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Properties

Spectra

Taxonomy

Venlafaxine

Targets (3)Enzymes (5)Transporters (2)Biointeractions (13)

Identification

Name

Venlafaxine

Accession Number

DB00285 (APRD00125)

Type

Small Molecule

Groups

Approved

Description

Venlafaxine (Effexor) is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class first introduced by Wyeth in 1993. It is prescribed for the treatment of clinical depression and anxiety disorders. Due to the pronounced side effects and suspicions that venlafaxine may significantly increase the risk of suicide it is not recommended as a first line treatment of depression. However, it is often effective for depression not responding to SSRIs. Venlafaxine was the sixth most widely-used antidepressant based on the amount of retail prescriptions in the US (17.1 million) in 2006.

Structure

Similar Structures

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
Act Venlafaxine XR	Capsule, extended release	75.0 mg	Oral	Actavis Pharma Company	2008-02-13	Not applicable
Act Venlafaxine XR	Capsule, extended release	37.5 mg	Oral	Actavis Pharma Company	2008-02-13	Not applicable
Act Venlafaxine XR	Capsule, extended release	150.0 mg	Oral	Actavis Pharma Company	2008-02-13	Not applicable
Effexor	Tablet	50 mg/1	Oral	Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.	1993-12-01	2011-05-01
Effexor	Tablet	37.5 mg/1	Oral	Physicians Total Care, Inc.	1993-12-01	2011-05-31
Effexor	Tablet	100 mg/1	Oral	Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.	1993-12-01	2011-05-01
Effexor	Tablet	37.5 mg/1	Oral	Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.	1993-12-01	2011-05-01
Effexor	Tablet	75 mg/1	Oral	Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.	1993-12-01	2011-05-01
Effexor	Tablet	75 mg/1	Oral	Physicians Total Care, Inc.	1993-12-01	2011-05-31
Effexor	Tablet	25 mg/1	Oral	Wyeth Pharmaceuticals Company, a subsidiary of Pfizer Inc.	1993-12-01	2011-05-01

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-venlafaxine XR	Capsule, extended release	37.5 mg	Oral	Apotex Corporation	2013-04-16	Not applicable
Apo-venlafaxine XR	Capsule, extended release	150 mg	Oral	Apotex Corporation	2013-04-16	Not applicable
Apo-venlafaxine XR	Capsule, extended release	75 mg	Oral	Apotex Corporation	2013-04-16	Not applicable
Auro-venlafaxine XR	Capsule, extended release	37.5 mg	Oral	Auro Pharma Inc	2016-03-14	Not applicable
Auro-venlafaxine XR	Capsule, extended release	150 mg	Oral	Auro Pharma Inc	2016-03-14	Not applicable
Auro-venlafaxine XR	Capsule, extended release	75 mg	Oral	Auro Pharma Inc	2016-03-14	Not applicable
Dom-venlafaxine XR	Capsule, extended release	37.5 mg	Oral	Dominion Pharmacal	2013-05-23	Not applicable
Dom-venlafaxine XR	Capsule, extended release	150 mg	Oral	Dominion Pharmacal	2013-05-30	Not applicable
Dom-venlafaxine XR	Capsule, extended release	75 mg	Oral	Dominion Pharmacal	2013-05-23	Not applicable
Effexor	Tablet	50 mg/1	Oral	Directrx	2016-02-02	Not applicable

International/Other Brands

Effexor / 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

For the management of major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder (social phobia), panic disorder with or without agoraphobia, vasomotor symptoms in women with breast cancer and in postmenopausal women, and neuropathic pain.

Associated Conditions

Pharmacodynamics

Venlafaxine potentiates the neurotransmitter activity in the central nervous system. Furthermore, venlafaxine and its metabolite, O-desmethylvenlafaxine (ODV) potently inhibit the reuptake of serotonin and norepinephrine and weakly inhibit dopamine reuptake. Both molecules do not bind to muscarinic, histaminergic, or alpha-1 adrenergic receptors. Pharmacologic activity at these receptors is hypothesized to be associated with the various anticholinergic, sedative, and cardiovascular effects seen with other psychotropic drugs. Both also do not have any monoamine oxidase (MAO) inhibitory activity.

