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Details

Stereochemistry RACEMIC
Molecular Formula C16H25NO2.C7H6O2
Molecular Weight 385.4965
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESVENLAFAXINE BENZOATE

SMILES

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

InChI

InChIKey=DGJCDBBBNQGOIR-UHFFFAOYSA-N
InChI=1S/C16H25NO2.C7H6O2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16;8-7(9)6-4-2-1-3-5-6/h6-9,15,18-19H,3-5,10-12H2,1-2H3;1-5H,(H,8,9)

HIDE SMILES / InChI

Molecular Formula C7H6O2
Molecular Weight 122.1213
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H25NO2
Molecular Weight 263.3752
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16675639 | http://adisinsight.springer.com/drugs/800000550

Desvenlafaxine is a dual serotonin and norepinephrine reuptake inhibitor in vitro and in vivo that demonstrates good brain-to-plasma ratios. Desvenlafaxine has demonstrated antidepressant effects in preclinical studies. Pfizer is developing an oral, extended-release formulation of desvenlafaxine for the treatment of major depressive disorder. Desvenlafaxine has been registered and is available on the market for the treatment of major depressive disorder in adults.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PRISTIQ

Approved Use

PRISTIQ (DESVENLAFAXINE SUCCINATE), a selective serotonin and norepinephrine reuptake inhibitor, is indicated for the treatment of major depressive disorder.

