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Venlafaxine information


Venlafaxine
Clinical data
Pronunciation/ˌvɛnləˈfæksn/
VEN-lə-FAK-seen
Trade namesEffexor, Efexor, Venbysi XR, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa694020
License data
  • US DailyMed: Venlafaxine
Pregnancy
category
  • AU: B2[2]
Routes of
administration
By mouth
Drug classSerotonin–norepinephrine reuptake inhibitor
ATC code
  • N06AX16 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[2]
  • BR: Class C1 (Other controlled substances)[4]
  • CA: ℞-only
  • UK: POM (Prescription only)[5]
  • US: WARNING[3]Rx-only[6][7]
Pharmacokinetic data
Bioavailability42±15%[2]
Protein binding27±2% (parent compound), 30±12% (active metabolite, desvenlafaxine)[6]
MetabolismExtensively metabolised by the liver,[2][6] primarily via CYP2D6[8]
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)[2][6]
ExcretionKidney (87%; 5% as unchanged drug; 29% as desvenlafaxine and 53% as other metabolites)[2][6]
Identifiers
IUPAC name
  • (RS)-1-[2-dimethylamino-1-(4-methoxyphenyl)-ethyl]cyclohexanol
CAS Number
  • 93413-69-5 checkY
  • as HCl: 99300-78-4
PubChem CID
  • 5656
  • as HCl: 62923
DrugBank
  • DB00285 checkY
  • as HCl: DBSALT000186
ChemSpider
  • 5454 checkY
  • as HCl: 56641
UNII
  • GRZ5RCB1QG
  • as HCl: 7D7RX5A8MO
KEGG
  • D08670 checkY
  • as HCl: D00821
ChEBI
  • CHEBI:9943 checkY
  • as HCl: CHEBI:9944
ChEMBL
  • ChEMBL637 checkY
  • as HCl: ChEMBL1201066
CompTox Dashboard (EPA)
  • DTXSID6023737 Edit this at Wikidata
ECHA InfoCard100.122.418 Edit this at Wikidata
Chemical and physical data
FormulaC17H27NO2
Molar mass277.408 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic 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 checkY
  • Key:PNVNVHUZROJLTJ-UHFFFAOYSA-N checkY
  (verify)

Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin–norepinephrine reuptake inhibitor (SNRI) class.[6][9] It is used to treat major depressive disorder, generalized anxiety disorder, panic disorder, and social anxiety disorder.[9] Studies have shown that venlafaxine improves post-traumatic stress disorder (PTSD).[10] It may also be used for chronic pain.[11] It is taken by mouth.[9] It is also available as the salt venlafaxine besylate in an extended-release formulation (Venbysi XR).[7]

Common side effects include loss of appetite, constipation, dry mouth, dizziness, sweating, insomnia, drowsiness and sexual problems.[9] Severe side effects include an increased risk of suicide, mania, and serotonin syndrome.[9] Antidepressant withdrawal syndrome may occur if stopped.[9] There are concerns that use during the later part of pregnancy can harm the baby.[9] 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.[9]

Venlafaxine was approved for medical use in the United States in 1993.[9] It is available as a generic medication.[9] In 2021, it was the 44th most commonly prescribed medication in the United States with more than 15 million prescriptions.[12][13]

  1. ^ Cite error: The named reference brands was invoked but never defined (see the help page).
  2. ^ a b c d e f Cite error: The named reference TGA was invoked but never defined (see the help page).
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  5. ^ "Efexor XL 75 mg hard prolonged release capsules - Summary of Product Characteristics (SmPC)". (emc). 16 March 2020. Archived from the original on 7 October 2020. Retrieved 15 April 2020.
  6. ^ a b c d e f "Effexor XR- venlafaxine hydrochloride capsule, extended release". DailyMed. Archived from the original on 12 May 2021. Retrieved 11 May 2021.
  7. ^ a b "Venlafaxine tablet, extended release". DailyMed. 30 June 2022. Retrieved 7 January 2023.
  8. ^ Dean L (2015). Pratt VM, Scott SA, Pirmohamed M, Esquivel B, Kane MS, Kattman BL, Malheiro AJ (eds.). Venlafaxine Therapy and CYP2D6 Genotype. National Center for Biotechnology Information (US). PMID 28520361. Archived from the original on 29 November 2017. Retrieved 28 December 2018.
  9. ^ a b c d e f g h i j "Venlafaxine Hydrochloride Monograph for Professionals". Drugs.com. AHFS. Archived from the original on 27 November 2020. Retrieved 24 December 2018.
  10. ^ Forman-Hoffman V, Middleton JC, Feltner C, Gaynes BN, Weber RP, Bann C, et al. (17 May 2018). Psychological and Pharmacological Treatments for Adults With Posttraumatic Stress Disorder: A Systematic Review Update (Report). Agency for Healthcare Research and Quality (AHRQ). doi:10.23970/ahrqepccer207 (inactive 4 March 2024). PMID 30204376. Archived from the original on 10 July 2018. Retrieved 29 July 2023.{{cite report}}: CS1 maint: DOI inactive as of March 2024 (link)
  11. ^ "Antidepressants: Another weapon against chronic pain". Mayo Clinic. Archived from the original on 26 October 2021. Retrieved 25 January 2020.
  12. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  13. ^ "Venlafaxine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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List of adverse effects of venlafaxine

