8-Hydroxyefavirenz

• CAT Number: R041719
• CAS Number: 205754-33-2
• Molecular Formula: C14H9ClF3NO3
• Molecular Weight: 331.67
• Purity: ≥95%
• Synonyms: (4S)-6-chloro-4-(2-cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• 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: C1CC1C#CC2(C3=C(C(=CC(=C3)Cl)O)NC(=O)O2)C(F)(F)F

8-Hydroxyefavirenz (8-OH-EFV) is a primary metabolite of (HY-10572). 8-Hydroxyefavirenz induces apoptosis via a JNK- and BimEL-dependent mechanism in primary human hepatocytes. 8-Hydroxyefavirenz can be used in research of cancer[1]. 8-Hydroxyefavirenz is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
8-Hydroxyefavirenz (8-OH-EFV; 1-10 μM; 3-24 h; primary human hepatocytes) increases cell death in a time- and concentration-dependent manner and induces caspase-3 activity beginning at 6 h[1].
8-Hydroxyefavirenz (1-10 μM; 6-24 h) stimulates mitochondria ROS production in primary human hepatocytes[1].
8-Hydroxyefavirenz (10 μM; 3-24 h) activates JNK and increases the ratio of phosphorylated JNK to total JNK by 4.2-fold. 8-Hydroxyefavirenz increases the mRNA and protein expression of BimEL[1].

Reference

[1]. Bumpus NN. Efavirenz and 8-hydroxyefavirenz induce cell death via a JNK- and BimEL-dependent mechanism in primary human hepatocytes. Toxicol Appl Pharmacol. 2011 Dec 1;257(2):227-34.
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