VENLAFAXINE BESYLATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H27NO2.C6H6O3S
Molecular Weight	435.577
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC=CC=C1.COC2=CC=C(C=C2)C(CN(C)C)C3(O)CCCCC3

InChI

InChIKey=PTEFWGKCGCNHDM-UHFFFAOYSA-N

InChI=1S/C17H27NO2.C6H6O3S/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14;7-10(8,9)6-4-2-1-3-5-6/h7-10,16,19H,4-6,11-13H2,1-3H3;1-5H,(H,7,8,9)

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/16140280

Venlafaxine is an arylalkanolamine serotonin-norepinephrine reuptake inhibitor, which is sold under several brand names; one of them is venlafaxine hydrochloride. Venlafaxine hydrochloride is a venlafaxine extended release tablets, which are indicated for the treatment of major depressive disorder (MDD). Efficacy of venlafaxine in MDD was shown in both short-term trials and a longer-term trial in MDD. A major depressive episode (DSM-IV) implies a prominent and relatively persistent depressed mood or the loss of interest or pleasure in nearly all activities, representing a change from previous functioning, and includes the presence of at least five of the following nine symptoms during the same two-week period. In addition, venlafaxine hydrochloride is indicated for the treatment of social anxiety (SAD), also known as social phobia. Social Anxiety Disorder (DSM-IV) is characterized by a marked and persistent fear of 1 or more social or performance situations in which others expose to unfamiliar people or to possible scrutiny the person. Exposure to the feared situation almost invariably provokes anxiety, which may approach the intensity of a panic attack. The feared situations are avoided or endured with intense anxiety or distress. The mechanism of the antidepressant action of venlafaxine in humans is believed to be associated with its potentiation of neurotransmitter activity in the CNS. Preclinical studies have shown that venlafaxine and its active metabolite, O-desmethylvenlafaxine (ODV), are potent inhibitors of neuronal serotonin and norepinephrine reuptake and weak inhibitors of dopamine reuptake.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16140280	Inhibitor 8297		1.26 µM [Ki]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16140280	Inhibitor 8297		74.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf	Primary		Approved 8429	VENLAFAXINE HYDROCHLORIDE Approved Use Major Depressive Disorder Venlafaxine Extended Release Tablets (venlafaxine hydrochloride) are indicated for the treatment of major depressive disorder (MDD). Efficacy of venlafaxine in MDD was shown in both short-term trials and a longer-term trial in MDD. A major depressive episode (DSM-IV) implies a prominent and relatively persistent (nearly every day for at least 2 weeks) depressed mood or the loss of interest or pleasure in nearly all activities, representing a change from previous functioning, and includes the presence of at least five of the following nine symptoms during the same two-week period: depressed mood, markedly diminished interest or pleasure in usual activities, significant change in weight and/or appetite, insomnia or hypersomnia, psychomotor agitation or retardation, increased fatigue, feelings of guilt or worthlessness, slowed thinking or impaired concentration, a suicide attempt or suicidal ideation. Social Anxiety Disorder Venlafaxine Extended Release Tablets are indicated for the treatment of Social Anxiety Disorder (SAD), also known as Social Phobia, as defined in DSM-IV. Social Anxiety Disorder (DSM-IV) is characterized by a marked and persistent fear of 1 or more social or performance situations in which the person is exposed to unfamiliar people or to possible scrutiny by others. Exposure to the feared situation almost invariably provokes anxiety, which may approach the intensity of a panic attack. The feared situations are avoided or endured with intense anxiety or distress. The avoidance, anxious anticipation, or distress in the feared situation(s) interferes significantly with the person's normal routine, occupational or academic functioning, or social activities or relationships, or there is a marked distress about having the phobias. Lesser degrees of performance anxiety or shyness generally do not require psychopharmacological treatment. Launch Date 2008
Social anxiety disorder 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf	Primary		Approved 8429	VENLAFAXINE HYDROCHLORIDE Approved Use Major Depressive Disorder Venlafaxine Extended Release Tablets (venlafaxine hydrochloride) are indicated for the treatment of major depressive disorder (MDD). Efficacy of venlafaxine in MDD was shown in both short-term trials and a longer-term trial in MDD. A major depressive episode (DSM-IV) implies a prominent and relatively persistent (nearly every day for at least 2 weeks) depressed mood or the loss of interest or pleasure in nearly all activities, representing a change from previous functioning, and includes the presence of at least five of the following nine symptoms during the same two-week period: depressed mood, markedly diminished interest or pleasure in usual activities, significant change in weight and/or appetite, insomnia or hypersomnia, psychomotor agitation or retardation, increased fatigue, feelings of guilt or worthlessness, slowed thinking or impaired concentration, a suicide attempt or suicidal ideation. Social Anxiety Disorder Venlafaxine Extended Release Tablets are indicated for the treatment of Social Anxiety Disorder (SAD), also known as Social Phobia, as defined in DSM-IV. Social Anxiety Disorder (DSM-IV) is characterized by a marked and persistent fear of 1 or more social or performance situations in which the person is exposed to unfamiliar people or to possible scrutiny by others. Exposure to the feared situation almost invariably provokes anxiety, which may approach the intensity of a panic attack. The feared situations are avoided or endured with intense anxiety or distress. The avoidance, anxious anticipation, or distress in the feared situation(s) interferes significantly with the person's normal routine, occupational or academic functioning, or social activities or relationships, or there is a marked distress about having the phobias. Lesser degrees of performance anxiety or shyness generally do not require psychopharmacological treatment. Launch Date 2008

