S0758

Sigma-Aldrich

Sulfaphenazole

≥98%

Synonym(s):
4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide
Empirical Formula (Hill Notation):
C15H14N4O2S
CAS Number:
Molecular Weight:
314.36
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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.

Packaging

1 g in poly bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
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)
Simon Lucas et al.
Journal of medicinal chemistry, 54(7), 2307-2319 (2011-03-10)
Pyridine substituted 3,4-dihydro-1H-quinolin-2-ones (e.g., 1-3) constitute a class of highly potent and selective inhibitors of aldosterone synthase (CYP11B2), a promising target for the treatment of hyperaldosteronism, congestive heart failure, and myocardial fibrosis. Among these, ethyl-substituted 3 possesses high selectivity against...
Ralf Heim et al.
Journal of medicinal chemistry, 51(16), 5064-5074 (2008-08-05)
Recently, we reported on the development of potent and selective inhibitors of aldosterone synthase (CYP11B2) for the treatment of congestive heart failure and myocardial fibrosis. A major drawback of these nonsteroidal compounds was a strong inhibition of the hepatic drug-metabolizing...
Altered purinergic signaling in uridine adenosine tetraphosphate-induced coronary relaxation in swine with metabolic derangement
Zhou Z, et al.
Purinergic Signaling, 13(3), 319-329 (2017)

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