Efavirenz

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.

Efavirenz
Clinical data
Pronunciation/ɪˈfævɪrɛnz/ i-FAV-i-renz
Trade namesSustiva, Stocrin, others
AHFS/Drugs.comMonograph
MedlinePlusa699004
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth (capsules, tablets)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability40–45% (under fasting conditions)
Protein binding99.5–99.75%
MetabolismLiver (CYP2A6 and CYP2B6-mediated)
Onset of action3–5 hours
Elimination half-life40–55 hours
ExcretionKidney (14–34%) and feces (16–61%)
Identifiers
  • (4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.149.346
Chemical and physical data
FormulaC14H9ClF3NO2
Molar mass315.68 g·mol−1
3D model (JSmol)
SMILES
  • O=C1Nc2ccc(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1
  • 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 Y
  • Key:XPOQHMRABVBWPR-ZDUSSCGKSA-N Y
  (verify)

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.

Efavirenz was approved for medical use in the United States in 1998, and in the European Union in 1999. It is on the World Health Organization's List of Essential Medicines. As of 2016, it is available as a generic medication.

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