C_max

Value	Dose	Analyte	Population
260 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DESVENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
97.9 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DESVENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
26.9 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
150 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
2926 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DESVENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
1536.3 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Analyte	Population
12.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DESVENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
12.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DESVENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
7.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
10.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

F_unbound

Value	Dose	Analyte	Population
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DESVENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DESVENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
73% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	75 mg 1 times / day steady-state, oral dose: 75 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
73% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s016lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VENLAFAXINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

Doses

Dose	Population	Adverse events
225 mg 1 times / day multiple, oral Recommended Dose: 225 mg, 1 times / day Route: oral Route: multiple Dose: 225 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf	unhealthy, adult n = 277 Health Status: unhealthy Condition: Social Anxiety Disorder Age Group: adult Population Size: 277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf	Other AEs: Headache, Asthenia... Other AEs: Headache (34%) Asthenia (17%) Flu syndrome (6%) Accidental injury (5%) Abdominal pain (4%) Hypertension (5%) Vasodilatation (3%) Palpitation (3%) Nausea (29%) Anorexia (20%) Constipation (8%) Diarrhea (6%) Vomiting (3%) Eructation (2%) Weight loss (4%) Insomnia (23%) Dry mouth (17%) Dizziness (16%) Somnolence (16%) Nervousness (11%) Libido decreased (9%) Anxiety (5%) Agitation (4%) Tremor (4%) Abnormal dreams (4%) Paresthesia (3%) Twitching (2%) Yawn (5%) Sinusitis (2%) Sweating (13%) Abnormal vision (6%) Abnormal ejaculation (16%) Impotence (10%) Orgasmic disorders and disturbances (8%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf
225 mg 1 times / day multiple, oral Recommended Dose: 225 mg, 1 times / day Route: oral Route: multiple Dose: 225 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf	unhealthy, adult n = 357 Health Status: unhealthy Condition: Major Depressive Disorder Age Group: adult Population Size: 357 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf	Other AEs: Asthenia, Vasodilatation... Other AEs: Asthenia (8%) Vasodilatation (4%) Hypertension (4%) Nausea (31%) Constipation (8%) Anorexia (8%) Vomiting (4%) Flatulence (4%) Weight loss (3%) Dizziness (20%) Somnolence (17%) Insomnia (17%) Dry mouth (12%) Nervousness (10%) Abnormal dreams (7%) Tremor (5%) Depression (3%) Paresthesia (3%) Libido decreased (3%) Agitation (3%) Pharyngitis (7%) Yawn (3%) Sweating (14%) Abnormal vision (4%) Abnormal ejaculation (16%) Impotence (4%) Inhibited female orgasm (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	substrate 1037	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 97 P-gp 1461 CYP1A2 1524 CYP2C 19	CYP2C19 991 P-gp 1537	P-gp 257 BCRP 75 OCT1 35 MRP2 111 OATP1B1 26 CYP1A2 701

