U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H27NO2.C6H6O3S
Molecular Weight 435.5788
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VENLAFAXINE BESYLATE

SMILES

CN(C)CC(c1ccc(cc1)OC)C2(CCCCC2)O.c1ccc(cc1)S(=O)(=O)O

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

Molecular Formula C17H27NO2
Molecular Weight 277.4024
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C6H6O3S
Molecular Weight 158.1764
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: Known to be CNS penetrant in rat. Human data not available.

Originator

Curator's Comment:: Venlafaxine was first synthesized in the early 1980s by researchers at Wyeth Pharmaceuticals-- recognized venlafaxine’s promise as an important antidepressant and pressed forward with its development. Wyeth launched venlafaxine for the treatment of depression in the United States in early 1994 under the trade name Effexor. # Wyeth scientists: John Yardley, Morris Husbands, and Eric Muth

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.26 µM [Ki]
74.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.21124159E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
260 ng/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2926 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.5 h
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
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
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
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%
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%
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%
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

Doses

DosePopulationAdverse 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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
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:
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
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:
AEs

AEs

AESignificanceDosePopulation
Impotence 10%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Nervousness 11%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Sweating 13%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Abnormal ejaculation 16%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Dizziness 16%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Somnolence 16%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Asthenia 17%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Dry mouth 17%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Eructation 2%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Sinusitis 2%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Twitching 2%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Anorexia 20%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Insomnia 23%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Nausea 29%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Palpitation 3%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Paresthesia 3%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Vasodilatation 3%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Vomiting 3%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Headache 34%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Abdominal pain 4%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Abnormal dreams 4%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Agitation 4%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Tremor 4%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Weight loss 4%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Accidental injury 5%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Anxiety 5%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Hypertension 5%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Yawn 5%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Abnormal vision 6%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Diarrhea 6%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Flu syndrome 6%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Constipation 8%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Orgasmic disorders and disturbances 8%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Libido decreased 9%
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:
unhealthy, adult
n = 277
Health Status: unhealthy
Condition: Social Anxiety Disorder
Age Group: adult
Population Size: 277
Sources:
Nervousness 10%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Dry mouth 12%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Sweating 14%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Abnormal ejaculation 16%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Insomnia 17%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Somnolence 17%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Dizziness 20%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Agitation 3%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Depression 3%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Inhibited female orgasm 3%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Libido decreased 3%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Paresthesia 3%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Weight loss 3%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Yawn 3%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Nausea 31%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Abnormal vision 4%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Flatulence 4%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Hypertension 4%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Impotence 4%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Vasodilatation 4%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Vomiting 4%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Tremor 5%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Abnormal dreams 7%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Pharyngitis 7%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Anorexia 8%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Asthenia 8%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
Constipation 8%
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:
unhealthy, adult
n = 357
Health Status: unhealthy
Condition: Major Depressive Disorder
Age Group: adult
Population Size: 357
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
minimal or no
minimal or no
minimal or no
no [IC50 >100 uM]
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/
yes
yes
yes
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
yes (co-administration study)
Comment: Coadministration with ketoconazole (CYP3A4 inhibitor) increased AUC by 70%. See https://pubmed.ncbi.nlm.nih.gov/24964257/
Page: 7.0
no
yes
weak (co-administration study)
Comment: Coadministration with voriconazole (CYP2C9 inhibitor) increased AUC by 31%. See https://pubmed.ncbi.nlm.nih.gov/24964257/
yes
weak (co-administration study)
Comment: Coadministration with voriconazole (CYP2C9 inhibitor) increased AUC by 31%. See https://pubmed.ncbi.nlm.nih.gov/24964257/
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/
Page: 27.0
Tox targets
PubMed

