| Identification | Back Directory | [Name]
CP 471,474 | [CAS]
210755-45-6 | [Synonyms]
PF-1626077
CP 471,474
2-(4-(4-Fluorophenoxy)phenylsulfonamido)-N-hydroxy-2-methylpropanamide
2-[[[4-(4-Fluorophenoxy)phenyl]sulfonyl]amino]-N-hydroxy-2-methylpropanamide
Propanamide, 2-[[[4-(4-fluorophenoxy)phenyl]sulfonyl]amino]-N-hydroxy-2-methyl- | [Molecular Formula]
C16H17FN2O5S | [MDL Number]
MFCD16618408 | [MOL File]
210755-45-6.mol | [Molecular Weight]
368.38 |
| Chemical Properties | Back Directory | [Melting point ]
135-137°C (dec.) | [density ]
1.375±0.06 g/cm3(Predicted) | [storage temp. ]
room temp | [solubility ]
DMSO: ≥20mg/mL | [form ]
powder | [pka]
9.33±0.50(Predicted) | [color ]
white to off-white | [InChI]
1S/C16H17FN2O5S/c1-16(2,15(20)18-21)19-25(22,23)14-9-7-13(8-10-14)24-12-5-3-11(17)4-6-12/h3-10,19,21H,1-2H3,(H,18,20) | [InChIKey]
QCOQJYRPDUMCNP-UHFFFAOYSA-N | [SMILES]
CC(C)(NS(=O)(=O)c1ccc(Oc2ccc(F)cc2)cc1)C(=O)NO |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [WGK Germany ]
1 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
CP 471,474 is a broad-spectrum inhibitor of matrix metalloproteinases (MMPs) with IC50 values of 0.7, 16, 13, and 0.9 nM for MMP-2, MMP-3, MMP-9, and MMP-13, respectively. It is selective for these MMPs over MMP-1 (IC50 = 1,170 nM). CP 471,474 reduces left ventricular enlargement and decreases the incidence of cardiac rupture in mouse models of myocardial infarction when administered at doses of 120 mg/kg twice per day and 240 mg/kg per day, respectively. | [Chemical Properties]
White Solid | [Uses]
A broad spectrum inhibitor of matrix metalloproteinases that attenuates early left ventricular dilation after experimental myocardial infarction in mice. Studies show that it also inhibits cigarette smoke-induced lung inflammation and the progression of emphysema in guinea pig models. | [Biochem/physiol Actions]
CP-471474 is a broad spectrum inhibitor of matrix metalloproteinases. CP-471474 has a low nM IC50 efficacy for MMP-2, MMP-3, MMP-9, and MMP-13. CP-471474 has low potency against MMP-1 (IC50 > 1 uM). CP-471474 prevents left ventricular remodeling after experimental myocardial infarction in mice. CP-471474 also inhibits cigarette smoke-induced lung inflammation and the progression of emphysema in guinea pig models. | [in vivo]
CP-471474 plasma levels following subcutaneous injection are 2,020 ng/mL (1 h postdose) to 160 ng/mL (6 h postdose)[2].
CP-471,474 significantly reduces both the extent and severity of inflammation at 2 months. At 4 months, a spontaneous reduction of the inflammatory response is observed in both treated and untreated animals, and consequently no difference is observed between both[2].
CP-471474 significantly decreases the destructive lesions mainly at 2 months and also at 4 months[2].
| Animal Model: | Guinea pigs weighing 400 to 450 g (COPD)[2]. | | Dosage: | 20 mg/kg (also supplemented daily by the diet (200 mg/200 g powdered chow)). | | Administration: | Subcutaneously (in 20% ethanol/80% polyethylene glycol), once a day during the entire course. | | Result: | Lungs derived from smoking animals treated with the compound demonstrated a statistically significant reduction in the destructive lesions.
Showed an increase of both pro–MMP-9 and its active form (lanes 5 to 8) as compared with control animals.
|
| [IC 50]
MMP-2: 0.7 nM (IC50); MMP-13: 0.9 nM (IC50); MMP-9: 13 nM (IC50); MMP-3: 16 nM (IC50); MMP-1: 1170 nM (IC50) | [References]
[1] L E ROHDE. Matrix metalloproteinase inhibition attenuates early left ventricular enlargement after experimental myocardial infarction in mice.[J]. Circulation, 1999, 99 23: 3063-3070. DOI: 10.1161/01.cir.99.23.3063
[2] LU FANG . Differences in inflammation, MMP activation and collagen damage account for gender difference in murine cardiac rupture following myocardial infarction[J]. Journal of molecular and cellular cardiology, 2007, 43 5: Pages 535-544. DOI: 10.1016/j.yjmcc.2007.06.011 |
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Sigma-Aldrich
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Energy Chemical
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Merck KGaA
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www.sigmaaldrich.cn |
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