Mechanism of action

The exact mechanism of action of venlafaxine is unknown, but appears to be associated with the its 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. 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	inhibitor	Human
ASodium-dependent noradrenaline transporter	inhibitor	Human
USodium-dependent dopamine transporter	inhibitor	Human

Absorption

Venlafaxine is well absorbed. Food does not effect 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, 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

Most patients overdosing with venlafaxine develop only 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 / 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 CYP2D668A. Found in tandem arrangement with CYP2D64.	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

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	The risk or severity of hemorrhage can be increased when Venlafaxine is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of hemorrhage can be increased when Venlafaxine is combined with (S)-Warfarin.
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 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Venlafaxine.
3,4-Methylenedioxyamphetamine	The risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Venlafaxine.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Venlafaxine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Venlafaxine.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Venlafaxine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Venlafaxine.

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

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]

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)

MSDS

Download (36.5 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Healthy Volunteers	7
1	Completed	Basic Science	Bypass, Gastric / Post-gastrointestinal bypass surgery / Roux-en-Y Gastric Bypass	1
1	Completed	Basic Science	Healthy Volunteers	1
1	Completed	Other	Healthy Volunteers	1
1	Completed	Treatment	Healthy Volunteers	2
1	Not Yet Recruiting	Treatment	Refractory Neuroblastoma / Relapsed Neuroblastoma	1
1	Recruiting	Prevention	Alzheimer's Disease (AD)	1
1, 2	Completed	Treatment	Depression / Major Depressive Disorder (MDD)	2
1, 2	Completed	Treatment	Fibromyalgia	1
2	Active Not Recruiting	Treatment	Major Depressive Disorder (MDD)	1
2	Active Not Recruiting	Treatment	Sickle Cell Disorders	1
2	Completed	Prevention	Cervical Pain	1
2	Completed	Treatment	Bipolar Disorder (BD) / Depressive Disorders	1
2	Completed	Treatment	Cancer, Breast	1
2	Completed	Treatment	Cocaine-Related Disorders	1
2	Completed	Treatment	Depression / Marijuana Abuse	1
2	Completed	Treatment	Depressive Disorders	1
2	Completed	Treatment	Generalized Anxiety Disorder (GAD)	1
2	Completed	Treatment	Major Depressive Disorder (MDD)	3
2	Completed	Treatment	Post-traumatic Neuropathic Pain	1
2	Not Yet Recruiting	Treatment	Acute Lymphoblastic Leukaemias (ALL) / Large B-cell Lymphoma / Refractory CD19+ B-cell Pediatric ALL / Refractory Diffuse Large B Cell Lymphoma / Refractory Large B-cell Lymphoma / Relapsed CD19+ B-cell Pediatric ALL / Relapsed Large B-cell Lymphoma	1
2	Terminated	Treatment	Anxiety Disorders	1
2	Terminated	Treatment	Depression	1
2	Terminated	Treatment	Major Depressive Disorder (MDD)	1
2	Terminated	Treatment	Prostate Cancer	1
2, 3	Completed	Treatment	Alcohol-Related Disorders / Anxiety Disorders	1
2, 3	Completed	Treatment	Depression	1
2, 3	Completed	Treatment	Depression / Suicide, Attempted	1
3	Completed	Prevention	Depression	1
3	Completed	Supportive Care	Bone Mineral Density Quantitative Trait Locus 7	1
3	Completed	Supportive Care	Menopausal Hot Flushes	1
3	Completed	Treatment	Adenocarcinoma, Prostate	1
3	Completed	Treatment	Anxiety Disorders	2
3	Completed	Treatment	Depression	3
3	Completed	Treatment	Depression / Depressive Disorders / Major Depressive Disorder (MDD) / Moods Disorders / Psychiatric Disorder NOS	1
3	Completed	Treatment	Depression / Parkinson's Disease (PD)	1
3	Completed	Treatment	Feeling Anxious	1
3	Completed	Treatment	Healthy Volunteers	1
3	Completed	Treatment	Major Depressive Disorder (MDD)	8
3	Completed	Treatment	Major Depressive Disorder (MDD) / Sleeplessness	1
3	Completed	Treatment	Major Depressive Disorder (MDD) / Treatment Resistant Depression (TRD)	1
3	Completed	Treatment	Panic Disorders	3
3	Completed	Treatment	Social Anxiety Disorder (SAD)	1
3	Recruiting	Treatment	Major Depressive Disorder (MDD)	1
3	Terminated	Supportive Care	Menopausal Hot Flushes / Prostate Cancer	1
3	Terminated	Treatment	Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders	1
4	Active Not Recruiting	Treatment	Obstructive Sleep Apnea (OSA)	1
4	Completed	Not Available	Depression	1
