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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- 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
Structure for Venlafaxine (DB00285)
- Synonyms
- Venlafaxina
- Venlafaxine
- Venlafaxinum
- Product Ingredients
Ingredient UNII CAS InChI Key Venlafaxine hydrochloride 7D7RX5A8MO 99300-78-4 QYRYFNHXARDNFZ-UHFFFAOYSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAct Venlafaxine XR Capsule, extended release Oral TEVA Canada Limited 2008-02-13 Not applicable Canada 
Act Venlafaxine XR Capsule, extended release Oral TEVA Canada Limited 2008-02-13 Not applicable Canada Act Venlafaxine XR Capsule, extended release Oral TEVA Canada Limited 2008-02-13 Not applicable Canada Effexor Tablet 75 mg/1 Oral Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc. 1993-12-01 2011-05-01 US 
Effexor Tablet 37.5 mg/1 Oral Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc. 1993-12-01 2011-05-01 US Effexor Tablet 50 mg/1 Oral Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc. 1993-12-01 2011-05-01 US Effexor Tablet 25 mg/1 Oral Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc. 1993-12-01 2011-05-01 US Effexor Tablet 75 mg/1 Oral Physicians Total Care, Inc. 1993-12-01 2011-05-31 US Effexor Tablet 37.5 mg/1 Oral Physicians Total Care, Inc. 1993-12-01 2011-05-31 US Effexor Tablet 100 mg/1 Oral Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc. 1993-12-01 2011-05-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataApo-venlafaxine XR Capsule, extended release Oral Apotex Corporation 2013-04-16 Not applicable Canada Apo-venlafaxine XR Capsule, extended release Oral Apotex Corporation 2013-04-16 Not applicable Canada Apo-venlafaxine XR Capsule, extended release Oral Apotex Corporation 2013-04-16 Not applicable Canada Auro-venlafaxine XR Capsule, extended release Oral Auro Pharma Inc 2016-03-14 Not applicable Canada Auro-venlafaxine XR Capsule, extended release Oral Auro Pharma Inc 2016-03-14 Not applicable Canada Auro-venlafaxine XR Capsule, extended release Oral Auro Pharma Inc 2016-03-14 Not applicable Canada Dom-venlafaxine XR Capsule, extended release Oral Dominion Pharmacal 2013-05-30 Not applicable Canada Dom-venlafaxine XR Capsule, extended release Oral Dominion Pharmacal 2013-05-23 Not applicable Canada Dom-venlafaxine XR Capsule, extended release Oral Dominion Pharmacal 2013-05-23 Not applicable Canada Effexor Tablet 50 mg/1 Oral Direct Rx 2016-02-02 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- International/Other Brands
- Elafax
- Categories
- Agents producing tachycardia
- Agents that reduce seizure threshold
- Alcohols
- Amines
- Antidepressive Agents
- Antidepressive Agents, Second-Generation
- BCRP/ABCG2 Inducers
- Central Nervous System Agents
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cyclohexanes
- Cyclohexanols
- Cycloparaffins
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Ethylamines
- Fatty Alcohols
- Hexanols
- Hypoglycemia-Associated Agents
- Lipids
- Membrane Transport Modulators
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Norepinephrine Uptake Inhibitors
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Phenethylamines
- Potential QTc-Prolonging Agents
- Psychoanaleptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin and Noradrenaline Reuptake Inhibitors
- Serotonin Modulators
- 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.
Target Actions Organism ASodium-dependent serotonin transporter inhibitorHumans ASodium-dependent noradrenaline transporter inhibitorHumans USodium-dependent dopamine transporter inhibitorHumans - 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
Pathway Category Venlafaxine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*4 (A;A) A Allele Effect Directly Studied Patients with this genotype have reduced metabolism of venlafaxine. Details Cytochrome P450 2D6 CYP2D6*6 (-;T) / (-;-) T deletion / T deletion, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of venlafaxine. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole gene deletion, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of venlafaxine. Details Multidrug resistance protein 1 --- (C;C) / (C;T) C Allele Effect Directly Studied Patients with this genotype have an increased likelihood of remission when using venlafaxine to treat major depressive disorder Details Multidrug resistance protein 1 --- (C;C) / (C;T) T > C Effect Directly Studied Patients with this genotype have increased risk of adverse events with venlafaxine Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements, nausea, vomiting and diarrhea Details
Unlock Additional Data
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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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.
Learn more 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.
Learn moreInteractions
- 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.
