Venlafaxine

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 quality of life. It may also be used for chronic pain. It is taken by mouth. It is also available as the salt venlafaxine besylate in an extended-release formulation (Venbysi XR).

Venlafaxine
Clinical data
Pronunciation/ˌvɛnləˈfæksn/
VEN-lə-FAK-seen
Trade namesEffexor, Efexor, Venbysi XR, others
AHFS/Drugs.comMonograph
MedlinePlusa694020
License data
Pregnancy
category
  • AU: B2
Routes of
administration
By mouth
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)

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. There are concerns that use during the later part of pregnancy can harm the baby. How it works 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 2021, it was the 44th most commonly prescribed medication in the United States with more than 15 million prescriptions.

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