Venlafaxin

Venlafaxine

Clinical data
Trade names	Effexor, many generics
AHFS/Drugs.com	Monograph
License data	US DailyMed: b23637e5-d37f-41b5-ba76-fc053e903bc2
Pregnancy category	AU: B2 US: C (Risk not ruled out)
Routes of administration	by mouth
ATC code	N06AX16 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	42±15%
Protein binding	27±2% (parent compound), 30±12% (active metabolite, desvenlafaxine)
Metabolism	Hepatic (~50% of the parent compound is metabolised on first pass through the liver)
Biological half-life	5±2 h (parent compound for immediate release preparations), 15±6 h (parent compound for extended release preparations), 11±2 h (active metabolite)
Excretion	Renal (87%; 5% as unchanged drug; 29% as desvenlafaxine and 53% as other metabolites)
Identifiers
IUPAC name (RS)-1-[2-dimethylamino-1-(4-methoxyphenyl)-ethyl]cyclohexanol
CAS Number	93413-69-5 Y
PubChem CID	5656
DrugBank	DB00285 Y
ChemSpider	5454 Y
UNII	GRZ5RCB1QG
ChEBI	CHEBI:9943 Y
ChEMBL	CHEMBL637 Y
ECHA InfoCard	100.122.418
Chemical and physical data
Formula	C17H27NO2
Molar mass	277.402 g/mol
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES OC2(C(c1ccc(OC)cc1)CN(C)C)CCCCC2
InChI 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

Venlafaxine, sold under the brand name Effexor among others, is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. This means it increases the concentrations of the neurotransmitters serotonin and norepinephrine in the body and the brain. First introduced by Wyeth in 1993, now marketed by Pfizer, it is licensed for the treatment of major depressive disorder (MDD), generalised anxiety disorder (GAD), panic disorder and social phobia.

A comparative meta-analysis of 12 major antidepressants found that venlafaxine, mirtazapine, escitalopram, and sertraline were significantly more efficacious than duloxetine, fluoxetine, fluvoxamine, paroxetine, and reboxetine. A combination of venlafaxine and mirtazapine achieved remission rates (defined as a HAM-D score of 7 or less) of 58% in one controlled trial. In combination with an antipsychotic medicine aripiprazole, better results in treatment resistant depression in older adults have been demonstrated.

The rate of life-threatening or lethal outcomes for suicidal overdoses of venlafaxine is lower than for the TCAs, MAOIs, and bupropion but higher than all of the SSRIs, and equal to citalopram. It is metabolised in the body into another antidepressant drug called desvenlafaxine (O-desmethylvenlafaxine) which is also sold as an antidepressant, under the brand name Pristiq.