A major metabolite of efavirenz
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Parent Compound(s)
14412Efavirenz
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8-hydroxy Efavirenz

Item No. 27853

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S)-6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
CAS Number
205754-33-2
Molecular Formula
C14H9ClF3NO3
Formula Weight
331.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: solubleDMSO: solubleMethanol: soluble
SMILES
ClC1=CC(O)=C2C([C@@](C#CC3CC3)(C(F)(F)F)OC(N2)=O)=C1
InChi Code
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)
InChi Key
OOVOMPCQLMFEDT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $666

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    Product Description

    8-hydroxy Efavirenz is a major oxidative metabolite of the non-nucleoside reverse transcriptase inhibitor efavirenz (Item No. 14412).1 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.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Decloedt, E.H., and Maartens, G. Neuronal toxicity of efavirenz: A systematic review. Expert Opin. Drug Saf. 12(6), 841-846 (2013).

    2. Tovar-y-Romo, L.B., Bumpus, N.N., Pomerantz, D., et al. Dendritic spine injury induced by the 8-hydroxy metabolite of efavirenz. J. Pharmacol. Exp. Ther. 343(3), 696-703 (2012).