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Merck
CN

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
EC Number:
208-384-3
MDL number:
MFCD00057226
UNSPSC Code:
12352204
PubChem Substance ID:
24278198
NACRES:
NA.77

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Product Name

Sulfaphenazole, ≥98%

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000508715
0000508715
0000436070
0000436070
0000368519

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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(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
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)
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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