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1520-6394(1998)7:1+%3C24::AID-DA7%3E3.0.CO;2-F	minimal or no
CYP2C 34	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1520-6394(1998)7:1+%3C24::AID-DA7%3E3.0.CO;2-F	minimal or no
CYP3A4 1925	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1520-6394(1998)7:1+%3C24::AID-DA7%3E3.0.CO;2-F	minimal or no
P-gp 1650	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3268186/	no [IC50 >100 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1520-6394(1998)7:1+%3C24::AID-DA7%3E3.0.CO;2-F	weak	yes (co-administration study) Comment: info taken from abstract; Coadministration with risperidone increased AUC of risperidone by 32%. See https://pubmed.ncbi.nlm.nih.gov/24964257/ Sources: https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1520-6394(1998)7:1+%3C24::AID-DA7%3E3.0.CO;2-F
BCRP 773	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/23897419/	yes
CYP1A2 1692	inducer 1573 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2014.955831	yes
MRP2 475	inducer 1573 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2014.955831	yes
OATP1B1 803	inducer 1573 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2014.955831	yes
OCT1 543	inducer 1573 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2014.955831	yes
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/23897419/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020699ap_effexor_clinphrmr_admindoc_.pdf#page=7 Page: 7.0	inconclusive	yes (co-administration study) Comment: Coadministration with ketoconazole (CYP3A4 inhibitor) increased AUC by 70%. See https://pubmed.ncbi.nlm.nih.gov/24964257/ Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020699ap_effexor_clinphrmr_admindoc_.pdf#page=7 Page: 7.0
P-gp 1537	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3268186/	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10192828/	yes	weak (co-administration study) Comment: Coadministration with voriconazole (CYP2C9 inhibitor) increased AUC by 31%. See https://pubmed.ncbi.nlm.nih.gov/24964257/ Sources: https://pubmed.ncbi.nlm.nih.gov/10192828/
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10192828/	yes	weak (co-administration study) Comment: Coadministration with voriconazole (CYP2C9 inhibitor) increased AUC by 31%. See https://pubmed.ncbi.nlm.nih.gov/24964257/ Sources: https://pubmed.ncbi.nlm.nih.gov/10192828/
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020699s110s111lbl.pdf#page=27 Page: 27.0	yes	yes (co-administration study) Comment: Coadministration with diphenhydramine increased AUC 2-fold; Coadministration with ketoconazole increased AUc by 70%. See https://pubmed.ncbi.nlm.nih.gov/24964257/ Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020699s110s111lbl.pdf#page=27 Page: 27.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 100	inhibitor 1626 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0014299916302874?via%3Dihub
hERG 1647	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3002179/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9943	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9943
ChemicalBook	CB42567671	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB42567671
ChemicalBook	CB7136180	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7136180
MolPort	MolPort-003-666-534	https://www.molport.com/shop/molecule-link/MolPort-003-666-534
eMolecules	902654	https://www.emolecules.com/cgi-bin/more?vid=902654