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following list shows the rates of adverse symptoms seen in people taking venlafaxine. Headache — an often transient side effect that is common to most serotonin...

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Antidepressant discontinuation syndrome

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SNRI venlafaxine has been reported to have a higher incidence in withdrawal symptoms after discontinuation when compared to other SNRIs.Venlafaxine has...

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Desvenlafaxine

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occasionally reassessed. It may be less effective than its parent compound venlafaxine, although some studies have found comparable efficacy. Common side effects...

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Phantosmia

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treated with the use of an anti depressive medication by the common name Venlafaxine (Effexor). The relation between mood disorders and phantosmia is unknown...

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Antidepressant

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demographic. Fluoxetine and venlafaxine are used off-label. Fluoxetine has produced unsatisfactory mixed results. Venlafaxine showed response rates of 78%...

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Attention deficit hyperactivity disorder

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Duloxetine Imipramine Milnacipran Moclobemide Nortriptyline Reboxetine Venlafaxine Miscellaneous/others Amantadine Carbamazepine Related articles Attention...

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Selective serotonin reuptake inhibitor

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nefazodone, and the serotonin and norepinephrine reuptake inhibitor (SNRI) venlafaxine). The authors attributed the relationship between severity and efficacy...

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Anxiolytic

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market. The first serotonin norepinephrine reuptake inhibitor (SNRI), venlafaxine (Effexor), entered the market in 1993. SNRIs can target serotonin and...

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Flaxen

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elimia, a species of freshwater snail, Elimia boykiniana a brand name of Venlafaxine, an antidepressant Flax Flax (disambiguation) This disambiguation page...

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Cocaine

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Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Threohydrobupropion Tripelennamine Venlafaxine...

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C17H27NO2

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277.204179 u) may refer to: ICI-118,551 Padimate O PNU-99,194 RDS-127 Venlafaxine This set index page lists chemical structure articles associated with...

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Mirtazapine

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should be given when combined with fluvoxamine. There is a combination of venlafaxine and mirtazapine, sometimes referred to as "California rocket fuel". Several...

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MDMA

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Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine See also: Receptor/signaling modulators...

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Effector

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Electronic Frontier Foundation Effexor, a brand name for the antidepressant venlafaxine Bacterial effector protein, proteins secreted by bacterial pathogens...

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Diabetic neuropathy

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further analysis of previous studies showed that the agents carbamazepine, venlafaxine, duloxetine, and amitriptyline were more effective than placebo, but...

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Methamphetamine

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Witzelsucht

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and antimanic agents. Serotonin and norepinephrine reuptake inhibitor, venlafaxine, were given to case study KS four months after initial stroke that started...

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Allodynia

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Methylprednisone (intrathecal) Adenosine Glycine antagonist Desipramine Venlafaxine Pregabalin Static mechanical allodynia – sodium channel blockers, opioids...

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Duloxetine

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treatments along with citalopram, escitalopram, sertraline, paroxetine, and venlafaxine. Duloxetine was approved for the pain associated with diabetic peripheral...

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Chlorphenamine

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Chloroacetyl chloride

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aluminium chloride catalyst: With anisole, it is used for the synthesis of venlafaxine. Like other acyl chlorides, reaction with other protic compounds such...

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Cataplexy

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like paralysis during the day. If the above treatment is not possible, venlafaxine is recommended. Evidence for benefit is not as good.[clarification needed]...

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Amphetamine

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Generalized anxiety disorder

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g., cannabis, citalopram, escitalopram, sertraline, duloxetine, and venlafaxine). CBT and selective serotonin reuptake inhibitors (SSRIs) are first-line...

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Peripheral neuropathy

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List of antidepressants

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(Cymbalta) Levomilnacipran (Fetzima) Milnacipran (Ixel, Savella, Milnaneurax) Venlafaxine (Effexor, Trevilor) Toludesvenlafaxine (Ruoxinlin) Nefazodone (Serzone)...

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