A non-nucleoside reverse transcriptase inhibitor
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Active Metabolite(s)
278538-hydroxy Efavirenz
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Efavirenz

Item No. 14412

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S)-6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one
CAS Number
154598-52-4
Synonyms
  • DMP 266
  • EFV
  • L-743,726
Molecular Formula
C14H9ClF3NO2
Formula Weight
315.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 14 mg/mlEthanol: 20 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.50 mg/ml
λmax
247, 294 nm
SMILES
ClC1=CC=C2C([C@@](C#CC3CC3)(C(F)(F)F)OC(N2)=O)=C1
InChi Code
InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)
InChi Key
XPOQHMRABVBWPR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Efavirenz is a non-nucleoside reverse transcriptase inhibitor (NNRTI) that binds to wild-type and mutant HIV-1 RTs (Kis = 2.93 and 3.85-56.5 nM, respectively).1 It inhibits wild-type and mutant HIV-1 viral replication in MT-4 human T lymphoid cells (IC95s = 1.5-1,500 nM). Efavirenz also prevents RNA plus-strand initiation with an IC50 value of 17 nM.2 In vivo, efavirenz reduces HIV-1 cDNA in spleen of HIV-1-challenged HIV-susceptible transgenic rats.3 Formulations containing efavirenz have been used in combination therapy for the treatment of HIV-1.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Young, S.D., Britcher, S.F., Tran, L.O., et al. L-743,726 (DMP-266): A novel, highly potent nonnucleoside inhibitor of the human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother. 39(12), 2602-2605 (1995).

    2. Grobler, J.A., Dornadula, G., Rice, M.R., et al. HIV-1 reverse transcriptase plus-strand initiation exhibits preferential sensitivity to non-nucleoside reverse transcriptase inhibitors in vitro. The Journal of Biological Chemisty 282(11), 8005-8010 (2007).

    3. Goffinet, C., Allespach, I., and Keppler, O.T. HIV-susceptible transgenic rats allow rapid preclinical testing of antiviral compounds targeting virus entry or reverse transcription. Proc. Natl. Acad. Sci. USA 104(3), 1015-1020 (2007).

    4. Sheran, M. The nonnucleoside reverse transcriptase inhibitors efavirenz and nevirapine in the treatment of HIV. HIV Clin.Trials 6(3), 158-168 (2005).

    5. Rakhmanina, N.Y., and van den Anker, J.N. Efavirenz in the therapy of HIV infection. Expert Opin. Drug Metab. Toxicol. 6(1), 95-103 (2010).