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
SMILES
COCCCC\C(C1=CC=C(C=C1)C(F)(F)F)=N/OCCN
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+
DescriptionSources: http://www.drugbank.ca/drugs/DB00176Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/fluvoxamine.html
Sources: http://www.drugbank.ca/drugs/DB00176
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL228 Sources: http://www.drugbank.ca/drugs/DB00176 |
|||
Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26162595 |
7.84 µM [IC50] | ||
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24855828 |
0.29 µM [Ki] | ||
Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21722088 |
13.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LUVOX Approved UseLUVOX 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 Date2007 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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... |
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 |
Other AEs: Abdominal pain, Nausea... |
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%) Sources: Page: p.12Insomnia (4%) Somnolence (4%) Headache (3%) Asthenia (2%) Vomiting (2%) Nervousness (2%) Agitation (2%) Dizziness (2%) |
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 Other AEs:Serotonin syndrome Seizures Hyponatremia Hypomania Sources: Page: p.1 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
|
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 |
|
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 |
|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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). |
|||
Page: 9.0 |
yes | |||
Page: 9.0 |
yes | |||
yes | ||||
Page: 9.0 |
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/fluvoxamine.html
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17920044
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
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000175696
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
||
|
NDF-RT |
N0000000109
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
||
|
NCI_THESAURUS |
C265
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
||
|
WHO-ATC |
N06AB08
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
||
|
LIVERTOX |
NBK548905
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
||
|
WHO-VATC |
QN06AB08
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
||
|
NCI_THESAURUS |
C94725
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
54739-18-3
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
O4L1XPO44W
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
Fluvoxamine
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
5324346
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
5138
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
100000080427
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
FLUVOXAMINE
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
1230
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
42355
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | RxNorm | ||
|
7189
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
D016666
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
SUB07769MIG
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
C61769
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
DB00176
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
CHEMBL814
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
m5516
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | Merck Index | ||
|
DTXSID2044002
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
O4L1XPO44W
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY | |||
|
3879
Created by
admin on Fri Dec 15 15:11:33 GMT 2023 , Edited by admin on Fri Dec 15 15:11:33 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)