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Venlafaxine racemate
Venlafaxine racemate
Synonyms WY-45030
racemate.html Brand names Efexor, Effexor
IUPAC name

IUPAC name
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol
ChemSpider

5454

DrugBank

DB00285

PubChem

5656

PDB fields

N/A

Formula

C17H27NO2

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
InChIKey
InChIKey
PNVNVHUZROJLTJ-UHFFFAOYSA-N
SMILES
SMILES
CN(C)CC(C1=CC=C(C=C1)OC)C2(CCCCC2)O
(Jmol 3D structure)
Mol. mass

277.4018 g/mol

Venlafaxine is a serotonin-noradrenaline reuptake inhibitor (SNRI) that, at lower doses (<150 mg/day), serves as a selective serotonin reuptake inhibitor (SSRI), whereas at moderate doses it serves as an SNRI and at higher doses it serves as a serotonin-noradrenaline-dopamine reuptake inhibitor. It is believed to have superior efficacy to the SSRIs in relieving depression.[1] It is approved, in the developed world (Australia, the UK and the US included), for the treatment of: major depression, generalized anxiety disorder, panic disorder and social phobia.[2] It may also be used off-label to treat neuropathic pain, menopausal flushing, eating disorders, post-traumatic stress disorder (PTSD), attention-deficit/hyperactivity disorder (ADHD), obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder (PMDD) and to prevent tension headaches.[2] 

It is metabolized in the body into desvenlafaxine which has been relatively recently developed in itself for the treatment of depression.[3] Venlafaxine has an elimination half-life (t1/2) of just 5 hours, and its active metabolite, desvenlafaxine, has a half-life of 11 hours.[3] Consequently it would normally require to be dosed two or three times daily but most formulations marketed in the developed world release the drug more slowly (these formulations are called controlled release [CR], extended release [XR], modified release or sustained release [SR]), hence allowing once-daily dosing.[2] Due to its short half-life withdrawal effects are seen significantly sooner than with the SSRIs (as these agents have a half-life of >17 hours).[3]

StructureEdit

Venlafaxine structure in 2D and 3D
Venlafaxine racemate
(R)-venlafaxine
(S)-venlafaxine
400px (R)-venlafaxine
400px (S)-venlafaxine



External linksEdit

Reference listEdit

  1. de Silva, VA; Hanwella, R (January 2012). "Efficacy and tolerability of venlafaxine versus specific serotonin reuptake inhibitors in treatment of major depressive disorder: a meta-analysis of published studies.". International Clinical Psychopharmacology 27 (1): 8–16. PMID 21971532. doi:10.1097/YIC.0b013e32834ce13f. 
  2. 2.0 2.1 2.2 Brayfield, A, ed. (13 December 2013). "Venlafaxine Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 11 October 2014. 
  3. 3.0 3.1 3.2 Brunton, LL; Chabner, BA; Knollmann, BC, ed. (2010). Goodman & Gilman's Pharmacological Basis of Therapeutics. (12th ed.). New York, USA: McGraw-Hill Professional. ISBN 9780071624428. 

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