Sulfaphenazole Inhibitor CAS No. 526-08-9

Cat. No.	Name	Size	Price	Add Cart
KI0690	Sulfaphenazole	1 g	$400

Chemical Characteristic

Product Name	Sulfaphenazole
Synonyms	Sulfabid
CAS No.	526-08-9
Molecular Weight	314.36
Formula	C₁₅H₁₄N₄O₂S
Chemical Name	4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide
Smiles	c1(ccc(cc1)N)S(=O)(=O)Nc1n(ncc1)c1ccccc1
Chemical Structure

Biological activities

Sulfaphenazole is a sulfamide antibacterial. Sulfaphenazole acts as a strong, competitive inhibitor of CYP 2C9 with a Ki of 0.30µM. And sulfaphenazole acts as a ligand of high-affinity for CYP 2C9 iron with a Ks of 0.4µM. Sulfaphenazole is less potent toward CYP 2C8 and 2C18 with Ki of 63 and 29µM, respectively. Sulfaphenazole has inhibitory effects on several recombinant human liver cytochromes P450 expressed in yeast, including the four members of the CYP 2C subfamily present in human liver, CYP 2C8, 2C9, 2C18, and 2C19. ^[1] Besides, the mean IC50 for sulfaphenazole is 0.46µM for inhibition of flurbiprofen hydroxylation. Sulfaphenazole also inhibits phenytoin (PPH) hydroxylation with IC50 of 0.48 and 0.49µM, at PPH concentrations of 5µM and 10µM, respectively.^[2] Sulfaphenazole can significantly reduce infarct size and restore post ischemic coronary flow following ischemia and reperfusion while decreasing the generation of superoxide anions. Sulfaphenazole can attenuate post ischemic vascular dysfunction and restore NO-mediated endothelium- dependent vasoclilatation through the inhibition of CYP 2C activity. In vivo, sulfaphenazole restores endothelial-mediated relaxation in treated db/db mice, without affecting plasma glucose concentrations.^[3]

References

[1] Mancy A, et al. Interaction of sulfaphenazole derivatives with human liver cytochromes P450 2C: molecular origin of the specific inhibitory effects of sulfaphenazole on CYP 2C9 and consequences for the substrate binding site topology of CYP 2C9. Biochemistry. 1996, 35(50): 16205-16212. [2] Giancarlo GM, et al. Relative contributions of CYP2C9 and 2C19 to phenytoin 4-hydroxylation in vitro: inhibition by sulfaphenazole, omeprazole, and ticlopidine. Eur J Clin Pharmacol. 2001, 57 (1): 31-36. [3] Elmi S, et al. Sulfaphenazole treatment restores endothelium-dependent vasodilation in diabetic mice. Vascul Pharmacol. 2008, 48(1): 1-8.

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