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SML0536

Sigma-Aldrich

Efavirenz

≥98% (HPLC)

Synonym(s):

Efavirenz, (4S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one

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About This Item

Empirical Formula (Hill Notation):
C14H9ClF3NO2
CAS Number:
154598-52-4
Molecular Weight:
315.67
MDL number:
MFCD05662344
UNSPSC Code:
12352200
PubChem Substance ID:
329825539
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -90 to -100°, c = 1 in methanol

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

ClC1=CC=C2C([C@@](C#CC3CC3)(C(F)(F)F)OC(N2)=O)=C1

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)/t13-/m0/s1

InChI key

XPOQHMRABVBWPR-ZDUSSCGKSA-N

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General description

Efavirenz, commercially known as Sustiva™ is a polycyclic aromatic hydrocarbon with benzene and oxazinan-2-one chromophores.

Application

Efavirenz has been used:
  • to assess its anti-porcine endogenous retrovirus (PERV) activity
  • in cytotoxicity assay
  • to investigate the solute-solvent effects of efavirenz by means combined time-dependent density functional theory (TD-DFT) and spectroscopic calculations

Biochem/physiol Actions

Efavirenz is a nonnucleoside reverse transcriptase inhibitor (NNRTI). It is an anti-HIV drug, commonly used in combination therapy for AIDs treatment. It is part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Legal Information

Sustiva is a trademark of E. I. du Pont de Nemours and Company

Signal Word

Danger

Hazard Statements

H302,H360,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pietro Vernazza et al.
Journal of acquired immune deficiency syndromes (1999), 62(2), 171-179 (2013-01-19)
A 96-week clinical study was planned to estimate the antiviral activity and safety of lersivirine in treatment-naive HIV-1-infected patients. This ongoing international, multicenter, double-blind, randomized, Phase IIb exploratory study evaluates the efficacy and safety of 2 doses of lersivirine or
Kyle W Anderson et al.
The Journal of biological chemistry, 291(22), 11876-11886 (2016-04-09)
Cytochrome P450 46A1 (CYP46A1) is a microsomal enzyme and cholesterol 24-hydroxylase that controls cholesterol elimination from the brain. This P450 is also a potential target for Alzheimer disease because it can be activated pharmacologically by some marketed drugs, as exemplified
Jürgen K Rockstroh et al.
Journal of acquired immune deficiency syndromes (1999), 63(1), 77-85 (2013-02-16)
STARTMRK, a phase III noninferiority trial of raltegravir-based versus efavirenz-based therapy in treatment-naive patients, remained blinded until its conclusion at 5 years. We now report the final study results. Previously untreated patients without baseline resistance to efavirenz, tenofovir, or emtricitabine
Michael M Lübtow et al.
Biomacromolecules, 20(8), 3041-3056 (2019-07-19)
Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as "like-dissolves-like" or hydrophilic/hydrophobic. However, polymer-drug compatibility strongly affects formulation properties and therefore the translation
Sho Sudo et al.
Journal of virology, 87(6), 3348-3360 (2013-01-11)
Efavirenz (EFV), a nonnucleoside reverse transcriptase (RT) inhibitor, also inhibits HIV-1 particle release through enhanced Gag/Gag-Pol processing by protease (PR). To better understand the mechanisms of the EFV-mediated enhancement of Gag processing, we examined the intracellular localization of Gag/Gag-Pol processing
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