Drug Interaction Unlock Additional Data(R)-warfarin Venlafaxine may increase the antiplatelet activities of (R)-warfarin. (S)-Warfarin Venlafaxine may increase the antiplatelet activities of (S)-Warfarin. 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine The metabolism of Venlafaxine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine. 2,4-thiazolidinedione The risk or severity of hypoglycemia can be increased when Venlafaxine is combined with 2,4-thiazolidinedione. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of serotonin syndrome can be increased when Venlafaxine is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Venlafaxine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when Venlafaxine is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-Bromo-2,5-dimethoxyphenethylamine Venlafaxine may increase the tachycardic activities of 4-Bromo-2,5-dimethoxyphenethylamine. 4-hydroxycoumarin Venlafaxine may increase the antiplatelet activities of 4-hydroxycoumarin. 4-Methoxyamphetamine The metabolism of 4-Methoxyamphetamine can be decreased when combined with Venlafaxine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Avoid alcohol. Prescribing information recommends the avoidance of alcohol during therapy.
- Avoid St. John's Wort. Co-administration of St. John's Wort may lead to additive serotonergic activity and an increased risk of serotonin syndrome.
- Take with food. Co-administration with food helps to alleviate/mitigate GI upset.
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
- Golden RN, Nicholas L: Antidepressant efficacy of venlafaxine. Depress Anxiety. 2000;12 Suppl 1:45-9. [PubMed:11098413]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Shelton RC: Serotonin and Norepinephrine Reuptake Inhibitors. Handb Exp Pharmacol. 2019 Mar 6. doi: 10.1007/164_2018_164. [PubMed:30838456]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: Effexor XR® extended-release capsules [Link]
- FDA Approved Drug Products: Venlafaxine oral tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0061166
- KEGG Drug
- D08670
- KEGG Compound
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- Venlafaxine
- ATC Codes
- N06AX16 — Venlafaxine
- AHFS Codes
- 28:16.04.16 — Selective Serotonin and Norepinephrine-reuptake Inhibitors
Clinical Trials
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- Dosage forms
Form Route Strength Tablet Oral 75 mg/1 Tablet Oral Capsule, extended release Oral 150 mg Capsule, extended release Oral 37.5 mg Capsule, extended release Oral 75 mg Capsule, extended release Oral 150 mg/1 Capsule, extended release Oral 37.5 mg/1 Capsule, extended release Oral 75 mg/1 Capsule, extended release Oral Tablet, coated Oral 150 mg/1 Tablet, coated Oral 225 mg/1 Tablet, coated Oral 75 mg/1 Tablet, extended release Oral 150 mg/1 Tablet, extended release Oral 225 mg/1 Tablet, extended release Oral 37.5 mg/1 Tablet, extended release Oral 75 mg/1 Capsule, coated, extended release Oral 75 mg/1 Capsule, delayed release Oral 75 mg/1 Tablet Oral 100 mg/1 Tablet Oral 150 mg/1 Tablet Oral 225 mg/1 Tablet Oral 25 mg/1 Tablet Oral 37.5 mg/1 Tablet Oral 50 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 37.5 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, film coated Oral 75 mg/1 Tablet, film coated, extended release Oral 150 mg/1 Tablet, film coated, extended release Oral 225 mg/1 Tablet, film coated, extended release Oral 37.5 mg/1 Tablet, film coated, extended release Oral 75 mg/1 - Prices
Unit description Cost Unit Venlafaxine HCl 30 225 mg 24 Hour tablet Bottle 276.98USD bottle Effexor XR 30 37.5 mg 24 Hour Capsule Bottle 144.33USD bottle Venlafaxine HCl 30 37.5 mg 24 Hour tablet Bottle 114.46USD bottle Effexor 30 75 mg tablet Bottle 87.83USD bottle Effexor 30 25 mg tablet Bottle 74.82USD bottle Effexor XR 150 mg 24 Hour Capsule 5.87USD capsule Effexor xr 150 mg capsule 5.65USD capsule Effexor XR 75 mg 24 Hour Capsule 5.39USD capsule Effexor xr 75 mg capsule 4.76USD capsule Venlafaxine HCl 150 mg 24 Hour tablet 4.72USD tablet Effexor xr 37.5 mg capsule 4.63USD capsule Venlafaxine HCl 75 mg 24 Hour tablet 4.42USD tablet Effexor 100 mg tablet 2.92USD tablet Effexor 75 mg tablet 2.7USD tablet Effexor 50 mg tablet 2.6USD tablet Effexor 37.5 mg tablet 2.5USD tablet Effexor 25 mg tablet 2.4USD tablet Venlafaxine hcl 100 mg tablet 2.36USD tablet Venlafaxine hcl 75 mg tablet 2.23USD tablet Effexor Xr 150 mg Extended-Release