PubMed

TitleDatePubMed
Hot flashes: aetiology and management.
2001
Hormone replacement in women with a history of breast cancer.
2001
Venlafaxine extended-release: a review of its use in the management of major depression.
2001
Serotonergic and noradrenergic reuptake inhibitors: prediction of clinical effects from in vitro potencies.
2001
Pharmacotherapy of generalized anxiety disorder.
2001
Antidepressant discontinuation syndromes.
2001
Specific effect of venlafaxine on single and repetitive experimental painful stimuli in humans.
2001 Apr
Effect of venlafaxine versus fluoxetine on metabolism of dextromethorphan, a CYP2D6 probe.
2001 Apr
Sustained response to open-label venlafaxine in drug-resistant major depression.
2001 Apr
Venlafaxine in the treatment of postpartum depression.
2001 Aug
[Serotonin-noradrenaline reuptake inhibitors(SNRIs)].
2001 Aug
[14C]Serotonin uptake and [O-methyl-11C]venlafaxine kinetics in porcine brain.
2001 Aug
Flushing in a menopausal woman taking venlafaxine.
2001 Aug
Topiramate in venlafaxine-induced visual hallucinations in an obese patient with a posterior cerebral artery infarction.
2001 Aug
Mirtazapine versus venlafaxine in hospitalized severely depressed patients with melancholic features.
2001 Aug
S33005, a novel ligand at both serotonin and norepinephrine transporters: II. Behavioral profile in comparison with venlafaxine, reboxetine, citalopram, and clomipramine.
2001 Aug
Successful use of cardiac allograft from serotonin antagonist intoxication.
2001 Aug 15
Microdialysis in freely moving mice: determination of acetylcholine, serotonin and noradrenaline release in galanin transgenic mice.
2001 Aug 15
A review of the pharmacological and clinical profile of mirtazapine.
2001 Fall
Nonaqueous capillary electrophoresis-mass spectrometry for separation of venlafaxine and its phase I metabolites.
2001 Feb
Reboxetine plus citalopram for refractory depression not responding to venlafaxine: possible mechanisms.
2001 Feb
In vitro effects of St. John's wort extract and hyperforin on 5 HT uptake and efflux in human blood platelets.
2001 Jul
Efficacy of venlafaxine extended release in patients with major depressive disorder and comorbid generalized anxiety disorder.
2001 Jul
[Depressive disorders and antidepressive therapy. A comparison of neurology practice and psychiatric clinic].
2001 Jul
Neuroimaging profiles and the differential therapies of depression.
2001 Jul
Functional brain circuits in major depression and remission.
2001 Jul
Even low-dose treatment of venlafaxine may provoke recurrence of hypertension in an Asian patient?
2001 Jul-Aug
Symptom reduction and suicide risk in patients treated with placebo in antidepressant clinical trials: a replication analysis of the Food and Drug Administration Database.
2001 Jun
The health economic impact of antidepressant usage from a payer's perspective: a multinational study.
2001 Jun
The Stanley Foundation Bipolar Network. I. Rationale and methods.
2001 Jun
Antidepressant discontinuation (withdrawal) symptoms presenting as 'stroke'.
2001 Jun
Short-term administration of fluoxetine and venlafaxine decreases corticosteroid receptor mRNA expression in the rat hippocampus.
2001 Jun 29
Use of antidepressants in treatment of comorbid diabetes mellitus and depression as well as in diabetic neuropathy.
2001 Mar
Venlafaxine withdrawal syndrome not prevented by maprotiline, but resolved by sertraline.
2001 Mar
Breast cancer and hot flashes. Options for relief.
2001 Mar
Treatment of neuropathic pain with venlafaxine.
2001 May
Recurrent depression with vagus nerve stimulation.
2001 May
Addition of olanzapine for treatment-resistant depression.
2001 Oct
Pregnancy outcome following gestational exposure to venlafaxine: a multicenter prospective controlled study.
2001 Oct
Practitioner versus medication-expert opinion on psychiatric pharmacotherapy of mentally retarded patients with mental disorders.
2001 Oct 1
Once-daily venlafaxine extended release (XR) vs. fluoxetine for the treatment of depression.
2001 Sep
On-line capillary electrophoresis-electrospray mass spectrometry for the stereoselective analysis of drugs and metabolites.
2001 Sep
Antidepressants in social anxiety disorder.
2001 Sep
Effects of chronic tramadol on pre- and post-synaptic measures of monoamine function.
2001 Sep
The combined use of bupropion, lithium, and venlafaxine during ECT: a case of prolonged seizure activity.
2001 Sep
Long-term outcome after ECT for catatonic depression.
2001 Sep
Postmortem tissue concentrations of venlafaxine.
2001 Sep 15
High-performance liquid chromatographic method to screen and quantitate seven selective serotonin reuptake inhibitors in human serum.
2001 Sep 25
[Changes in antidepressants consumption in the health area of Zamora from 1996 to 1999].
2001 Sep 30
Rapid high-performance liquid chromatographic measurement of venlafaxine and O-desmethylvenlafaxine in human plasma. Application to management of acute intoxications.
2001 Sep 5
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:29:53 UTC 2021
Edited
by admin
on Sat Jun 26 05:29:53 UTC 2021
Record UNII
1R8EN4W1EG
Record Status Validated (UNII)
Record Version
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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
PUBCHEM
10173527
Created by admin on Sat Jun 26 05:29:53 UTC 2021 , Edited by admin on Sat Jun 26 05:29:53 UTC 2021
PRIMARY
FDA UNII
1R8EN4W1EG
Created by admin on Sat Jun 26 05:29:53 UTC 2021 , Edited by admin on Sat Jun 26 05:29:53 UTC 2021
PRIMARY
CAS
609345-58-6
Created by admin on Sat Jun 26 05:29:53 UTC 2021 , Edited by admin on Sat Jun 26 05:29:53 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY