3-Hydroxy Nevirapine

• CAT Number: R013062
• CAS Number: 174532-82-2
• Molecular Formula: C15H14N4O2
• Molecular Weight: 282.303
• Purity: 98%
• Storage: Store at RT
• IUPAC Name: 2-cyclopropyl-6-hydroxy-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
• InChI: InChI=1S/C15H14N4O2/c1-8-11(20)7-17-14-12(8)18-15(21)10-3-2-6-16-13(10)19(14)9-4-5-9/h2-3,6-7,9,20H,4-5H2,1H3,(H,18,21)
• InChIKey: DANIONWINZEYME-UHFFFAOYSA-N
• SMILES: CC1=C2C(=NC=C1O)N(C3=C(C=CC=N3)C(=O)N2)C4CC4

3-Hydroxy Nevirapine(CAS 174532-82-2) is a metabolites of nevirapine. 

Reference

1. Antimicrob Agents Chemother. 2013 May;57(5):2154-60. doi: 10.1128/AAC.02294-12. Epub 2013 Mar 4.
Pharmacokinetics of phase I nevirapine metabolites following a single dose and at steady state.
Fan-Havard P(1), Liu Z, Chou M, Ling Y, Barrail-Tran A, Haas DW, Taburet AM; ANRS12154 Study Group.
Author information:
(1)School of Pharmacy and Pharmaceutical Sciences, University at Buffalo, Amherst, New York, USA.
Nevirapine is one of the most extensively prescribed antiretrovirals worldwide. The present analyses used data and specimens from two prior studies to characterize and compare plasma nevirapine phase I metabolite profiles following a single 200-mg oral dose of nevirapine in 10 HIV-negative African Americans and a steady-state 200-mg twice-daily dose in 10 HIV-infected Cambodians. Nevirapine was assayed by high-performance liquid chromatography (HPLC). The 2-, 3-, 8- and 12-hydroxy and 4-carboxy metabolites of nevirapine were assayed by liquid chromatography-tandem mass spectrometry (LC/MS/MS). Pharmacokinetic parameters were calculated by noncompartmental analysis. The metabolic index for each metabolite was defined as the ratio of the metabolite area under the concentration-time curve (AUC) to the nevirapine AUC. Every metabolite concentration was much less than the corresponding nevirapine concentration. The predominant metabolite after single dose and at steady state was 12-hydroxynevirapine. From single dose to steady state, the metabolic index increased for 3-hydroxynevirapine (P < 0.01) but decreased for 2-hydroxynevirapine (P < 0.001). The 3-hydroxynevirapine metabolic index was correlated with nevirapine apparent clearance (P < 0.001). These findings are consistent with induction of CYP2B6 (3-hydroxy metabolite) and a possible inhibition of CYP3A (2-hydroxy metabolite), although these are preliminary data. There were no such changes in metabolic indexes for 12-hydroxynevirapine or 4-carboxynevirapine. Two subjects with the CYP2B6 *6*6 genetic polymorphism had metabolic indexes in the same range as other subjects. These results suggest that nevirapine metabolite profiles change over time under the influence of enzyme induction, enzyme inhibition, and host genetics. Further work is warranted to elucidate nevirapine biotransformation pathways and implications for drug efficacy and toxicity.