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Details

Stereochemistry ACHIRAL
Molecular Formula C15H21F3N2O2
Molecular Weight 318.3346
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FLUVOXAMINE, (Z)-

SMILES

COCCCC\C(=N\OCCN)C1=CC=C(C=C1)C(F)(F)F

InChI

InChIKey=CJOFXWAVKWHTFT-ZHZULCJRSA-N
InChI=1S/C15H21F3N2O2/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18/h5-8H,2-4,9-11,19H2,1H3/b20-14-

HIDE SMILES / InChI

Molecular Formula C15H21F3N2O2
Molecular Weight 318.3346
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/fluvoxamine.html

Fluvoxamine is an antidepressant which functions pharmacologically as a selective serotonin reuptake inhibitor. Though it is in the same class as other SSRI drugs, it is most often used to treat obsessive-compulsive disorder. Fluvoxamine has been in use in clinical practice since 1983 and has a clinical trial database comprised of approximately 35,000 patients. It was launched in the US in December 1994 and in Japan in June 1999. As of the end of 1995, more than 10 million patients worldwide have been treated with fluvoxamine. The exact mechanism of action of fluvoxamine has not been fully determined, but appears to be linked to its inhibition of CNS neuronal uptake of serotonin. Fluvoxamine blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. In-vitro studies suggest that fluvoxamine is more potent than clomipramine, fluoxetine, and desipramine as a serotonin-reuptake inhibitor. Studies have also demonstrated that fluvoxamine has virtually no affinity for α1- or α2-adrenergic, β-adrenergic, muscarinic, dopamine D2, histamine H1, GABA-benzodiazepine, opiate, 5-HT1, or 5-HT2 receptors. Fluvoxamine is used for management of depression and for Obsessive Compulsive Disorder (OCD). Has also been used in the management of bulimia nervosa. Fluvoxamine is known under the brand names: Faverin, Fevarin, Floxyfral, Dumyrox and Luvox.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.84 µM [IC50]
0.29 µM [Ki]
13.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LUVOX

Approved Use

LUVOX Tablets are indicated for the treatment of obsessions and compulsions in patients with obsessive compulsive disorder (OCD), as defined in the DSM-III-R.

Launch Date

2007
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.2 ng/mL/kg
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
5.7 ng/mL/kg
150 mg 2 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
14.8 ng/mL/kg
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
43.9 ng × h/mL/kg
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
59.4 ng × h/mL/kg
150 mg 2 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
155.1 ng × h/mL/kg
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.6 h
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUVOXAMINE MALEATE plasma
Homo sapiens
population: UNHEALTHY
age: ADOLESCENT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
9.6 g single, oral
Overdose
Dose: 9.6 g
Route: oral
Route: single
Dose: 9.6 g
Sources: Page: p.791
unhealthy, 25
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 25
Sex: F
Population Size: 1
Sources: Page: p.791
Other AEs: Status epilepticus...
Other AEs:
Status epilepticus
Sources: Page: p.791
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources: Page: p.203
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.203
Other AEs: Abdominal pain, Nausea...
Other AEs:
Abdominal pain
Nausea
Diarrhoea
Sources: Page: p.203
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Disc. AE: Nausea, Insomnia...
AEs leading to
discontinuation/dose reduction:
Nausea (9%)
Insomnia (4%)
Somnolence (4%)
Headache (3%)
Asthenia (2%)
Vomiting (2%)
Nervousness (2%)
Agitation (2%)
Dizziness (2%)
Sources: Page: p.12
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Obsessive compulsive disorder
Sources: Page: p.1
Disc. AE: Suicidal ideation, Serotonin syndrome...
Other AEs: Hypomania...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Serotonin syndrome
Seizures
Hyponatremia
Other AEs:
Hypomania
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Status epilepticus
9.6 g single, oral
Overdose
Dose: 9.6 g
Route: oral
Route: single
Dose: 9.6 g
Sources: Page: p.791
unhealthy, 25
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 25
Sex: F
Population Size: 1
Sources: Page: p.791
Abdominal pain
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources: Page: p.203
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.203
Diarrhoea
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources: Page: p.203
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.203
Nausea
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources: Page: p.203
healthy
n = 1
Health Status: healthy
Population Size: 1
Sources: Page: p.203
Agitation 2%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Asthenia 2%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Dizziness 2%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Nervousness 2%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Vomiting 2%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Headache 3%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Insomnia 4%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Somnolence 4%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Nausea 9%
Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.12
unhealthy
n = 1087
Health Status: unhealthy
Condition: Obsessive compulsive disorder|depression
Population Size: 1087
Sources: Page: p.12
Hypomania
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Obsessive compulsive disorder
Sources: Page: p.1
Hyponatremia Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Obsessive compulsive disorder
Sources: Page: p.1
Seizures Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Obsessive compulsive disorder
Sources: Page: p.1
Serotonin syndrome Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Obsessive compulsive disorder
Sources: Page: p.1
Suicidal ideation Disc. AE
300 mg multiple, oral (max)
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Obsessive compulsive disorder
Sources: Page: p.1
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak
yes [Ki 0.12 uM]
yes (co-administration study)
Comment: The effect of fluvoxamine (100 mg daily for 4 days) on the pharmacokinetics and pharmacodynamics of a single 4 mg dose of tizanidine has been studied in 10 healthy male subjects. Tizanidine Cmax was increased approximately 12-fold (range 5- fold to 32-fold), elimination half-life was increased by almost 3-fold, and AUC increased 33-fold (range 14- fold to 103-fold).
yes
yes
yes
yes
yes (co-administration study)
Comment: . In a pharmacokinetic study, 40 healthy female subjects received fluvoxamine in escalating doses from 50 mg to 200 mg a day for 16 days, with coadministration of alosetron 1 mg on the last day. Fluvoxamine increased mean alosetron plasma concentration (AUC) approximately 6-fold and prolonged the half-life by approximately 3-fold.
Page: 9.0
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
1997 Dec 11
Pharmacological characterization and visualization of the glial serotonin transporter.
2001 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Patents