Launch Date

1.40849277E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
39.6 ng/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESVENLAFAXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
591 ng × h/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESVENLAFAXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.9 h
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESVENLAFAXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESVENLAFAXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
750 mg single, oral
MTD
healthy, 23.95
n = 11
Other AEs: Vomiting...
900 mg single, oral
Highest studied dose
healthy, 27.5 ± 9.0
n = 6
DLT: Vomiting...
Other AEs: Nausea...
600 mg 1 times / day multiple, oral
Highest studied dose
healthy, 32.9 ± 4.7
n = 9
DLT: Orthostatic hypotension...
3500 mg single, oral
Overdose
Dose: 3500 mg
Route: oral
Route: single
Dose: 3500 mg
Sources: Page: p.6
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: F
Population Size: 1
Sources: Page: p.6
Disc. AE: Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Serotonin syndrome
Sources: Page: p.6
450 mg 1 times / day multiple, oral
MTD
healthy, 34.9 ± 7.4
n = 9
Other AEs: Nausea...
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Disc. AE: Suicidal ideation, Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Serotonin syndrome
Neuroleptic malignant syndrome
Blood pressure increased
Bleeding
Glaucoma
Mania
Hypomania
Cardiovascular disease, unspecified
Unspecified cerebrovascular disease
Elevated cholesterol
Elevated triglycerides
Seizure
Hyponatremia
Sources: Page: p.1
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Other AEs: Lightheadedness, Sickness/nausea...
Other AEs:
Lightheadedness (below serious, 11 patient)
Sickness/nausea (below serious, 11 patient)
Drowsiness (below serious, 7 patients)
Insomnia (below serious, 5 patients)
Decreased appetite (below serious, 6 patients)
Indigestion (below serious, 4 patients)
Soft stools (below serious, 5 patients)
Dry mouth (below serious, 3 patients)
Sources:
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Other AEs: Sleep decreased, Daytime sleepiness...
Other AEs:
Sleep decreased (below serious, 10 patients)
Daytime sleepiness (below serious, 9 patients)
Headache (below serious, 9 patients)
Nausea (below serious, 9 patients)
Dry mouth (below serious, 7 patients)
Agitation (below serious, 5 patients)
Dizziness (below serious, 5 patients)
Sweating (below serious, 5 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Vomiting 27%
750 mg single, oral
MTD
healthy, 23.95
n = 11
Vomiting 67%
DLT
900 mg single, oral
Highest studied dose
healthy, 27.5 ± 9.0
n = 6
Nausea severe, 33%
900 mg single, oral
Highest studied dose
healthy, 27.5 ± 9.0
n = 6
Orthostatic hypotension 67%
DLT
600 mg 1 times / day multiple, oral
Highest studied dose
healthy, 32.9 ± 4.7
n = 9
Serotonin syndrome Disc. AE
3500 mg single, oral
Overdose
Dose: 3500 mg
Route: oral
Route: single
Dose: 3500 mg
Sources: Page: p.6
healthy, 33
n = 1
Health Status: healthy
Age Group: 33
Sex: F
Population Size: 1
Sources: Page: p.6
Nausea 67%
450 mg 1 times / day multiple, oral
MTD
healthy, 34.9 ± 7.4
n = 9
Bleeding Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Blood pressure increased Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Cardiovascular disease, unspecified Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Elevated cholesterol Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Elevated triglycerides Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Glaucoma Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Hypomania Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Hyponatremia Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Mania Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Neuroleptic malignant syndrome Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Seizure Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Serotonin syndrome Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Suicidal ideation Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Unspecified cerebrovascular disease Disc. AE
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Lightheadedness below serious, 11 patient
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Sickness/nausea below serious, 11 patient
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Dry mouth below serious, 3 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Indigestion below serious, 4 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Insomnia below serious, 5 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Soft stools below serious, 5 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Decreased appetite below serious, 6 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Drowsiness below serious, 7 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Social Anxiety Disorder
Population Size: 30
Sources:
Sleep decreased below serious, 10 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Agitation below serious, 5 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Dizziness below serious, 5 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Sweating below serious, 5 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Dry mouth below serious, 7 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Daytime sleepiness below serious, 9 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Headache below serious, 9 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
Nausea below serious, 9 patients
100 mg 1 times / day steady, oral (max)
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 30
Health Status: unhealthy
Condition: Chronic Depression
Population Size: 30
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
weak
likely (co-administration study)
Comment: "coadministration with desipramine showed desipramine increased Cmax 25% and AUC 17% and ""clinical significance of changes in desipramine Cmax is not clear""; desvenlaxafine is not an inhibitor of the CYP P450 isozymes except a possible inhibiton of CYP1A2"
Page: 4, 41
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter.
2007 Nov
Desvenlafaxine and venlafaxine exert minimal in vitro inhibition of human cytochrome P450 and P-glycoprotein activities.
2009
Comparison of the pharmacokinetics of venlafaxine extended release and desvenlafaxine in extensive and poor cytochrome P450 2D6 metabolizers.
2009 Feb
Discontinuation symptoms and taper/poststudy-emergent adverse events with desvenlafaxine treatment for major depressive disorder.
2009 Nov
Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician.
2010 Jan
Desvenlafaxine in the treatment of major depressive disorder.
2011 Dec
Discovery of a potent, dual serotonin and norepinephrine reuptake inhibitor.
2013 Jun 13
Syndrome of inappropriate antidiuretic hormone secretion associated with desvenlafaxine.
2014 Apr
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

Recommended dose: 50 mg once daily with or without food.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:55:18 UTC 2023
Edited
by admin
on Sat Dec 16 08:55:18 UTC 2023
Record UNII
ZG9HEJ3BBR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESVENLAFAXINE BENZOATE
Common Name English
Desvenlafaxine benzoate [WHO-DD]
Common Name English
PHENOL, 4-(2-(DIMETHYLAMINO)-1-(1-HYDROXYCYCLOHEXYL)ETHYL)-, BENZOATE (1:1)
Systematic Name English
Code System Code Type Description
SMS_ID
300000027151
Created by admin on Sat Dec 16 08:55:18 UTC 2023 , Edited by admin on Sat Dec 16 08:55:18 UTC 2023
PRIMARY
CAS
1147940-37-1
Created by admin on Sat Dec 16 08:55:18 UTC 2023 , Edited by admin on Sat Dec 16 08:55:18 UTC 2023
PRIMARY
PUBCHEM
25265778
Created by admin on Sat Dec 16 08:55:18 UTC 2023 , Edited by admin on Sat Dec 16 08:55:18 UTC 2023
PRIMARY
FDA UNII
ZG9HEJ3BBR
Created by admin on Sat Dec 16 08:55:18 UTC 2023 , Edited by admin on Sat Dec 16 08:55:18 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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