PubMed

Title	Date	PubMed
Hot flashes: aetiology and management.	2001	11587246
Attaining remission in generalized anxiety disorder: venlafaxine extended release comparative data.	2001	11577788
Overview of different pharmacotherapies for attaining remission in generalized anxiety disorder.	2001	11577786
Venlafaxine extended-release: a review of its use in the management of major depression.	2001	11524036
Do some antidepressants work faster than others?	2001	11444763
Evidence of early onset of antidepressant effect in randomized controlled trials.	2001	11229783
Incidence of sexual dysfunction associated with antidepressant agents: a prospective multicenter study of 1022 outpatients. Spanish Working Group for the Study of Psychotropic-Related Sexual Dysfunction.	2001	11229449
Asymptomatic QTc prolongation associated with quetiapine fumarate overdose in a patient being treated with risperidone.	2001 Apr	11393275
Sustained administration of the antidepressant venlafaxine in rats: pharmacokinetic and pharmacodynamic findings.	2001 Apr	11330339
Specific effect of venlafaxine on single and repetitive experimental painful stimuli in humans.	2001 Apr	11309553
Effect of venlafaxine versus fluoxetine on metabolism of dextromethorphan, a CYP2D6 probe.	2001 Apr	11304901
Prefrontal changes and treatment response prediction in depression.	2001 Apr	11296311
[Current drug treatment. Effects of antidepressive agents in nervous and stress-related disorders].	2001 Apr 2	11307357
[Pharmacotherapy for neuropathic pain caused by injury to the afferent nerve fibers].	2001 Apr 28	11370425
Venlafaxine in the treatment of postpartum depression.	2001 Aug	11561929
Flushing in a menopausal woman taking venlafaxine.	2001 Aug	11481177
Topiramate in venlafaxine-induced visual hallucinations in an obese patient with a posterior cerebral artery infarction.	2001 Aug	11476137
Successful use of cardiac allograft from serotonin antagonist intoxication.	2001 Aug 15	11502988
Microdialysis in freely moving mice: determination of acetylcholine, serotonin and noradrenaline release in galanin transgenic mice.	2001 Aug 15	11489302
A review of the pharmacological and clinical profile of mirtazapine.	2001 Fall	11607047
Comparison of antidepressant activity in 4- and 40-week-old male mice in the forced swimming test: involvement of 5-HT1A and 5-HT1B receptors in old mice.	2001 Feb	11243491
Screening for detection of new antidepressants, neuroleptics, hypnotics, and their metabolites in urine by GC-MS developed using rat liver microsomes.	2001 Feb	11206046
Antidepressants as analgesics: a review of randomized controlled trials.	2001 Jan	11212591
Fluoxetine (Sarafem) for premenstrual dysphoric disorder.	2001 Jan 22	11177220
Sertraline, paroxetine, and venlafaxine in refugee posttraumatic stress disorder with depression symptoms.	2001 Jul	11534876
In vitro effects of St. John's wort extract and hyperforin on 5 HT uptake and efflux in human blood platelets.	2001 Jul	11518065
Neuroimaging profiles and the differential therapies of depression.	2001 Jul	11448371
Brain blood flow changes in depressed patients treated with interpersonal psychotherapy or venlafaxine hydrochloride: preliminary findings.	2001 Jul	11448369
Venlafaxine extended release (ER) in the treatment of generalised anxiety disorder: twenty-four-week placebo-controlled dose-ranging study.	2001 Jul	11435263
Even low-dose treatment of venlafaxine may provoke recurrence of hypertension in an Asian patient?	2001 Jul-Aug	11569474
The Stanley Foundation Bipolar Network. I. Rationale and methods.	2001 Jun	11450179
Antidepressant discontinuation (withdrawal) symptoms presenting as 'stroke'.	2001 Jun	11448088
Substitution of an SSRI with bupropion sustained release following SSRI-induced sexual dysfunction.	2001 Mar	11305705
Pharmacologic treatment of generalized anxiety disorder.	2001 Mar	11225503
Simultaneous screen for microsomal stability and metabolite profile by direct injection turbulent-laminar flow LC-LC and automated tandem mass spectrometry.	2001 May 1	11354502
Addition of olanzapine for treatment-resistant depression.	2001 Oct	11579017
Pregnancy outcome following gestational exposure to venlafaxine: a multicenter prospective controlled study.	2001 Oct	11579012
Practitioner versus medication-expert opinion on psychiatric pharmacotherapy of mentally retarded patients with mental disorders.	2001 Oct 1	11596698
Once-daily venlafaxine extended release (XR) vs. fluoxetine for the treatment of depression.	2001 Sep	11592259
On-line capillary electrophoresis-electrospray mass spectrometry for the stereoselective analysis of drugs and metabolites.	2001 Sep	11589295
Antidepressants in social anxiety disorder.	2001 Sep	11588653
The pharmacoeconomics of venlafaxine in depression.	2001 Sep	11570029
The clinical, psychosocial, and pharmacoeconomic ramifications of remission.	2001 Sep	11570028
Effects of chronic tramadol on pre- and post-synaptic measures of monoamine function.	2001 Sep	11565620
Postmortem tissue concentrations of venlafaxine.	2001 Sep 15	11516890
High-performance liquid chromatographic method to screen and quantitate seven selective serotonin reuptake inhibitors in human serum.	2001 Sep 25	11587344
[Changes in antidepressants consumption in the health area of Zamora from 1996 to 1999].	2001 Sep 30	11602104