Capsule 2.16USD capsule Venlafaxine hcl 50 mg tablet 2.1USD tablet Effexor Xr 75 mg Extended-Release Capsule 2.05USD capsule Venlafaxine hcl 37.5 mg tablet 2.04USD tablet Venlafaxine hcl 25 mg tablet 1.98USD tablet Apo-Venlafaxine Xr 150 mg Extended-Release Capsule 1.2USD capsule Co Venlafaxine Xr 150 mg Extended-Release Capsule 1.2USD capsule Mylan-Venlafaxine Xr 150 mg Extended-Release Capsule 1.2USD capsule Novo-Venlafaxine Xr 150 mg Extended-Release Capsule 1.2USD capsule Pms-Venlafaxine Xr 150 mg Extended-Release Capsule 1.2USD capsule Ratio-Venlafaxine Xr 150 mg Extended-Release Capsule 1.2USD capsule Sandoz Venlafaxine Xr 150 mg Extended-Release Capsule 1.2USD capsule Apo-Venlafaxine Xr 75 mg Extended-Release Capsule 1.14USD capsule Co Venlafaxine Xr 75 mg Extended-Release Capsule 1.14USD capsule Mylan-Venlafaxine Xr 75 mg Extended-Release Capsule 1.14USD capsule Novo-Venlafaxine Xr 75 mg Extended-Release Capsule 1.14USD capsule Pms-Venlafaxine Xr 75 mg Extended-Release Capsule 1.14USD capsule Ratio-Venlafaxine Xr 75 mg Extended-Release Capsule 1.14USD capsule Sandoz Venlafaxine Xr 75 mg Extended-Release Capsule 1.14USD capsule Effexor Xr 37.5 mg Extended-Release Capsule 1.02USD capsule Apo-Venlafaxine Xr 37.5 mg Extended-Release Capsule 0.57USD capsule Co Venlafaxine Xr 37.5 mg Extended-Release Capsule 0.57USD capsule Mylan-Venlafaxine Xr 37.5 mg Extended-Release Capsule 0.57USD capsule Novo-Venlafaxine Xr 37.5 mg Extended-Release Capsule 0.57USD capsule Pms-Venlafaxine Xr 37.5 mg Extended-Release Capsule 0.57USD capsule Ratio-Venlafaxine Xr 37.5 mg Extended-Release Capsule 0.57USD capsule Sandoz Venlafaxine Xr 37.5 mg Extended-Release Capsule 0.57USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Unlock Additional DataUS5916923 No 1999-06-29 2013-06-28 US CA2126305 No 2006-10-17 2014-06-20 Canada CA2199778 No 2005-12-20 2017-03-12 Canada US6403120 Yes 2002-06-11 2017-09-20 US US6419958 Yes 2002-07-16 2017-09-20 US US6274171 Yes 2001-08-14 2017-09-20 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 215-217 °C (Hydrochloride salt) Not Available water solubility 572 mg/ml (Hydrochloride salt) Not Available - Predicted Properties
Property Value Source Water Solubility 0.23 mg/mL ALOGPS logP 2.69 ALOGPS logP 2.74 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 14.42 ChemAxon pKa (Strongest Basic) 8.91 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 32.7 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 83.02 m3·mol-1 ChemAxon Polarizability 32.33 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9782 Blood Brain Barrier + 0.9382 Caco-2 permeable + 0.852 P-glycoprotein substrate Substrate 0.6534 P-glycoprotein inhibitor I Inhibitor 0.7031 P-glycoprotein inhibitor II Inhibitor 0.8031 Renal organic cation transporter Non-inhibitor 0.5792 CYP450 2C9 substrate Non-substrate 0.7583 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.7664 CYP450 2C9 inhibitor Non-inhibitor 0.6876 CYP450 2D6 inhibitor Inhibitor 0.7287 CYP450 2C19 inhibitor Non-inhibitor 0.7199 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8666 Ames test Non AMES toxic 0.8 Carcinogenicity Non-carcinogens 0.6762 Biodegradation Not ready biodegradable 0.9941 Rat acute toxicity 2.5404 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5486 hERG inhibition (predictor II) Inhibitor 0.6627
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Westenberg HG: Recent advances in understanding and treating social anxiety disorder. CNS Spectr. 2009 Feb;14(2 Suppl 3):24-33. [PubMed:19238127]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- Westenberg HG: Recent advances in understanding and treating social anxiety disorder. CNS Spectr. 2009 Feb;14(2 Suppl 3):24-33. [PubMed:19238127]
- 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]
- 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
- 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]
- Bourin M: [Psychopharmacological profile of venlafaxine]. Encephale. 1999 Jun;25 Spec No 2:21-2; discussion 23-5. [PubMed:10434156]
- 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]
- 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
- SubstrateInhibitor
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- SubstrateInhibitor
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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 June 05, 2020 17:20
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