4	Completed	Not Available	Roux En Y Gastric Bypass / Sleeve Gastrectomy	1
4	Completed	Basic Science	Depression	1
4	Completed	Basic Science	Healthy Volunteers	1
4	Completed	Treatment	Anxiety Disorders	1
4	Completed	Treatment	Anxiety Disorders / Depression	1
4	Completed	Treatment	Back Pain / Depression	1
4	Completed	Treatment	Bipolar Disorder (BD)	2
4	Completed	Treatment	Bipolar Disorder (BD) / Depression	1
4	Completed	Treatment	Bipolar Disorder (BD) / Depression / Depressive Disorders	1
4	Completed	Treatment	Bipolar Type II Disorder	1
4	Completed	Treatment	Dementias / Depression	1
4	Completed	Treatment	Depression	6
4	Completed	Treatment	Depression / Depressive Disorders / Major Depressive Disorder (MDD) / Unipolar Depression	1
4	Completed	Treatment	Depression / Mild Cognitive Impairment (MCI)	1
4	Completed	Treatment	Depression / Post Traumatic Stress Disorder (PTSD)	1
4	Completed	Treatment	Dysthymic Disorder / Major Depressive Disorder (MDD) / Spinal Cord Injuries (SCI)	1
4	Completed	Treatment	Major Depressive Disorder (MDD)	8
4	Completed	Treatment	Major Depressive Disorder (MDD) / Recurrences	1
4	Completed	Treatment	Osteoarthritis (OA) / Pain NOS	1
4	Completed	Treatment	Social Phobia	1
4	Completed	Treatment	Traumatic Brain Injury (TBI)	1
4	Completed	Treatment	Vestibular Migraine	1
4	Recruiting	Not Available	Depressive Disorders / Lactation	1
4	Recruiting	Basic Science	Major Depressive Disorder (MDD)	1
4	Recruiting	Diagnostic	Asthma Bronchial / Asthma: [Nos] or [Attack] / Major Depressive Disorder (MDD)	1
4	Recruiting	Diagnostic	Severe Major Depression Disorder	1
4	Recruiting	Health Services Research	Major Depressive Disorder (MDD)	1
4	Recruiting	Treatment	Major Depressive Disorder (MDD) / Major Depressive Episode	1
4	Recruiting	Treatment	Treatment Resistant Major Depressive Disorder / Treatment Resistant Major Depressive Disorder Depression	1
4	Suspended	Treatment	Depression	1
4	Terminated	Treatment	Depression / Relapsing Remitting Multiple Sclerosis (RRMS)	1
4	Terminated	Treatment	Major Depressive Disorder (MDD)	1
4	Unknown Status	Not Available	Major Depressive Disorder (MDD)	1
4	Unknown Status	Treatment	Antidepressive Agents / Fluoxetine / Major Depressive Disorder (MDD) / Pharmacogenetics / Venlafaxine	1
4	Unknown Status	Treatment	Major Depressive Disorder (MDD)	2
4	Withdrawn	Treatment	Major Depressive Disorder (MDD)	1
4	Withdrawn	Treatment	Posttraumatic Stress Disorders	1
Not Available	Active Not Recruiting	Not Available	Anxiety Disorders / Generalized Anxiety Disorder (GAD) / Obsessive Compulsive Disorder (OCD) / Panic Disorders / Post Traumatic Stress Disorder (PTSD) / Social Anxiety Disorder (SAD)	1
Not Available	Active Not Recruiting	Not Available	Cancer, Breast / Depression / Menopausal Hot Flushes / Psychosocial Effects of Cancer and Its Treatment	1
Not Available	Active Not Recruiting	Not Available	Depression/Depressed State	1
Not Available	Active Not Recruiting	Not Available	Major Depressive Disorder (MDD)	1
Not Available	Active Not Recruiting	Treatment	Depression	1
Not Available	Completed	Not Available	Acute Kidney Injury (AKI) / Depression	1
Not Available	Completed	Basic Science	Major Depressive Disorder (MDD)	2
Not Available	Completed	Supportive Care	Cancer, Breast / Menopausal Hot Flushes / Sleep disorders and disturbances	1
Not Available	Completed	Supportive Care	Peripheral Neuropathy	1
Not Available	Completed	Treatment	Alzheimer's Disease (AD) / Depression	1
Not Available	Completed	Treatment	Depression / Depressive Disorders	1
Not Available	Completed	Treatment	Indigestion	1
Not Available	Completed	Treatment	Menopausal Hot Flushes / Menopause / Vasomotor Disturbance	1
Not Available	Completed	Treatment	Pain NOS / Pain, Neuropathic / Spinal Cord Injuries (SCI)	1
Not Available	Completed	Treatment	Spinal Cord Injuries (SCI)	1
Not Available	Enrolling by Invitation	Not Available	Bipolar Disorder (BD)	1
Not Available	Recruiting	Not Available	Obesity, Morbid	1
Not Available	Recruiting	Supportive Care	Stage III Cutaneous Squamous Cell Carcinoma of the Head and Neck AJCC v8 / Stage IV Cutaneous Squamous Cell Carcinoma of the Head and Neck AJCC v8	1
Not Available	Recruiting	Treatment	Alcohol-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 Injuries	1
Not Available	Recruiting	Treatment	Depression / Feeling Anxious / Mild Cognitive Impairment (MCI)	1
Not Available	Recruiting	Treatment	Stroke, Ischemic / Subcortical Aphasia	1
Not Available	Unknown Status	Not Available	Major Depressive Disorder (MDD)	1
Not Available	Unknown Status	Treatment	Major Depressive Disorder (MDD)	2
Not Available	Unknown Status	Treatment	Treatment Resistant Depression (TRD)	1
Not Available	Withdrawn	Supportive Care	Menopausal Hot Flushes	1

