 12-9566) (1-00 µM; 5 days) inhibits tubule formation completely at 15-100 µM[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.

[References]

[1]. Leung D, et al. Protease inhibitors: current status and future prospects. J Med Chem. 2000 Feb 10;43(3):305-41.

[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.

[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.

Chemical & Physical Properties

[ Density]:
1.33g/cm3

[ Boiling Point ]:
620.1ºC at 760 mmHg

[ Melting Point ]:
110-110.5ºC

[ Molecular Formula ]:
C23H19ClO3S

[ Molecular Weight ]:
410.91300

[ Flash Point ]:
328.8ºC

[ Exact Mass ]:
410.07400

[ PSA ]:
79.67000

[ LogP ]:
6.07290

[ Vapour Pressure ]:
3.07E-16mmHg at 25°C

[ Index of Refraction ]:
1.662

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds