Identification

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Name
Venlafaxine
Accession Number
DB00285  (APRD00125)
Type
Small Molecule
Groups
Approved
Description

Venlafaxine (Effexor) is an antidepressant within the serotonin-norepinephrine reuptake inhibitor (SNRI) class of medications. It exerts its effects primarily by blocking the transporters involved in the reuptake of the neurotransmitters serotonin and norepinephrine, therefore leaving more active neurotransmitter in the synapse. Venlafaxine is officially approved for use in the management of major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder, and panic disorder. As of 2014, Canadian clinical practice guidelines recommend venlafaxine as a first-line option for treatment of generalized anxiety, social anxiety, panic disorder, major depressive disorder (MDD), and consider it a second-line option for management of obsessive-compulsive disorder (OCD) 9,12. Venlafaxine is also used off-label for prophylaxis of migraine headaches 10, for reduction of vasomotor symptoms associated with menopause 13, and for management of neuropathic pain (although there is only minimal evidence of efficacy for this condition) 11.

Structure
Thumb
Synonyms
  • Venlafaxina
  • Venlafaxine
  • Venlafaxinum
Product Ingredients
IngredientUNIICASInChI Key
Venlafaxine hydrochloride7D7RX5A8MO99300-78-4QYRYFNHXARDNFZ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Venlafaxine XRCapsule, extended releaseOralTEVA Canada Limited2008-02-13Not applicableCanada
Act Venlafaxine XRCapsule, extended releaseOralTEVA Canada Limited2008-02-13Not applicableCanada
Act Venlafaxine XRCapsule, extended releaseOralTEVA Canada Limited2008-02-13Not applicableCanada
EffexorTablet75 mg/1OralWyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.1993-12-012011-05-01Us
EffexorTablet75 mg/1OralPhysicians Total Care, Inc.1993-12-012011-05-31Us
EffexorTablet37.5 mg/1OralWyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.1993-12-012011-05-01Us
EffexorTablet37.5 mg/1OralPhysicians Total Care, Inc.1993-12-012011-05-31Us
EffexorTablet50 mg/1OralWyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.1993-12-012011-05-01Us
EffexorTablet25 mg/1OralWyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.1993-12-012011-05-01Us
EffexorTablet100 mg/1OralWyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.1993-12-012011-05-01Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-venlafaxine XRCapsule, extended releaseOralApotex Corporation2013-04-16Not applicableCanada
Apo-venlafaxine XRCapsule, extended releaseOralApotex Corporation2013-04-16Not applicableCanada
Apo-venlafaxine XRCapsule, extended releaseOralApotex Corporation2013-04-16Not applicableCanada
Auro-venlafaxine XRCapsule, extended releaseOralAuro Pharma Inc2016-03-14Not applicableCanada
Auro-venlafaxine XRCapsule, extended releaseOralAuro Pharma Inc2016-03-14Not applicableCanada
Auro-venlafaxine XRCapsule, extended releaseOralAuro Pharma Inc2016-03-14Not applicableCanada
Dom-venlafaxine XRCapsule, extended releaseOralDominion Pharmacal2013-05-30Not applicableCanada
Dom-venlafaxine XRCapsule, extended releaseOralDominion Pharmacal2013-05-23Not applicableCanada
Dom-venlafaxine XRCapsule, extended releaseOralDominion Pharmacal2013-05-23Not applicableCanada
EffexorTablet50 mg/1OralDirectrx2016-02-02Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Elafax
Categories
UNII
GRZ5RCB1QG
CAS number
93413-69-5
Weight
Average: 277.4018
Monoisotopic: 277.204179113
Chemical Formula
C17H27NO2
InChI Key
PNVNVHUZROJLTJ-UHFFFAOYSA-N
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
IUPAC Name
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
SMILES
COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1

Pharmacology

Indication

Venlafaxine is indicated in the management of major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder (social phobia), and panic disorder with or without agoraphobia. Venlafaxine is also used off-label for prophylaxis of migraine headaches 10, for reduction of vasomotor symptoms associated with menopause 13, and for management of neuropathic pain (although there is only minimal evidence of efficacy for this condition) 11. It is also considered a second-line option for management of obsessive-compulsive disorder (OCD) 9,12.

Associated Conditions
Pharmacodynamics

The mechanism of venlafaxine's (and its metabolite, O-desmethylvenlafaxine (ODV)) antidepressant effect is believed to be due to their potentiation of neurotransmitter activity in the central nervous system through the inhibition of the reuptake of serotonin and norepinephrine from within the synapse. Venlafaxine has also been shown to weakly inhibit dopamine reuptake. Neither venlafaxine nor ODV bind to muscarinic, histaminergic, or alpha-1 adrenergic receptorsLabel; pharmacologic activity at these receptors is hypothesized to be associated with the various anticholinergic, sedative, and cardiovascular effects seen with other psychotropic drugs. Hyponatremia has also been shown to occur as a result of treatment with SNRIs, and is associated with the development of the syndrome of inappropriate antidiuretic hormone secretion (SIADH) Label,14. Venlafaxine also demonstrates a clinically significant and dose-related effect on blood pressure, likely due to its potentiation of norepinephrine Label,15.

Mechanism of action

The exact mechanism of action of venlafaxine is unknown, but appears to be associated with the potentiation of neurotransmitter activity in the CNS. Venlafaxine and its active metabolite, O-desmethylvenlafaxine (ODV), inhibit the reuptake of both serotonin and norepinephrine with a potency greater for the 5-HT than for the NE reuptake process 16. Both venlafaxine and the ODV metabolite have weak inhibitory effects on the reuptake of dopamine but, unlike the tricyclics and similar to SSRIs, they are not active at histaminergic, muscarinic, or alpha(1)-adrenergic receptors.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
ASodium-dependent noradrenaline transporter
inhibitor
Humans
USodium-dependent dopamine transporter
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Venlafaxine is well absorbed, with at least 92% of a single dose absorbed on the basis of mass balance studies Label. Food does not affect the absorption of venlafaxine or its subsequent metabolism into ODV. Bioavailability is 45% following oral administration. Time to steady state = 3 days.

Volume of distribution
  • 7.5 ± 3.7 L/kg venlafaxine
  • 5.7 ± 1.8 L/kg [O-desmethylvenlafaxine(active metabolite)]
Protein binding

The degree of binding of venlafaxine to human plasma is 27% ± 2% at concentrations ranging from 2.5 to 2215 ng/mL. The degree of ODV binding to human plasma is 30% ± 12% at concentrations ranging from 100 to 500 ng/mL. Protein-binding-induced drug interactions with venlafaxine are not expected.

Metabolism

Undergoes extensive first pass metabolism in the liver to its major, active metabolite, O-desmethylvenlafaxine ODV, and two minor, less active metabolites, N-desmethylvenlafaxine and N,O-didesmethylvenlafaxine. Formation of ODV is catalyzed by cytochrome P450 (CYP) 2D6, whereas N-demethylation is catalyzed by CYP3A4, 2C19 and 2C9. ODV possesses antidepressant activity that is comparable to that of venlfaxine.

Route of elimination

Renal elimination of venlafaxine and its metabolites is the primary route of excretion. Approximately 87% of a venlafaxine dose is recovered in the urine within 48 hours as either unchanged venlafaxine (5%), unconjugated ODV (29%), conjugated ODV (26%), or other minor inactive metabolites (27%).

Half life

5 hours

Clearance

Steady state plasma clearance, venlafaxine = 1.3 ± 0.6 L/h/kg; Steady state plasma clearance, ODV = 0.4 ± 0.2 L/h/kg.

Toxicity

Overdose of venlafaxine is typically associated with mild symptoms. However, severe toxicity is reported with the most common symptoms being CNS depression, serotonin toxicity, seizure, or cardiac conduction abnormalities. Venlafaxine's toxicity appears to be higher than other SSRIs, with a fatal toxic dose closer to that of the tricyclic antidepressants than the SSRIs. Doses of 900 mg or more are likely to cause moderate toxicity. Deaths have been reported following large doses.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Venlafaxine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*4(A;A)A AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of venlafaxine.Details
Cytochrome P450 2D6CYP2D6*6(-;-) / (-;T)T deletion / T deletion, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of venlafaxine.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole gene deletion, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of venlafaxine.Details
Multidrug resistance protein 1---(C;C) / (C;T)C AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of remission when using venlafaxine to treat major depressive disorderDetails
Multidrug resistance protein 1---(C;C) / (C;T)T > CEffect Directly StudiedPatients with this genotype have increased risk of adverse events with venlafaxineDetails
Cytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirements, nausea, vomiting and diarrheaDetails

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinVenlafaxine may increase the antiplatelet activities of (R)-warfarin.
(S)-WarfarinVenlafaxine may increase the antiplatelet activities of (S)-Warfarin.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Venlafaxine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Venlafaxine is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Venlafaxine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Venlafaxine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamineVenlafaxine may increase the tachycardic activities of 4-Bromo-2,5-dimethoxyphenethylamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Venlafaxine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Take with food.

References

Synthesis Reference

Thomas P. Jerussi, Chrisantha H. Senanayake, "Derivatives of (+)-venlafaxine and methods of preparing and using the same." U.S. Patent US6197828, issued June, 1994.

US6197828
General References
  1. Golden RN, Nicholas L: Antidepressant efficacy of venlafaxine. Depress Anxiety. 2000;12 Suppl 1:45-9. [PubMed:11098413]
  2. Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. [PubMed:16974189]
  3. Bielski RJ, Ventura D, Chang CC: A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder. J Clin Psychiatry. 2004 Sep;65(9):1190-6. [PubMed:15367045]
  4. Rowbotham MC, Goli V, Kunz NR, Lei D: Venlafaxine extended release in the treatment of painful diabetic neuropathy: a double-blind, placebo-controlled study. Pain. 2004 Aug;110(3):697-706. [PubMed:15288411]
  5. Ozyalcin SN, Talu GK, Kiziltan E, Yucel B, Ertas M, Disci R: The efficacy and safety of venlafaxine in the prophylaxis of migraine. Headache. 2005 Feb;45(2):144-52. [PubMed:15705120]
  6. Whirl-Carrillo M, McDonagh EM, Hebert JM, Gong L, Sangkuhl K, Thorn CF, Altman RB, Klein TE: Pharmacogenomics knowledge for personalized medicine. Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96. [PubMed:22992668]
  7. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  8. Shelton RC: Serotonin and Norepinephrine Reuptake Inhibitors. Handb Exp Pharmacol. 2019 Mar 6. doi: 10.1007/164_2018_164. [PubMed:30838456]
  9. Kennedy SH, Lam RW, McIntyre RS, Tourjman SV, Bhat V, Blier P, Hasnain M, Jollant F, Levitt AJ, MacQueen GM, McInerney SJ, McIntosh D, Milev RV, Muller DJ, Parikh SV, Pearson NL, Ravindran AV, Uher R: Canadian Network for Mood and Anxiety Treatments (CANMAT) 2016 Clinical Guidelines for the Management of Adults with Major Depressive Disorder: Section 3. Pharmacological Treatments. Can J Psychiatry. 2016 Sep;61(9):540-60. doi: 10.1177/0706743716659417. Epub 2016 Aug 2. [PubMed:27486148]
  10. Pringsheim T, Davenport W, Mackie G, Worthington I, Aube M, Christie SN, Gladstone J, Becker WJ: Canadian Headache Society guideline for migraine prophylaxis. Can J Neurol Sci. 2012 Mar;39(2 Suppl 2):S1-59. [PubMed:22683887]
  11. Gallagher HC, Gallagher RM, Butler M, Buggy DJ, Henman MC: Venlafaxine for neuropathic pain in adults. Cochrane Database Syst Rev. 2015 Aug 23;(8):CD011091. doi: 10.1002/14651858.CD011091.pub2. [PubMed:26298465]
  12. Katzman MA, Bleau P, Blier P, Chokka P, Kjernisted K, Van Ameringen M, Antony MM, Bouchard S, Brunet A, Flament M, Grigoriadis S, Mendlowitz S, O'Connor K, Rabheru K, Richter PM, Robichaud M, Walker JR: Canadian clinical practice guidelines for the management of anxiety, posttraumatic stress and obsessive-compulsive disorders. BMC Psychiatry. 2014;14 Suppl 1:S1. doi: 10.1186/1471-244X-14-S1-S1. Epub 2014 Jul 2. [PubMed:25081580]
  13. Handley AP, Williams M: The efficacy and tolerability of SSRI/SNRIs in the treatment of vasomotor symptoms in menopausal women: a systematic review. J Am Assoc Nurse Pract. 2015 Jan;27(1):54-61. doi: 10.1002/2327-6924.12137. Epub 2014 Jun 19. [PubMed:24944075]
  14. Roxanas M, Hibbert E, Field M: Venlafaxine hyponatraemia: incidence, mechanism and management. Aust N Z J Psychiatry. 2007 May;41(5):411-8. doi: 10.1080/00048670701261202. [PubMed:17464733]
  15. Thase ME: Effects of venlafaxine on blood pressure: a meta-analysis of original data from 3744 depressed patients. J Clin Psychiatry. 1998 Oct;59(10):502-8. [PubMed:9818630]
  16. Bymaster FP, Dreshfield-Ahmad LJ, Threlkeld PG, Shaw JL, Thompson L, Nelson DL, Hemrick-Luecke SK, Wong DT: Comparative affinity of duloxetine and venlafaxine for serotonin and norepinephrine transporters in vitro and in vivo, human serotonin receptor subtypes, and other neuronal receptors. Neuropsychopharmacology. 2001 Dec;25(6):871-80. [PubMed:11750180]
External Links
Human Metabolome Database
HMDB0061166
KEGG Drug
D08670
KEGG Compound
C07187
PubChem Compound
5656
PubChem Substance
46504593
ChemSpider
5454
BindingDB
82071
ChEBI
9943
ChEMBL
CHEMBL637
Therapeutic Targets Database
DAP000054
PharmGKB
PA451866
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Venlafaxine
ATC Codes
N06AX16 — Venlafaxine
AHFS Codes
  • 28:16.04.16 — Selective Serotonin and Norepinephrine-reuptake Inhibitors
FDA label
Download (3.38 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers9
1CompletedBasic ScienceBypass, Gastric / Post-gastrointestinal bypass surgery / Roux-en-Y Gastric Bypass1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers3
1RecruitingPreventionAlzheimer's Disease (AD)1
1, 2CompletedTreatmentDepression / Major Depressive Disorder (MDD)2
1, 2CompletedTreatmentFibromyalgia1
1, 2CompletedTreatmentMajor Depressive Disorder (MDD) / Partner Relational Disorder (V61.10)1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
2CompletedPreventionCervical Pain1
2CompletedTreatmentBipolar Disorder (BD) / Depressive Disorders1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentDepression / Major Depressive Disorder (MDD)1
2CompletedTreatmentDepression / Marijuana Abuse1
2CompletedTreatmentDepressive Disorders1
2CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
2CompletedTreatmentMajor Depressive Disorder (MDD)3
2CompletedTreatmentPost-traumatic Neuropathic Pain1
2TerminatedTreatmentAnxiety Disorders1
2TerminatedTreatmentDepression1
2TerminatedTreatmentMajor Depressive Disorder (MDD)1
2TerminatedTreatmentProstate Cancer1
2, 3CompletedTreatmentAlcohol-Related Disorders / Anxiety Disorders1
2, 3CompletedTreatmentDepression1
2, 3CompletedTreatmentDepression / Suicide, Attempted1
2, 3Unknown StatusTreatmentMajor Depressive Disorder (MDD)1
3CompletedPreventionDepression1
3CompletedSupportive CareBone Mineral Density Quantitative Trait Locus 71
3CompletedSupportive CareMenopausal Hot Flushes1
3CompletedTreatmentAdenocarcinoma, Prostate1
3CompletedTreatmentAnxiety1
3CompletedTreatmentAnxiety Disorders2
3CompletedTreatmentDepression3
3CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD) / Moods Disorders / Psychiatric Disorder NOS1
3CompletedTreatmentDepression / Parkinson's Disease (PD)1
3CompletedTreatmentDepressive Disorder, Treatment-Resistant / Major depressive disorder, recurrent episode2
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentMajor Depressive Disorder (MDD)8
3CompletedTreatmentMajor Depressive Disorder (MDD) / Sleeplessness1
3CompletedTreatmentMajor Depressive Disorder (MDD) / Treatment Resistant Depression (TRD)1
3CompletedTreatmentMajor depressive disorder, recurrent episode3
3CompletedTreatmentObsessive Compulsive Disorder (OCD)1
3CompletedTreatmentPanic Disorders3
3CompletedTreatmentSocial Anxiety Disorder (SAD)1
3RecruitingTreatmentDepressive Disorder, Treatment-Resistant1
3RecruitingTreatmentMajor Depressive Disorder (MDD)1
3TerminatedSupportive CareMenopausal Hot Flushes / Prostate Cancer1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
4Active Not RecruitingBasic ScienceMajor Depressive Disorder (MDD)1
4Active Not RecruitingTreatmentObstructive Sleep Apnea (OSA)1
4CompletedNot AvailableDepression1
4CompletedNot AvailableRoux En Y Gastric Bypass / Sleeve Gastrectomy1
4CompletedBasic ScienceDepression1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedTreatmentAnxiety Disorders1
4CompletedTreatmentAnxiety Disorders / Depression1
4CompletedTreatmentBack Pain / Depression1
4CompletedTreatmentBipolar Disorder (BD)2
4CompletedTreatmentBipolar Disorder (BD) / Depression1
4CompletedTreatmentBipolar Disorder (BD) / Depression / Depressive Disorders1
4CompletedTreatmentBipolar Type II Disorder1
4CompletedTreatmentDementias / Depression1
4CompletedTreatmentDepression9
4CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD) / Unipolar Depression1
4CompletedTreatmentDepression / Mild Cognitive Impairment (MCI)1
4CompletedTreatmentDepression / Post Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentDysthymic Disorder / Major Depressive Disorder (MDD) / Spinal Cord Injuries (SCI)1
4CompletedTreatmentMajor Depressive Disorder (MDD)10
4CompletedTreatmentMajor Depressive Disorder (MDD) / Recurrences1
4CompletedTreatmentOsteoarthritis (OA) / Pain NOS1
4CompletedTreatmentSocial Phobia1
4CompletedTreatmentTraumatic Brain Injury (TBI)1
4CompletedTreatmentVestibular Migraine1
4RecruitingNot AvailableDepressive Disorders / Lactation1
4RecruitingDiagnosticAsthma Bronchial / Asthma: [Nos] or [Attack] / Major Depressive Disorder (MDD)1
4RecruitingDiagnosticSevere Major Depression Disorder1
4RecruitingHealth Services ResearchMajor Depressive Disorder (MDD)1
4RecruitingTreatmentMajor Depressive Disorder (MDD) / Major Depressive Episode1
4RecruitingTreatmentTreatment Resistant Major Depressive Disorder / Treatment Resistant Major Depressive Disorder Depression1
4TerminatedPreventionDepression1
4TerminatedTreatmentDepression / Relapsing Remitting Multiple Sclerosis (RRMS)1
4TerminatedTreatmentMajor Depressive Disorder (MDD)1
4Unknown StatusNot AvailableMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentAntidepressive Agents / Fluoxetine / Major Depressive Disorder (MDD) / Pharmacogenetics / Venlafaxine1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)2
4WithdrawnTreatmentMajor Depressive Disorder (MDD)1
4WithdrawnTreatmentPosttraumatic Stress Disorders1
Not AvailableActive Not RecruitingNot AvailableAnxiety Disorders / Generalized Anxiety Disorder (GAD) / Obsessive Compulsive Disorder (OCD) / Panic Disorders / Post Traumatic Stress Disorder (PTSD) / Social Anxiety Disorder (SAD)1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast / Depression / Menopausal Hot Flushes / Psychosocial Effects of Cancer and Its Treatment1
Not AvailableActive Not RecruitingNot AvailableDepression/Depressed State1
Not AvailableActive Not RecruitingNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingTreatmentAnxiety / Depression / Mild Cognitive Impairment (MCI)1
Not AvailableActive Not RecruitingTreatmentDepression1
Not AvailableCompletedNot AvailableAcute Kidney Injury (AKI) / Depression1
Not AvailableCompletedNot AvailableDepression / Depressive Disorders / Inflammatory Reaction1
Not AvailableCompletedBasic ScienceMajor Depressive Disorder (MDD)2
Not AvailableCompletedSupportive CareCancer, Breast / Menopausal Hot Flushes / Sleep disorders and disturbances1
Not AvailableCompletedSupportive CarePeripheral neuropathy1
Not AvailableCompletedTreatmentAlzheimer's Disease (AD) / Depression1
Not AvailableCompletedTreatmentDepression / Depressive Disorders1
Not AvailableCompletedTreatmentIndigestion1
Not AvailableCompletedTreatmentMajor Depressive Disorder (MDD)1
Not AvailableCompletedTreatmentMenopausal Hot Flushes / Menopause / Vasomotor Disturbance1
Not AvailableCompletedTreatmentPain NOS / Pain, Neuropathic / Spinal Cord Injuries (SCI)1
Not AvailableCompletedTreatmentSpinal Cord Injuries (SCI)1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingSupportive CareStage III Cutaneous Squamous Cell Carcinoma of the Head and Neck AJCC v8 / Stage IV Cutaneous Squamous Cell Carcinoma of the Head and Neck AJCC v81
Not AvailableRecruitingTreatmentAlcohol-Related Disorders / Brain Injury / Depression / Disease, Chronic / Mild Cognitive Impairment (MCI) / Pain NOS / Posttraumatic Stress Disorders / Quality of Life / Substance-Related Disorders / Suicidal Thoughts / Wounds and Injuries1
Not AvailableUnknown StatusNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)1
Not AvailableWithdrawnSupportive CareMenopausal Hot Flushes1

Pharmacoeconomics

Manufacturers
  • Wyeth pharmaceuticals inc
  • Teva pharmaceuticals usa inc
  • Osmotica pharmaceutical corp
  • Actavis totowa llc
  • Amneal pharmaceuticals
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Dr reddys laboratories ltd
  • Mylan pharmaceuticals inc
  • Pliva hrvatska doo
  • Sandoz inc
  • Vintage pharmaceuticals llc
  • Zydus pharmaceuticals usa inc
  • Wyeth
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Cadila Healthcare Ltd.
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Caremark LLC
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Schwarz Pharma Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Upstate Pharma LLC
  • Vangard Labs Inc.
  • Wyeth Pharmaceuticals
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral75 mg/1
TabletOral
Capsule, extended releaseOral150 mg
Capsule, extended releaseOral37.5 mg
Capsule, extended releaseOral75 mg
Capsule, extended releaseOral150 mg/1
Capsule, extended releaseOral37.5 mg/1
Capsule, extended releaseOral75 mg/1
Capsule, extended releaseOral
Tablet, coatedOral150 mg/1
Tablet, coatedOral225 mg/1
Tablet, coatedOral75 mg/1
Tablet, extended releaseOral150 mg/1
Tablet, extended releaseOral225 mg/1
Tablet, extended releaseOral37.5 mg/1
Tablet, extended releaseOral75 mg/1
Capsule, coated, extended releaseOral75 mg/1
Capsule, delayed releaseOral75 mg/1
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral37.5 mg/1
TabletOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral37.5 mg/1
Tablet, film coatedOral50 mg/1
Tablet, film coatedOral75 mg/1
Tablet, film coated, extended releaseOral150 mg/1
Tablet, film coated, extended releaseOral225 mg/1
Tablet, film coated, extended releaseOral37.5 mg/1
Tablet, film coated, extended releaseOral75 mg/1
Prices
Unit descriptionCostUnit
Venlafaxine HCl 30 225 mg 24 Hour tablet Bottle276.98USD bottle
Effexor XR 30 37.5 mg 24 Hour Capsule Bottle144.33USD bottle
Venlafaxine HCl 30 37.5 mg 24 Hour tablet Bottle114.46USD bottle
Effexor 30 75 mg tablet Bottle87.83USD bottle
Effexor 30 25 mg tablet Bottle74.82USD bottle
Effexor XR 150 mg 24 Hour Capsule5.87USD capsule
Effexor xr 150 mg capsule5.65USD capsule
Effexor XR 75 mg 24 Hour Capsule5.39USD capsule
Effexor xr 75 mg capsule4.76USD capsule
Venlafaxine HCl 150 mg 24 Hour tablet4.72USD tablet
Effexor xr 37.5 mg capsule4.63USD capsule
Venlafaxine HCl 75 mg 24 Hour tablet4.42USD tablet
Effexor 100 mg tablet2.92USD tablet
Effexor 75 mg tablet2.7USD tablet
Effexor 50 mg tablet2.6USD tablet
Effexor 37.5 mg tablet2.5USD tablet
Effexor 25 mg tablet2.4USD tablet
Venlafaxine hcl 100 mg tablet2.36USD tablet
Venlafaxine hcl 75 mg tablet2.23USD tablet
Effexor Xr 150 mg Extended-Release Capsule2.16USD capsule
Venlafaxine hcl 50 mg tablet2.1USD tablet
Effexor Xr 75 mg Extended-Release Capsule2.05USD capsule
Venlafaxine hcl 37.5 mg tablet2.04USD tablet
Venlafaxine hcl 25 mg tablet1.98USD tablet
Apo-Venlafaxine Xr 150 mg Extended-Release Capsule1.2USD capsule
Co Venlafaxine Xr 150 mg Extended-Release Capsule1.2USD capsule
Mylan-Venlafaxine Xr 150 mg Extended-Release Capsule1.2USD capsule
Novo-Venlafaxine Xr 150 mg Extended-Release Capsule1.2USD capsule
Pms-Venlafaxine Xr 150 mg Extended-Release Capsule1.2USD capsule
Ratio-Venlafaxine Xr 150 mg Extended-Release Capsule1.2USD capsule
Sandoz Venlafaxine Xr 150 mg Extended-Release Capsule1.2USD capsule
Apo-Venlafaxine Xr 75 mg Extended-Release Capsule1.14USD capsule
Co Venlafaxine Xr 75 mg Extended-Release Capsule1.14USD capsule
Mylan-Venlafaxine Xr 75 mg Extended-Release Capsule1.14USD capsule
Novo-Venlafaxine Xr 75 mg Extended-Release Capsule1.14USD capsule
Pms-Venlafaxine Xr 75 mg Extended-Release Capsule1.14USD capsule
Ratio-Venlafaxine Xr 75 mg Extended-Release Capsule1.14USD capsule
Sandoz Venlafaxine Xr 75 mg Extended-Release Capsule1.14USD capsule
Effexor Xr 37.5 mg Extended-Release Capsule1.02USD capsule
Apo-Venlafaxine Xr 37.5 mg Extended-Release Capsule0.57USD capsule
Co Venlafaxine Xr 37.5 mg Extended-Release Capsule0.57USD capsule
Mylan-Venlafaxine Xr 37.5 mg Extended-Release Capsule0.57USD capsule
Novo-Venlafaxine Xr 37.5 mg Extended-Release Capsule0.57USD capsule
Pms-Venlafaxine Xr 37.5 mg Extended-Release Capsule0.57USD capsule
Ratio-Venlafaxine Xr 37.5 mg Extended-Release Capsule0.57USD capsule
Sandoz Venlafaxine Xr 37.5 mg Extended-Release Capsule0.57USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5916923No1999-06-292013-06-28Us
CA2126305No2006-10-172014-06-20Canada
CA2199778No2005-12-202017-03-12Canada
US6403120Yes2002-06-112017-09-20Us
US6419958Yes2002-07-162017-09-20Us
US6274171Yes2001-08-142017-09-20Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)215-217 °C (Hydrochloride salt)Not Available
water solubility572 mg/ml (Hydrochloride salt)Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 mg/mLALOGPS
logP2.69ALOGPS
logP2.74ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.02 m3·mol-1ChemAxon
Polarizability32.33 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9782
Blood Brain Barrier+0.9382
Caco-2 permeable+0.852
P-glycoprotein substrateSubstrate0.6534
P-glycoprotein inhibitor IInhibitor0.7031
P-glycoprotein inhibitor IIInhibitor0.8031
Renal organic cation transporterNon-inhibitor0.5792
CYP450 2C9 substrateNon-substrate0.7583
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.7664
CYP450 2C9 inhibitorNon-inhibitor0.6876
CYP450 2D6 inhibitorInhibitor0.7287
CYP450 2C19 inhibitorNon-inhibitor0.7199
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8666
Ames testNon AMES toxic0.8
CarcinogenicityNon-carcinogens0.6762
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.5404 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5486
hERG inhibition (predictor II)Inhibitor0.6627
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-d413fb5f16658fcc5acb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-182f1032c3f72220679d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dj-0910000000-c7a4a25a9bc95faa6db1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-7be3d65db3af35be404e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-615322444dcf11a7fb8d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0090000000-d212108d9a8267ed7dad
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-0c4e12d13e69311b26bf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0bvi-4090000000-8bf2805a95084bfd952a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9520000000-de599153aa118f97ad81
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-8900000000-6e9f54b654899b486e4d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-9800000000-d762b2d7edeba1e12b28
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-9700000000-2b8ebcefcf1274550d32
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-c592b4ae2ead9b2bb7ea
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0bvi-4090000000-30b9b5dca017215ebaa4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9620000000-ab905f15470a13b750c5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-8900000000-52ec7a86d35dbbd47681
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-9800000000-7a7cc5b11e1a30499063
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-9700000000-062f05f9fe2a1540985c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0090000000-8eb971c1dc9a14696c31
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01t9-2090000000-af607e34f7f6700231a4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9140000000-0b22aeda0f56bf825768
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9300000000-f28ae1a2451e218836c6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9400000000-c36a2f70d6d9fd69dbfe
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9500000000-43a71bea54c5b09c4c9a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9400000000-9763935e9812b45adddb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0bvi-6090000000-fabb5e8a0fd59b8420ca
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9100000000-b67e5a7dbbd83cf2a7a7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9200000000-2300decf19900a1b84e4
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0090000000-40f0dac6b8ca62d0314f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01t9-0390000000-7a760936fedd0f48cebf
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9260000000-0b8e3be9620e0271d683
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01t9-2090000000-94fb4781a9910b6b1932
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9140000000-e2c800f5f39f048c545a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9400000000-e0fa4c4197355be8d0fa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9500000000-23cbb70f5d3c368966bb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9500000000-998e2271dd7ac0572d54
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Cyclohexanols / Aralkylamines / Alkyl aryl ethers / Tertiary alcohols / 1,3-aminoalcohols / Trialkylamines / Cyclic alcohols and derivatives / Organopnictogen compounds
show 1 more
Substituents
Phenoxy compound / Anisole / Methoxybenzene / Alkyl aryl ether / Aralkylamine / Cyclohexanol / Monocyclic benzene moiety / 1,3-aminoalcohol / Tertiary alcohol / Cyclic alcohol
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary alcohol, tertiary amino compound, monomethoxybenzene, cyclohexanols (CHEBI:9943)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
K(i)=82nM
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Chen F, Larsen MB, Sanchez C, Wiborg O: The S-enantiomer of R,S-citalopram, increases inhibitor binding to the human serotonin transporter by an allosteric mechanism. Comparison with other serotonin transporter inhibitors. Eur Neuropsychopharmacol. 2005 Mar;15(2):193-8. [PubMed:15695064]
  2. Gould GG, Altamirano AV, Javors MA, Frazer A: A comparison of the chronic treatment effects of venlafaxine and other antidepressants on serotonin and norepinephrine transporters. Biol Psychiatry. 2006 Mar 1;59(5):408-14. Epub 2005 Sep 2. [PubMed:16140280]
  3. Shang Y, Gibbs MA, Marek GJ, Stiger T, Burstein AH, Marek K, Seibyl JP, Rogers JF: Displacement of serotonin and dopamine transporters by venlafaxine extended release capsule at steady state: a [123I]2beta-carbomethoxy-3beta-(4-iodophenyl)-tropane single photon emission computed tomography imaging study. J Clin Psychopharmacol. 2007 Feb;27(1):71-5. [PubMed:17224717]
  4. Malizia AL, Melichar JM, Brown DJ, Gunn RN, Reynolds A, Jones T, Nutt DJ: Demonstration of clomipramine and venlafaxine occupation at serotonin reuptake sites in man in vivo. J Psychopharmacol. 1997;11(3):279-81. [PubMed:9305421]
  5. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
  6. Van Ameringen M, Mancini C, Patterson B, Simpson W: Pharmacotherapy for social anxiety disorder: an update. Isr J Psychiatry Relat Sci. 2009;46(1):53-61. [PubMed:19728573]
  7. Beique J, de Montigny C, Blier P, Debonnel G: Effects of sustained administration of the serotonin and norepinephrine reuptake inhibitor venlafaxine: I. in vivo electrophysiological studies in the rat. Neuropharmacology. 2000 Jul 24;39(10):1800-12. [PubMed:10884561]
  8. Westenberg HG: Recent advances in understanding and treating social anxiety disorder. CNS Spectr. 2009 Feb;14(2 Suppl 3):24-33. [PubMed:19238127]
  9. Sindrup SH, Otto M, Finnerup NB, Jensen TS: Antidepressants in the treatment of neuropathic pain. Basic Clin Pharmacol Toxicol. 2005 Jun;96(6):399-409. [PubMed:15910402]
  10. Bymaster FP, Dreshfield-Ahmad LJ, Threlkeld PG, Shaw JL, Thompson L, Nelson DL, Hemrick-Luecke SK, Wong DT: Comparative affinity of duloxetine and venlafaxine for serotonin and norepinephrine transporters in vitro and in vivo, human serotonin receptor subtypes, and other neuronal receptors. Neuropsychopharmacology. 2001 Dec;25(6):871-80. [PubMed:11750180]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
K(i)=2480nM
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Vaishnavi SN, Nemeroff CB, Plott SJ, Rao SG, Kranzler J, Owens MJ: Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55(3):320-2. [PubMed:14744476]
  2. Mitchell HA, Ahern TH, Liles LC, Javors MA, Weinshenker D: The effects of norepinephrine transporter inactivation on locomotor activity in mice. Biol Psychiatry. 2006 Nov 15;60(10):1046-52. Epub 2006 Aug 7. [PubMed:16893531]
  3. Beique JC, Lavoie N, de Montigny C, Debonnel G: Affinities of venlafaxine and various reuptake inhibitors for the serotonin and norepinephrine transporters. Eur J Pharmacol. 1998 May 15;349(1):129-32. [PubMed:9669506]
  4. Van Ameringen M, Mancini C, Patterson B, Simpson W: Pharmacotherapy for social anxiety disorder: an update. Isr J Psychiatry Relat Sci. 2009;46(1):53-61. [PubMed:19728573]
  5. Beique J, de Montigny C, Blier P, Debonnel G: Effects of sustained administration of the serotonin and norepinephrine reuptake inhibitor venlafaxine: I. in vivo electrophysiological studies in the rat. Neuropharmacology. 2000 Jul 24;39(10):1800-12. [PubMed:10884561]
