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S0758

Sigma-Aldrich

Sulfaphenazole

≥98%

Sinónimos:

4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide

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About This Item

Fórmula empírica (notación de Hill):
C15H14N4O2S
Número de CAS:
526-08-9
Peso molecular:
314.36
EC Number:
208-384-3
MDL number:
MFCD00057226
UNSPSC Code:
12352204
PubChem Substance ID:
24278198
NACRES:
NA.77

assay

≥98%

form

powder

solubility

ethanol: 25 mg/mL, clear, colorless to yellow

storage temp.

2-8°C

SMILES string

Nc1ccc(cc1)S(=O)(=O)Nc2ccnn2-c3ccccc3

InChI

1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2

InChI key

QWCJHSGMANYXCW-UHFFFAOYSA-N

Gene Information

human ... CYP2C18(1562) , CYP2C19(1557) , CYP2C9(1559)

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Application

Sulfaphenazole has been used as a positive control to inhibit cytochrome P450 2C9 (cyp2c9) to quantify Rhodiola rosea inhibition. It has also been used as cytochrome P450 2C9 (cyp2c9) inhibitor in endothelial cells and microsomal preparations.

Biochem/physiol Actions

Antibacterial. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Inhibits bradykinin-induced tPA release.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Noncompetitive inhibition of human CYP 2C9 in vitro by a commercial Rhodiola rosea product
Thu OKF, et al.
Pharmacology Research & Perspectives, 5(4), e00324-e00324 (2017)
Accelerating Drug Discovery Efforts for Trypanosomatidic Infections Using an Integrated Transnational Academic Drug Discovery Platform
Moraes CB, et al.
SLAS discovery, 24(3), 346-361 (2019)
Simon Lucas et al.
Journal of medicinal chemistry, 51(24), 8077-8087 (2008-12-04)
Pyridine substituted naphthalenes (e.g., I-III) constitute a class of potent inhibitors of aldosterone synthase (CYP11B2). To overcome the unwanted inhibition of the hepatic enzyme CYP1A2, we aimed at reducing the number of aromatic carbons of these molecules because aromaticity has
Simon Lucas et al.
Journal of medicinal chemistry, 51(19), 6138-6149 (2008-09-04)
Pharmacophore modeling of a series of aldosterone synthase (CYP11B2) inhibitors triggered the design of compounds 11 and 12 by extending a previously established naphthalene molecular scaffold (e.g., present in molecules 1 and 2) via introduction of a phenyl or benzyl
Chengqun Huang et al.
American journal of physiology. Heart and circulatory physiology, 298(2), H570-H579 (2009-12-17)
Previously, we showed that sulfaphenazole (SUL), an antimicrobial agent that is a potent inhibitor of cytochrome P4502C9, is protective against ischemia-reperfusion (I/R) injury (Ref. 15). The mechanism, however, underlying this cardioprotection, is largely unknown. With evidence that activation of autophagy
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