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Merck

S0758

Sulfaphenazole

≥98%, CYP2C9 inhibitor, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H14N4O2S
CAS Number:
526-08-9
Molecular Weight:
314.36
NACRES:
NA.77
PubChem Substance ID:
24278198
UNSPSC Code:
12352204
EC Number:
208-384-3
MDL number:
MFCD00057226

Product Name

Sulfaphenazole, ≥98%

InChI key

QWCJHSGMANYXCW-UHFFFAOYSA-N

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

SMILES string

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

assay

≥98%

form

powder

solubility

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

storage temp.

2-8°C

Quality Level

100

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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000508715
0000508715
0000436070
0000436070
0000368519

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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)
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
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
Vienna E Brunt et al.
The Journal of physiology, 590(15), 3523-3534 (2012-06-08)
While it is accepted that NO is responsible for ∼60% of the plateau in cutaneous thermal hyperaemia, a large portion of the response remains unknown. We sought to determine whether the remaining ∼40% could be attributed to EDHF-mediated activation of
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