Patents

Sample Use Guides

In Vivo Use Guide

Major Depressive Disorder: for most patients, the recommended starting dose for Venlafaxine Extended Release Tablets is 75 mg/day, administered in a single dose. In the clinical trials establishing the efficacy of venlafaxine hydrochloride extended-release capsules in moderately depressed outpatients, the initial dose of venlafaxine was 75 mg/day. For some patients, it may be desirable to start at 37.5 mg/day for 4 to 7 days, to allow new patients to adjust to the medication before increasing to 75 mg/day. While the relationship between dose and antidepressant response for venlafaxine hydrochloride extended-release capsules has not been adequately explored, patients not responding to the initial 75 mg/day dose may benefit from dose increases to a maximum of approximately 225 mg/day. Dose increases should be in increments of up to 75 mg/day, as needed, and should be made at intervals of not less than 4 days, since steady state plasma levels of venlafaxine and its major metabolites are achieved in most patients by day 4. In the clinical trials establishing efficacy, upward titration was permitted at intervals of 2 weeks or more; the average doses were about 140 to 180 mg/day. It should be noted that, while the maximum recommended dose for moderately depressed outpatients is also 225 mg/day for venlafaxine hydrochloride immediate-release tablets, more severely depressed inpatients in one study of the development program for that product responded to a mean dose of 350 mg/day (range of 150 to 375 mg/day). Whether or not higher doses of Venlafaxine Extended Release Tablets are needed for more severely depressed patients is unknown; however, the experience with venlafaxine hydrochloride extended-release capsule doses higher than 225 mg/day is very limited. Social Anxiety Disorder (Social Phobia): the recommended dose is 75 mg/day, administered in a single dose. There was no evidence that higher doses confer any additional benefit.

Route of Administration: Oral

In Vitro Use Guide

In vitro radioligand binding studies were carried out in rat brain membranes to assess the affinity of various reuptake inhibitors for the serotonin (5-hydroxytryptamine, 5-HT) and the norepinephrine transporters using the selective ligands [3H]cyanoimipramine and [3H]nisoxetine, respectively. Venlafaxine, a dual 5-HT and norepinephrine reuptake inhibitor, displayed only a moderate affinity for the 5-HT transporter (Ki = 74 nM) and a very low affinity for the norepinephrine transporter (Ki = 1.26 microM). The relatively low affinities of venlafaxine contrast with its potent in vivo 5-HT and norepinephrine reuptake blocking properties. These results raise the possibility that the in vivo effects on the 5-HT and norepinephrine reuptake observed with venlafaxine may not be mediated solely by its binding to the [3H]cyanoimipramine and [3H]nisoxetine binding sites.

Name

Type

Language

VENLAFAXINE BESYLATE

Common Name

English

CYCLOHEXANOL, 1-(2-(DIMETHYLAMINO)-1-(4-METHOXYPHENYL)ETHYL)-, BENZENESULFONATE (SALT)

Systematic Name

English

VENLAFAXINE BESYLATE ANHYDROUS

Common Name

English

CYCLOHEXANOL, 1-(2-(DIMETHYLAMINO)-1-(4-METHOXYPHENYL)ETHYL)-, BENZENESULFONATE (1:1)

Systematic Name

English

Code System Code Type Description

RXCUI

2607741

Created by admin on Sat Dec 16 14:04:48 GMT 2023 , Edited by admin on Sat Dec 16 14:04:48 GMT 2023

PRIMARY

PUBCHEM

10173527

Created by admin on Sat Dec 16 14:04:48 GMT 2023 , Edited by admin on Sat Dec 16 14:04:48 GMT 2023

PRIMARY

FDA UNII

1R8EN4W1EG

Created by admin on Sat Dec 16 14:04:48 GMT 2023 , Edited by admin on Sat Dec 16 14:04:48 GMT 2023

PRIMARY

CAS

609345-58-6

Created by admin on Sat Dec 16 14:04:48 GMT 2023 , Edited by admin on Sat Dec 16 14:04:48 GMT 2023

PRIMARY

ACTIVE MOIETY


					GRZ5RCB1QG

VENLAFAXINE

SUBSTANCE RECORD


					1R8EN4W1EG

VENLAFAXINE BESYLATE

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/16140280

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022104s015lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/16140280

C_max

T_1/2

F_unbound

Drug as perpetrator