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

Details

Stereochemistry ACHIRAL
Molecular Formula C15H21F3N2O2
Molecular Weight 318.3352
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FLUVOXAMINE

SMILES

COCCCC/C(=N\OCCN)/c1ccc(cc1)C(F)(F)F

InChI

InChIKey=CJOFXWAVKWHTFT-XSFVSMFZSA-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 318.3352
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment:: 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
7.83999999999999986 µM [IC50]
0.28999999999999998 µM [Ki]
13.4000000000000004 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

1198022400000
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:
unhealthy, 25
Health Status: unhealthy
Age Group: 25
Sex: F
Sources:
Other AEs: Status epilepticus...
Other AEs:
Status epilepticus
Sources:
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources:
healthy
Health Status: healthy
Sources:
Other AEs: Abdominal pain, Nausea...
Other AEs:
Abdominal pain
Nausea
Diarrhoea
Sources:
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
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:
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
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:
AEs

AEs

AESignificanceDosePopulation
Status epilepticus
9.6 g single, oral
Overdose
Dose: 9.6 g
Route: oral
Route: single
Dose: 9.6 g
Sources:
unhealthy, 25
Health Status: unhealthy
Age Group: 25
Sex: F
Sources:
Abdominal pain
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources:
healthy
Health Status: healthy
Sources:
Diarrhoea
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources:
healthy
Health Status: healthy
Sources:
Nausea
4.8 g single, oral
Overdose
Dose: 4.8 g
Route: oral
Route: single
Dose: 4.8 g
Sources:
healthy
Health Status: healthy
Sources:
Agitation 2%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Asthenia 2%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Dizziness 2%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Nervousness 2%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Vomiting 2%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Headache 3%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Insomnia 4%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Somnolence 4%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Nausea 9%
Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Hypomania
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Hyponatremia Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Seizures Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Serotonin syndrome Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
Suicidal ideation Disc. AE
300 mg multiple, oral
Recommended
Dose: 300 mg
Route: oral
Route: multiple
Dose: 300 mg
Sources:
unhealthy
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
Drug as victim
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
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 Jun 26 14:59:58 UTC 2021
Edited
by admin
on Sat Jun 26 14:59:58 UTC 2021
Record UNII
O4L1XPO44W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUVOXAMINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
FLUVOXAMINE [INN]
Common Name English
5-METHOXY-4'-(TRIFLUOROMETHYL)VALEROPHENONE (E)-O-(2-AMINOETHYL)OXIME
Systematic Name English
FLUVOXAMINE [WHO-DD]
Common Name English
1-PENTANONE, 5-METHOXY-1-(4-(TRIFLUOROMETHYL)PHENYL)-, O-(2-AMINOETHYL)OXIME, (1E)-
Systematic Name English
FLUVOXAMINE [VANDF]
Common Name English
FLUVOXAMINE [MI]
Common Name English
N06AB08
Code English
Classification Tree Code System Code
NDF-RT N0000175696
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
NDF-RT N0000000109
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
NCI_THESAURUS C265
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
WHO-ATC N06AB08
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
LIVERTOX 431
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
WHO-VATC QN06AB08
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
NCI_THESAURUS C94725
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
Code System Code Type Description
CAS
54739-18-3
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
LACTMED
Fluvoxamine
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
PUBCHEM
5324346
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
WIKIPEDIA
FLUVOXAMINE
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
DRUG CENTRAL
1230
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
RXCUI
42355
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY RxNorm
IUPHAR
7189
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
MESH
D016666
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
EVMPD
SUB07769MIG
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
NCI_THESAURUS
C61769
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
DRUG BANK
DB00176
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL814
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
MERCK INDEX
M5516
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY Merck Index
EPA CompTox
54739-18-3
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
FDA UNII
O4L1XPO44W
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
INN
3879
Created by admin on Sat Jun 26 14:59:59 UTC 2021 , Edited by admin on Sat Jun 26 14:59:59 UTC 2021
PRIMARY
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