Sample Use Guides

Usual Adult Dose for Obsessive Compulsive Disorder Initial extended release capsule dose: 100 mg orally once a day at bedtime Initial immediate release tablet dose: 50 mg orally once a day at bedtime Maintenance dose: 100 to 300 mg orally per day. The dose may be increased in 50 mg increments every 4 to 7 days, as tolerated, until maximum therapeutic benefit is achieved. Maximum Dose: 300 mg orally per day
Route of Administration: Oral
In the presence of 100 uM fluvoxamine, Kir4.1 currents heterologously expressed in HEK293T cells gradually increased during a hyperpolarizing step to −110 mV, and the outward current decreased rapidly during a depolarizing step to +30 mV
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:27:18 GMT 2023
Edited
by admin
on Sat Dec 16 05:27:18 GMT 2023
Record UNII
4E72PH61HL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUVOXAMINE, (Z)-
Common Name English
FLUVOXAMINE MALEATE IMPURITY, Z-ISOMER- [USP IMPURITY]
Common Name English
1-PENTANONE, 5-METHOXY-1-(4-(TRIFLUOROMETHYL)PHENYL)-, O-(2-AMINOETHYL)OXIME, (1Z)-
Common Name English
FLUVOXAMINE MALEATE IMPURITY B [EP IMPURITY]
Common Name English
2-((((1Z)-5-METHOXY-1-(4-(TRIFLUOROMETHYL)PHENYL)PENTYLIDENE)AMINO)OXY)ETHANAMINE
Systematic Name English
(Z) FLUVOXAMINE
Common Name English
Code System Code Type Description
CAS
89035-92-7
Created by admin on Sat Dec 16 05:27:18 GMT 2023 , Edited by admin on Sat Dec 16 05:27:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID60237496
Created by admin on Sat Dec 16 05:27:18 GMT 2023 , Edited by admin on Sat Dec 16 05:27:18 GMT 2023
PRIMARY
PUBCHEM
5361192
Created by admin on Sat Dec 16 05:27:18 GMT 2023 , Edited by admin on Sat Dec 16 05:27:18 GMT 2023
PRIMARY
FDA UNII
4E72PH61HL
Created by admin on Sat Dec 16 05:27:18 GMT 2023 , Edited by admin on Sat Dec 16 05:27:18 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP