Structure via PubChem · Public domain (PubChem)
efavirenz
Sign in to saveAlso known as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one, (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one, (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one, 6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one
Efavirenz (EFV), sold under the brand names Sustiva among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needlestick injury or other potential exposure. It is sold both by itself and in combination as efavirenz/emtricitabine/tenofovir. It is taken by mouth.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 458955867
- Drug.image
- Efavirenz.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Efavirenz ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 150px
- Drug.pronounce
- or
- Drug.tradename
- Sustiva, Stocrin, others
- Drug.MedlinePlus
- a699004
- Drug.DailyMedID
- Efavirenz
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth (capsules, tablets)
- Drug.ATC_prefix
- J05
- Drug.ATC_suffix
- AG03
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C14H9ClF3NO2
- Molecular weight
- 315.67 g/mol
- IUPAC name
- (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
- SMILES
- C1CC1C#C[C@]2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
- InChIKey
- XPOQHMRABVBWPR-ZDUSSCGKSA-N
- XLogP
- 4
- Polar surface area
- 38.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
5,803 papers- Efavirenz: History, Development and Future.Biomolecules · 2022
- Efavirenz.Drugs · 1998
- Efavirenz as a psychotropic drug.European review for medical and pharmacological sciences · 2020
- Efavirenz Metabolism: Influence of Polymorphic CYP2B6 Variants and Stereochemistry.Drug metabolism and disposition: the biological fate of chemicals · 2019
- Efavirenz.Expert opinion on pharmacotherapy · 2007
via PubMed
Wikidata facts
- Mass
- 315.027
Show 6 more facts
- chemical formula
- C₁₄H₉ClF₃NO₂
- Commons category
- Efavirenz
- World Health Organisation international non-proprietary name
- efavirenz
- isomeric SMILES
- C1CC1C#C[C@]2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
- canonical SMILES
- C1CC1C#CC2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
- defined daily dose
- 0.6
Sources (8)
via Wikidata · CC0
~12 min read
Article
17 sectionsContents
- Medical uses
- Pregnancy and breastfeeding
- Contraindications
- Adverse effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Anti-HIV effects
- Neuropsychiatric effects
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Pricing information
- Recreational use
- Brands
- References
Efavirenz (EFV), sold under the brand names Sustiva among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needlestick injury or other potential exposure. It is sold both by itself and in combination as efavirenz/emtricitabine/tenofovir. It is taken by mouth.
Common side effects include rash, nausea, headache, feeling tired, and trouble sleeping. Some of the rashes may be serious such as Stevens–Johnson syndrome. Other serious side effects include depression, thoughts of suicide, liver problems, and seizures. It is not safe for use during pregnancy. It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and works by blocking the function of reverse transcriptase.