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205754-33-2

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205754-33-2 Usage

Description

8-hydroxy Efavirenz is a major oxidative metabolite of the non-nucleoside reverse transcriptase inhibitor efavirenz . 8-hydroxy Efavirenz is formed when efavirenz is metabolized by the cytochrome P450 (CYP) isoform CYP2B6. It induces apoptosis in rat primary hippocampal neurons and loss of dendritic spines in rat primary hippocampal neuronal cultures when used at a concentration of 0.01 μM.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 205754-33-2 differently. You can refer to the following data:
1. A labellebed metabolite of Efavirenz, a nonnucleoside HIV-1 reverse transcriptase inhibitor
2. 8-Hydroxy Efavirenz is a metabolite of Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor.

Check Digit Verification of cas no

The CAS Registry Mumber 205754-33-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,5,7,5 and 4 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 205754-33:
(8*2)+(7*0)+(6*5)+(5*7)+(4*5)+(3*4)+(2*3)+(1*3)=122
122 % 10 = 2
So 205754-33-2 is a valid CAS Registry Number.

205754-33-2Downstream Products

205754-33-2Relevant articles and documents

Late-Stage Aromatic C-H Oxygenation

B?rgel, Jonas,Tanwar, Lalita,Berger, Florian,Ritter, Tobias

supporting information, p. 16026 - 16031 (2018/12/13)

Synthetic methods for oxidative aromatic C-O bond formation are sparse, despite their demand in metabolite synthesis for drug discovery and development. We report a novel methodology for late-stage C-O bond formation of arenes. The reaction proceeds with excellent functional group tolerance even for highly functionalized substrates. The resulting aryl mesylates provide access to potential human metabolites of pharmaceuticals, and may be used directly to install a C-F bond to block metabolic hotspots. A charge-transfer interaction between the reagent bis(methanesulfonyl) peroxide and the substrate arenes may be relevant for the chemoselective functionalization of arenes over other functional groups.

Characterization of marmoset CYP2B6: CDNA cloning, protein expression and enzymatic functions

Mayumi, Kei,Hanioka, Nobumitsu,Masuda, Kazufumi,Koeda, Akiko,Naito, Shinsaku,Miyata, Atsuro,Narimatsu, Shizuo

, p. 1182 - 1194 (2013/05/09)

The common marmoset is a promising species for evaluating the safety of drug candidates. To further understand the capacity for drug metabolism in marmosets, a cDNA encoding a CYP2B enzyme was cloned from the total RNA fraction of marmoset liver by 3′- and 5′-RACE methods. Nucleotide and deduced amino acid sequences showed 90.8 and 86.2% identity, respectively, with human CYP2B6. The marmoset CYP2B6 (marCYP2B6) protein was expressed in insect cells, and its enzymatic properties were compared with those of human (humCYP2B6) and cynomolgus monkey (cynCYP2B6) orthologs in liver and insect cell microsomes. Enzymatic functions were examined for the oxidation of 7-ethoxy-4-(trifluoromethyl)coumarin (7-ETC), bupropion (BUP) and efavirenz (EFV). The kinetic profiles for the oxidation of the three substrates by liver microsomal fractions were similar between humans and cynomolgus monkeys (biphasic for 7-ETC and monophasic for BUP and EFV), but that of marmosets was unique (monophasic for 7-ETC and biphasic for BUP and EFV). Recombinant enzymes, humCYP2B6 and cynCYP2B6, also yielded similar kinetic profiles for the oxidation of the three substrates, whereas marCYP2B6 showed activity only for 7-ETC hydroxylation. In silico docking simulations suggested that two amino acid residues, Val-114 and Leu-367, affect the activity of marCYP2B6. In fact, a marCYP2B6 mutant with substitutions V114I and L367V exhibited BUP hydroxylase activity that was 4-fold higher than that of humCYP2B6, while its EFV 8-hydroxylase activity was only 10% that of the human enzyme. These results indicate that the amino acids at positions 114 and 367 affect the enzymatic capacity of marmoset CYP2B6.

Synthesis and biological activities of potential metabolites of the non-nucleoside reverse transcriptase inhibitor efavirenz

Markwalder, Jay A.,Christ, David D.,Mutlib, Abdul,Cordova, Beverly C.,Klabe, Ronald M.,Seitz, Steven P.

, p. 619 - 622 (2007/10/03)

Studies on the biotransformation of the clinically important non-nucleoside reverse transcriptase inhibitor efavirenz have shown that oxidation and secondary conjugation are important components of the processing of this molecule in vivo. We have synthesized metabolites of efavirenz to confirm their structure and to evaluate their activity as antivirals.

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