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UC166

Sigma-Aldrich

Sulfaphenazole

≥98% (HPLC)

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:
12352202
PubChem Substance ID:
24724643
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white to light yellow

mp

179-183 °C

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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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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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
BGBC1921V
023M3901V
023M3901
281-262V
BCBC9372

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Mahmood Khan et al.
Antioxidants & redox signaling, 11(4), 725-738 (2008-10-16)
The objective of this study was to establish the cardioprotective effect of sulfaphenazole (SPZ), a selective inhibitor of cytochrome P450 2C9 enzyme, in an in vivo rat model of acute myocardial infarction (MI). MI was induced by 30 min ligation
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
Shu-Ying Chang et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(12), 2513-2522 (2008-09-13)
Various groups have sought to determine the impact of CYP2C8 genotype (and CYP2C8 inhibition) on the pharmacokinetics (PK) of ibuprofen (IBU) enantiomers. However, the contribution of cytochrome P450 2C8 (CYP2C8) in human liver microsomes (HLMs) has not been reported. Therefore
Florian Krötz et al.
Cardiovascular research, 85(3), 542-550 (2009-09-01)
A CYP2C9-dependent endothelium-derived hyperpolarizing factor (EDHF) controls blood flow in many microvascular beds of various species by targeting vascular smooth muscle potassium channels. Since platelets express the same channels, we tested whether EDHF hyperpolarizes platelets and exerts an antithrombotic function
Takaki Toda et al.
Basic & clinical pharmacology & toxicology, 105(5), 327-332 (2009-08-12)
Fluvastatin has been considered to be metabolised to 5-hydroxy fluvastatin (M-2), 6-hydroxy fluvastatin (M-3) and N-desisopropyl fluvastatin (M-5) in human liver microsomes by primarily CYP2C9. To elucidate the contribution of different CYP enzymes on fluvastatin metabolism, we examined the effect
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