RAC 8-HYDROXY EFAVIRENZ Chemical Properties

Melting point:

144-154°C

Boiling point:

373.6±42.0 °C(Predicted)

Density 

1?+-.0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Acetonitrile: soluble; DMSO: soluble; Methanol: soluble

form 

A solid

pka

7.18±0.40(Predicted)

color 

White to off-white

InChI

InChI=1S/C14H9ClF3NO3/c15-8-5-9-11(10(20)6-8)19-12(21)22-13(9,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)/t13-/m0/s1

InChIKey

OOVOMPCQLMFEDT-ZDUSSCGKSA-N

SMILES

N1C2=C(O)C=C(Cl)C=C2[C@@](C#CC2CC2)(C(F)(F)F)OC1=O

RAC 8-HYDROXY EFAVIRENZ Usage And Synthesis

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

A labellebed metabolite of Efavirenz, a nonnucleoside HIV-1 reverse transcriptase inhibitor

Uses

8-Hydroxy Efavirenz is a metabolite of Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor.

References

[1] ERIC H DECLOEDT G M. Neuronal toxicity of efavirenz: a systematic review.[J]. Expert Opinion on Drug Safety, 2013, 12 6: 841-846. DOI: 10.1517/14740338.2013.823396
[2] LUIS B TOVAR-Y ROMO. Dendritic spine injury induced by the 8-hydroxy metabolite of efavirenz.[J]. Journal of Pharmacology and Experimental Therapeutics, 2012, 343 3: 696-703. DOI: 10.1124/jpet.112.195701

RAC 8-HYDROXY EFAVIRENZ(205754-33-2)Related Product Information

• SE 563
• Efavirenz AMino Alcohol Ethyl CarbaMate
• rac Methyl Efavirenz
• Efavirenz Related Compound B (15 mg) ((S,E)-6-Chloro-4-(2-Cyclopropylvinyl)-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one)
• rac 8-Hydroxy Efavirenz
• Efavirenz Related Compound C (20 mg) (6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline)
• 6-chloro-4-pent-1-ynyl-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• L 741211
• Efavirenz
• rac 8,14-Dihydroxy Efavirenz
• (S)-1-(2-Amino-5-chlorophenyl)-1-(trifluoromethyl)-3-cyclopropyl-2-propyn-1-ol
• (4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2H-3,1-benzoxazine(Mixture of 2 Diastereomers)
• Efavirenz IP Impurity A
• rac 7-Hydroxy Efavirenz
• [4-Chloro-2-[(1S)-3-cyclopropyl-1-hydroxy-1-(trifluoromethyl)-2-propynyl)phenyl]carbamic Acid Methyl Ester
• (S)-5-chloro-a-(Cyclopropylacetenyl)-2-[((4-methoxyphenyl)methyl)amino]-a- (trifluoromethyl) benzenemethanol (E-4)
• Enantiomer Efavirenz
• Efavirenz Impurity 13(7-Hydroxy Efavirenz)