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

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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

Form	Route	Strength
Capsule, extended release	Oral	150.0 mg
Capsule, extended release	Oral	75.0 mg
Tablet	Oral	75 mg/1
Tablet	Oral	37.5 mg
Tablet	Oral	50 mg
Tablet	Oral	75 mg
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
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	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)
US5916923	No	1999-06-29	2013-06-28
CA2126305	No	2006-10-17	2014-06-20
CA2199778	No	2005-12-20	2017-03-12
US6403120	Yes	2002-06-11	2017-09-20
US6419958	Yes	2002-07-16	2017-09-20
US6274171	Yes	2001-08-14	2017-09-20

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-0090000000-d413fb5f16658fcc5acb
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-0090000000-182f1032c3f72220679d
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00dj-0910000000-c7a4a25a9bc95faa6db1
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00di-0900000000-7be3d65db3af35be404e
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00di-0900000000-615322444dcf11a7fb8d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0090000000-d212108d9a8267ed7dad
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0090000000-0c4e12d13e69311b26bf
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0bvi-4090000000-8bf2805a95084bfd952a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4i-9520000000-de599153aa118f97ad81
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0ab9-8900000000-6e9f54b654899b486e4d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0ab9-9800000000-d762b2d7edeba1e12b28
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0ab9-9700000000-2b8ebcefcf1274550d32
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-004i-0090000000-c592b4ae2ead9b2bb7ea
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0bvi-4090000000-30b9b5dca017215ebaa4
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0a4i-9620000000-ab905f15470a13b750c5
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0ab9-8900000000-52ec7a86d35dbbd47681
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0ab9-9800000000-7a7cc5b11e1a30499063
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0ab9-9700000000-062f05f9fe2a1540985c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0090000000-8eb971c1dc9a14696c31
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01t9-2090000000-af607e34f7f6700231a4
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9140000000-0b22aeda0f56bf825768
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9300000000-f28ae1a2451e218836c6
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9400000000-c36a2f70d6d9fd69dbfe
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9500000000-43a71bea54c5b09c4c9a
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9400000000-9763935e9812b45adddb
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0bvi-6090000000-fabb5e8a0fd59b8420ca
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-9100000000-b67e5a7dbbd83cf2a7a7
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-9200000000-2300decf19900a1b84e4
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-03di-0090000000-40f0dac6b8ca62d0314f
MS/MS Spectrum - , positive	LC-MS/MS	splash10-01t9-0390000000-7a760936fedd0f48cebf
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9260000000-0b8e3be9620e0271d683
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01t9-2090000000-94fb4781a9910b6b1932
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9140000000-e2c800f5f39f048c545a
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9400000000-e0fa4c4197355be8d0fa
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9500000000-23cbb70f5d3c368966bb
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0a4i-9500000000-998e2271dd7ac0572d54
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not 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 compoundsHydrocarbon derivatives
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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	20	N/A	N/A	21413808 / 23061607
IC 50 (nM)	27	N/A	N/A	20378347
IC 50 (nM)	30	N/A	N/A	21413808
IC 50 (nM)	31	N/A	N/A	18557608
IC 50 (nM)	35	N/A	N/A	20724153
IC 50 (nM)	7	N/A	N/A	21413808
Kd (nM)	8.9	N/A	N/A	9871604
Ki (nM)	102	N/A	N/A	9400006
Ki (nM)	145	N/A	N/A	14744476
Ki (nM)	7.5	N/A	N/A	9400006
Ki (nM)	7.8	N/A	N/A	14744476
Ki (nM)	75.9	N/A	N/A	11454918
Ki (nM)	8.9	N/A	N/A	9537821
Ki (nM)	82	N/A	N/A	11750180 / 14573386

