Molecular structure of rac 8-Hydroxy Efavirenz, CAS Number: 205754-32-1
rac 8-Hydroxy Efavirenz (CAS 205754-32-1)
Alternate Names:
6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; 8-Hydroxyefavirenz
Application:
rac 8-Hydroxy Efavirenz is a metabolite of Efavirenz, a nonnucleoside HIV-1 reverse transcriptase inhibitor
CAS Number:
205754-32-1
Molecular Weight:
331.67
Molecular Formula:
C14H9ClF3NO3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
QUICK LINKS
Ordering Information
Description
Technical Information
Safety Information
SDS & Certificate of Analysis
rac 8-Hydroxy Efavirenz is a Efavirenz metabolite, a non-nucleoside HIV-1 reverse transcriptase inhibitor. In vitro studies have demonstrated its potent efficacy, with an EC50 value of 0.1 nM against HIV-1. Its mechanism of action involves inhibiting the reverse transcriptase enzyme of HIV-1 by selectively binding to a hydrophobic pocket adjacent to the enzyme′s active site. This interaction induces a significant conformational change in the reverse transcriptase enzyme, effectively impeding the synthesis of viral DNA from the viral RNA template.
rac 8-Hydroxy Efavirenz (CAS 205754-32-1) References
- The cytochrome P450 2B6 (CYP2B6) is the main catalyst of efavirenz primary and secondary metabolism: implication for HIV/AIDS therapy and utility of efavirenz as a substrate marker of CYP2B6 catalytic activity. | Ward, BA., et al. 2003. J Pharmacol Exp Ther. 306: 287-300. PMID: 12676886
- Metabolism of efavirenz and 8-hydroxyefavirenz by P450 2B6 leads to inactivation by two distinct mechanisms. | Bumpus, NN., et al. 2006. J Pharmacol Exp Ther. 318: 345-51. PMID: 16611850
- Impact of CYP2B6 polymorphism on hepatic efavirenz metabolism in vitro. | Desta, Z., et al. 2007. Pharmacogenomics. 8: 547-58. PMID: 17559344
- Efavirenz primary and secondary metabolism in vitro and in vivo: identification of novel metabolic pathways and cytochrome P450 2A6 as the principal catalyst of efavirenz 7-hydroxylation. | Ogburn, ET., et al. 2010. Drug Metab Dispos. 38: 1218-29. PMID: 20335270
- Contribution of N-glucuronidation to efavirenz elimination in vivo in the basal and rifampin-induced metabolism of efavirenz. | Cho, DY., et al. 2011. Antimicrob Agents Chemother. 55: 1504-9. PMID: 21282425
- Identification of human UGT isoforms responsible for glucuronidation of efavirenz and its three hydroxy metabolites. | Bae, SK., et al. 2011. Xenobiotica. 41: 437-44. PMID: 21319958
- Efavirenz and 8-hydroxyefavirenz induce cell death via a JNK- and BimEL-dependent mechanism in primary human hepatocytes. | Bumpus, NN. 2011. Toxicol Appl Pharmacol. 257: 227-34. PMID: 21958719
- Drug interaction of efavirenz and midazolam: efavirenz activates the CYP3A-mediated midazolam 1'-hydroxylation in vitro. | Keubler, A., et al. 2012. Drug Metab Dispos. 40: 1178-82. PMID: 22415932
- Dendritic spine injury induced by the 8-hydroxy metabolite of efavirenz. | Tovar-y-Romo, LB., et al. 2012. J Pharmacol Exp Ther. 343: 696-703. PMID: 22984227
- Population pharmacogenetic-based pharmacokinetic modeling of efavirenz, 7-hydroxy- and 8-hydroxyefavirenz. | Abdelhady, AM., et al. 2014. J Clin Pharmacol. 54: 87-96. PMID: 24142869
- Rifampin enhances cytochrome P450 (CYP) 2B6-mediated efavirenz 8-hydroxylation in healthy volunteers. | Cho, DY., et al. 2016. Drug Metab Pharmacokinet. 31: 107-16. PMID: 27053325
- Probing Ligand Structure-Activity Relationships in Pregnane X Receptor (PXR): Efavirenz and 8-Hydroxyefavirenz Exhibit Divergence in Activation. | Narayanan, B., et al. 2018. ChemMedChem. 13: 736-747. PMID: 29430850
- Effect of deglucuronidation on the results of the Basel phenotyping cocktail. | Bachmann, F., et al. 2021. Br J Clin Pharmacol. 87: 4608-4618. PMID: 33890704
- Pharmacogenetics of the Late-Onset Efavirenz Neurotoxicity Syndrome (LENS). | van Rensburg, R., et al. 2022. Clin Infect Dis. 75: 399-405. PMID: 34882770
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
rac 8-Hydroxy Efavirenz, 1 mg | sc-208270 | 1 mg | $357.00 | |||
rac 8-Hydroxy Efavirenz, 2 mg | sc-208270A | 2 mg | $637.00 | |||
rac 8-Hydroxy Efavirenz, 5 mg | sc-208270B | 5 mg | $1380.00 |