  6. Westenberg HG: Recent advances in understanding and treating social anxiety disorder. CNS Spectr. 2009 Feb;14(2 Suppl 3):24-33. [PubMed:19238127]
  7. Sindrup SH, Otto M, Finnerup NB, Jensen TS: Antidepressants in the treatment of neuropathic pain. Basic Clin Pharmacol Toxicol. 2005 Jun;96(6):399-409. [PubMed:15910402]
  8. Bymaster FP, Dreshfield-Ahmad LJ, Threlkeld PG, Shaw JL, Thompson L, Nelson DL, Hemrick-Luecke SK, Wong DT: Comparative affinity of duloxetine and venlafaxine for serotonin and norepinephrine transporters in vitro and in vivo, human serotonin receptor subtypes, and other neuronal receptors. Neuropsychopharmacology. 2001 Dec;25(6):871-80. [PubMed:11750180]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Dawson LA, Nguyen HQ, Geiger A: Effects of venlafaxine on extracellular concentrations of 5-HT and noradrenaline in the rat frontal cortex: augmentation via 5-HT1A receptor antagonism. Neuropharmacology. 1999 Aug;38(8):1153-63. [PubMed:10462128]
  2. Bourin M: [Psychopharmacological profile of venlafaxine]. Encephale. 1999 Jun;25 Spec No 2:21-2; discussion 23-5. [PubMed:10434156]
  3. Barkin RL, Fawcett J: The management challenges of chronic pain: the role of antidepressants. Am J Ther. 2000 Jan;7(1):31-47. [PubMed:11319571]
  4. Lemke MR: [Antidepressant effects of dopamine agonists. Experimental and clinical findings]. Nervenarzt. 2007 Jan;78(1):31-8. [PubMed:17187269]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Fogelman SM, Schmider J, Venkatakrishnan K, von Moltke LL, Harmatz JS, Shader RI, Greenblatt DJ: O- and N-demethylation of venlafaxine in vitro by human liver microsomes and by microsomes from cDNA-transfected cells: effect of metabolic inhibitors and SSRI antidepressants. Neuropsychopharmacology. 1999 May;20(5):480-90. [PubMed:10192828]
  2. Lin XQ, Wang P, Cai WK, Xu GL, Yang M, Zhou MD, Sun M, He F, He GH: The Associations Between CYP2D6 Metabolizer Status and Pharmacokinetics and Clinical Outcomes of Venlafaxine: A Systematic Review and Meta-Analysis. Pharmacopsychiatry. 2018 Nov 28. doi: 10.1055/a-0792-1340. [PubMed:30485867]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Otton SV, Ball SE, Cheung SW, Inaba T, Rudolph RL, Sellers EM: Venlafaxine oxidation in vitro is catalysed by CYP2D6. Br J Clin Pharmacol. 1996 Feb;41(2):149-56. [PubMed:8838442]
  3. Ciusani E, Zullino DF, Eap CB, Brawand-Amey M, Brocard M, Baumann P: Combination therapy with venlafaxine and carbamazepine in depressive patients not responding to venlafaxine: pharmacokinetic and clinical aspects. J Psychopharmacol. 2004 Dec;18(4):559-66. doi: 10.1177/026988110401800414. [PubMed:15582923]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [PubMed:12649369]
  2. Uhr M, Grauer MT, Holsboer F: Differential enhancement of antidepressant penetration into the brain in mice with abcb1ab (mdr1ab) P-glycoprotein gene disruption. Biol Psychiatry. 2003 Oct 15;54(8):840-6. [PubMed:14550684]
  3. Karlsson L, Schmitt U, Josefsson M, Carlsson B, Ahlner J, Bengtsson F, Kugelberg FC, Hiemke C: Blood-brain barrier penetration of the enantiomers of venlafaxine and its metabolites in mice lacking P-glycoprotein. Eur Neuropsychopharmacol. 2010 Sep;20(9):632-40. doi: 10.1016/j.euroneuro.2010.04.004. Epub 2010 May 13. [PubMed:20466523]
  4. Bachmeier CJ, Beaulieu-Abdelahad D, Ganey NJ, Mullan MJ, Levin GM: Induction of drug efflux protein expression by venlafaxine but not desvenlafaxine. Biopharm Drug Dispos. 2011 May;32(4):233-44. doi: 10.1002/bdd.753. Epub 2011 Mar 28. [PubMed:21446053]
  5. Zhou Y, Zhang G, Rao Z, Yang Y, Zhou Q, Qin H, Wei Y, Wu X: Increased brain uptake of venlafaxine loaded solid lipid nanoparticles by overcoming the efflux function and expression of P-gp. Arch Pharm Res. 2015 Jul;38(7):1325-35. doi: 10.1007/s12272-014-0539-6. Epub 2015 Jan 8. [PubMed:25567760]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Bachmeier CJ, Beaulieu-Abdelahad D, Ganey NJ, Mullan MJ, Levin GM: Induction of drug efflux protein expression by venlafaxine but not desvenlafaxine. Biopharm Drug Dispos. 2011 May;32(4):233-44. doi: 10.1002/bdd.753. Epub 2011 Mar 28. [PubMed:21446053]

Drug created on June 13, 2005 07:24 / Updated on October 15, 2019 18:53