Details1. Sodium-dependent serotonin transporter

Kind: Protein
Organism: Human
Pharmacological action: Yes
Actions: Inhibitor

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]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	149	N/A	N/A	21413808 / 23061607
IC 50 (nM)	535	N/A	N/A	18557608 / 20378347
IC 50 (nM)	581	N/A	N/A	20724153
IC 50 (nM)	61	N/A	N/A	21413808
IC 50 (nM)	754	N/A	N/A	21413808
Kd (nM)	1060	N/A	N/A	9871604
Ki (nM)	1060	N/A	N/A	9537821
Ki (nM)	1420	N/A	N/A	14744476
Ki (nM)	1644	N/A	N/A	9400006
Ki (nM)	1920	N/A	N/A	14744476
Ki (nM)	2269	N/A	N/A	9400006
Ki (nM)	2480	N/A	N/A	11750180
Ki (nM)	2483	N/A	N/A	14573386
Ki (nM)	385	N/A	N/A	18557608
Ki (nM)	6310	N/A	N/A	11454918

Details2. Sodium-dependent noradrenaline transporter

Kind: Protein
Organism: Human
Pharmacological action: Yes
Actions: Inhibitor

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]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	>10000	N/A	N/A	20378347
IC 50 (nM)	19600	N/A	N/A	21413808
IC 50 (nM)	4430	N/A	N/A	21413808 / 23061607
IC 50 (nM)	6670	N/A	N/A	21413808
IC 50 (nM)	7340	N/A	N/A	20724153
Kd (nM)	9300	N/A	N/A	9871604
Ki (nM)	>10000	N/A	N/A	11454918
Ki (nM)	3070	N/A	N/A	14744476
Ki (nM)	6050	N/A	N/A	14744476
Ki (nM)	7647	N/A	N/A	11750180 / 14573386
Ki (nM)	9300	N/A	N/A	9537821

Details3. Sodium-dependent dopamine transporter

Kind: Protein
Organism: Human
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

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Human
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

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]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
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]
Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

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]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
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]

Details3. Cytochrome P450 2C9

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid 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 oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 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]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]

Details4. Cytochrome P450 2C19

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 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]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Details5. Cytochrome P450 2B6

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid 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 oxidizes a variety of structurally un...
Gene Name: CYP2B6
Uniprot ID: P20813
Uniprot Name: Cytochrome P450 2B6
Molecular Weight: 56277.81 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]

Transporters

Details1. Multidrug resistance protein 1

Kind: Protein
Organism: Human
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

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]

Details2. ATP-binding cassette sub-family G member 2

Kind: Protein
Organism: Human
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 December 16, 2018 06:37

Venlafaxine

Identification

Structure for Venlafaxine (DB00285)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Enzymes

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Transporters

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