Venlafaxine

Venlafaxine
Clinical data
Pronunciation/ˌvɛnləˈfæksn/
ven-lə-FAK-seen
Trade namesEffexor, others
AHFS/Drugs.comMonograph
MedlinePlusa694020
License data
Pregnancy
category
  • AU: B2
Routes of
administration
Oral
Drug classSerotonin–norepinephrine reuptake inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability42±15%
Protein binding27±2% (parent compound), 30±12% (active metabolite, desvenlafaxine)
MetabolismExtensively metabolised by the liver, primarily via CYP2D6
MetabolitesO-desmethylvenlafaxine (ODV), see desvenlafaxine
Elimination half-life5±2 h (parent compound for immediate release preparations), 15±6 h (parent compound for extended-release preparations), 11±2 h (active metabolite)
ExcretionKidney (87%; 5% as unchanged drug; 29% as desvenlafaxine and 53% as other metabolites)
Identifiers
  • (RS)-1-[2-dimethylamino-1-(4-methoxyphenyl)-ethyl]cyclohexanol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.122.418
Chemical and physical data
FormulaC17H27NO2
Molar mass277.408 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • OC2(C(c1ccc(OC)cc1)CN(C)C)CCCCC2
  • InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3 Y
  • Key:PNVNVHUZROJLTJ-UHFFFAOYSA-N Y
  (verify)

Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin–norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic disorder, and social anxiety disorder. Studies have shown that venlafaxine improves post-traumatic stress disorder (PTSD) as a recommended first-line treatment. It may also be used for chronic neuropathic pain. It is taken orally (swallowed by mouth). It is also available as the salt venlafaxine besylate (venlafaxine benzenesulfonate monohydrate) in an extended-release formulation (Venbysi XR).

Common side effects include loss of appetite, constipation, dry mouth, dizziness, sweating, insomnia, drowsiness and sexual problems. Severe side effects include an increased risk of suicide, mania, and serotonin syndrome. Antidepressant withdrawal syndrome may occur if stopped. A meta-analysis of randomized trials in depression found an increased rate of serious adverse events, particularly sexual dysfunction and anorexia, and several non-serious adverse effects, including nervousness, asthenia, and tremor. There are concerns that use during the later part of pregnancy can harm the baby. Venlafaxine's mechanism of action is not entirely clear, but it seems to be related to the potentiation of the activity of some neurotransmitters in the brain.

Venlafaxine was approved for medical use in the United States in 1993. It is available as a generic medication. In 2022, it was the 44th most commonly prescribed medication in the United States, with more than 13 million prescriptions.