ContaminantDB: Fluvoxamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (36)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:13 UTC

Update Date

2026-05-14 16:24:29 UTC

Accession Number

CHEM002137

Identification

Common Name

Fluvoxamine

Class

Small Molecule

Description

Fluvoxamine is an exogenous solid with the formula C15H21F3N2O2 and an average molecular weight of 318.33 g/mol. Fluvoxamine belongs to the trifluoromethylbenzenes, a subclass of benzene and substituted derivatives within the organic compounds. It is utilized as an antidepressant, an anxiolytic drug, and a biological serotonin uptake inhibitor. Recorded exposure routes for the compound include oral administration. It has been identified in seven recorded sources, including antidepressants within healthcare, pharmaceuticals, and veterinary products; drinking water and water supply; household cleaning and consumer products such as other smoking requisites and non-electric simulated smoking devices; and electrical and electronic equipment, specifically magnets, relays, and electric hearing aids. The compound interacts with eight recorded protein targets, including the sodium-dependent serotonin transporter (SLC6A4), 5-hydroxytryptamine receptor 1A (HTR1A), 5-hydroxytryptamine receptor 2A (HTR2A), muscarinic acetylcholine receptor M1 (CHRM1), cytochrome P450 2C9 (CYP2C9), sodium-dependent noradrenaline transporter (SLC6A2), and sodium-dependent dopamine transporter (SLC6A3). The antidepressant, antiobsessive-compulsive, and antibulimic actions of fluvoxamine are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. It blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, which enhances the actions of serotonin on 5HT1A autoreceptors. Furthermore, SSRIs bind with significantly less affinity to norepinephrine, acetylcholine, and histamine receptors than tricyclic antidepressant drugs.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Anxiety Agent
Antidepressant
Antidepressant, Second-Generation
Antidepressive Agent, Second-Generation
Drug
Ether
Metabolite
Organic Compound
Organofluoride
Selective Serotonin Reuptake Inhibitor
Serotonin Uptake Inhibitor
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Fluvoxamina	ChEBI
Fluvoxaminum	ChEBI
Aliud brand OF fluvoxamine maleate	MeSH
Fluvoxamin neuraxpharm	MeSH
Geminis, fluvoxamina	MeSH
Ratiopharm brand OF fluvoxamine maleate	MeSH
Fluvoxamin stada	MeSH
Fluvoxamine	MeSH
Novopharm brand OF fluvoxamine maleate	MeSH
Nu fluvoxamine	MeSH
Stadapharm brand OF fluvoxamine maleate	MeSH
Neuraxpharm brand OF fluvoxamine maleate	MeSH
Faverin	MeSH
Fluvoxamin al	MeSH
Fluvoxamin ratiopharm	MeSH
Fluvoxamin-neuraxpharm	MeSH
Fluvoxamine, (Z)-isomer	MeSH
novo-Fluvoxamine	MeSH
Nu pharm brand OF fluvoxamine maleate	MeSH
Nu-fluvoxamine	MeSH
Declimed brand OF fluvoxamine maleate	MeSH
PMS Fluvoxamine	MeSH
Floxyfral	MeSH
Fluvoxamine maleate	MeSH
Pharmascience brand OF fluvoxamine maleate	MeSH
Desiflu	MeSH
Dumirox	MeSH
Fluvoxadura	MeSH
Fluvoxamin beta	MeSH
Fluvoxamin-ratiopharm	MeSH
Geminis brand OF fluvoxamine maleate	MeSH
Luvox	MeSH
Solvay brand OF fluvoxamine maleate	MeSH
Fevarin	MeSH
Fluvoxamina geminis	MeSH
Fluvoxamine maleate, (e)-isomer	MeSH
Merck dura brand OF fluvoxamine maleate	MeSH
Nu-pharm brand OF fluvoxamine maleate	MeSH
Betapharm brand OF fluvoxamine maleate	MeSH
novo Fluvoxamine	MeSH
PMS-Fluvoxamine	MeSH
ratio Fluvoxamine	MeSH
ratio-Fluvoxamine	MeSH

Chemical Formula

C₁₅H₂₁F₃N₂O₂

Average Molecular Mass

318.335 g/mol

Monoisotopic Mass

318.156 g/mol

CAS Registry Number

54739-18-3

IUPAC Name

(E)-(2-aminoethoxy)({5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene})amine

Traditional Name

fluvoxamine

SMILES

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

InChI Identifier

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+

InChI Key

InChIKey=CJOFXWAVKWHTFT-XSFVSMFZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Dialkyl ether
Ether
Alkyl fluoride
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Amine
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

(trifluoromethyl)benzenes (CHEBI:5138 )
5-methoxyvalerophenone O-(2-aminoethyl)oxime (CHEBI:5138 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Fluvoxamine Mechanism of Action Action Pathway New	SMP0126511	Not Available
Fluvoxamine Drug Metabolism Action Pathway	SMP0142639	Not Available

Applications

Biological Roles

serotonin uptake inhibitor

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	120-121.5°C
Boiling Point	Not Available
Solubility	7.34e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.8	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.84 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	79.2 m³·mol⁻¹	ChemAxon
Polarizability	32.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-4097000000-bd73d7b04a9cbd6e10a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-7191000000-b8ff0c1ca5bbe3302bf6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01vx-9260000000-61d88b8b55778271c507	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1049000000-16bb56f2edbb8d418047	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1191000000-aa43007dad9f770e769d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvl-9260000000-8b12b73c65cee8c561ed	Spectrum

Toxicity Profile

Route of Exposure

Oral. Well absorbed, bioavailability of fluvoxamine maleate is 53%.

Mechanism of Toxicity

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 5HT_1A 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 alpha₁- or alpha₂-adrenergic, beta-adrenergic, muscarinic, dopamine D₂, histamine H₁, GABA-benzodiazepine, opiate, 5-HT₁, or 5-HT₂ receptors.

Metabolism

Hepatic Route of Elimination: The main human metabolite was fluvoxamine acid which, together with its N-acetylated analog, accounted for about 60% of the urinary excretion products. Approximately 2% of fluvoxamine was excreted in urine unchanged. Following a 14C-labelled oral dose of fluvoxamine maleate (5 mg), an average of 94% of drug-related products was recovered in the urine within 71 hours. Half Life: 15.6 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For management of depression and for Obsessive Compulsive Disorder (OCD). Has also been used in the management of bulimia nervosa.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Side effects include anorexia, constipation, dry mouth, headache, nausea, nervousness, skin rash, sleep problems, somnolence, liver toxicity, mania, increase urination, seizures, sweating increase, tremors, or Tourette's syndrome.

Treatment

Treatment should consist of those general measures employed in the management of overdosage with any antidepressant. Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large-bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion, or in symptomatic patients. Activated charcoal should be administered. Due to the large volume of distribution of this drug, forced diuresis, dialysis, hemoperfusion and exchange transfusion are unlikely to be of benefit. No specific antidotes for fluvoxamine are known. (4)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Fluvoxamine

Chemspider ID

Not Available

ChEBI ID

5138

PubChem Compound ID

5324346

Kegg Compound ID

C07571

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Welle, H.B.A. and Claassen, V.; U.S. Patent 4,085,225; April 18, 1978; assigned to U.S. Phillips Corp.

MSDS

Link

General References

Not Available

Fluvoxamine (CHEM002137)

Structure for CHEM002137: Fluvoxamine