FLUVOXAMINE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H21F3N2O2.C4H4O4
Molecular Weight	434.4068
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LFMYNZPAVPMEGP-PIDGMYBPSA-N

InChI=1S/C15H21F3N2O2.C4H4O4/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18;5-3(6)1-2-4(7)8/h5-8H,2-4,9-11,19H2,1H3;1-2H,(H,5,6)(H,7,8)/b20-14+;2-1-

HIDE SMILES / InChI

Description
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	Potency
Serotonin transporter 178 Target ID: CHEMBL228 Sources: http://www.drugbank.ca/drugs/DB00176	Inhibitor 8297
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26162595	Inhibitor 8297	7.84 µM [IC50]
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24855828	Inhibitor 8297	0.29 µM [Ki]
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21722088	Inhibitor 8297	13.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obsessive-compulsive disorder 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021519lbl.pdf	Primary		Approved 8429	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 1.19802246E12

C_max

Value	Dose	Analyte	Population
4.2 ng/mL/kg DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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	Analyte	Population
43.9 ng × h/mL/kg DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
15.6 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/17952747 Page: p.791	unhealthy, 25 n = 1 Health Status: unhealthy Condition: Depression Age Group: 25 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17952747 Page: p.791	Other AEs: Status epilepticus... Other AEs: Status epilepticus Sources: https://pubmed.ncbi.nlm.nih.gov/17952747 Page: p.791
4.8 g single, oral Overdose Dose: 4.8 g Route: oral Route: single Dose: 4.8 g Sources: https://pubmed.ncbi.nlm.nih.gov/7906658 Page: p.203	healthy n = 1 Health Status: healthy Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7906658 Page: p.203	Other AEs: Abdominal pain, Nausea... Other AEs: Abdominal pain Nausea Diarrhoea Sources: https://pubmed.ncbi.nlm.nih.gov/7906658 Page: p.203
300 mg multiple, oral (max) Recommended Dose: 300 mg Route: oral Route: multiple Dose: 300 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf Page: p.12	unhealthy n = 1087 Health Status: unhealthy Condition: Obsessive compulsive disorder\|depression Population Size: 1087 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf Page: p.12
300 mg multiple, oral (max) Recommended Dose: 300 mg Route: oral Route: multiple Dose: 300 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Obsessive compulsive disorder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021519s003lbl.pdf Page: p.1

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 P-gp 1461	P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2D6 1891	inhibitor 3277 Sources: https://link.springer.com/article/10.2165/00003495-200060040-00006	weak
CYP1A2 1692	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529390272X	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). Sources: https://www.sciencedirect.com/science/article/abs/pii/000629529390272X
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021519s012lbl.pdf#page=9 Page: 9.0	yes
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021519s012lbl.pdf#page=9 Page: 9.0	yes
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12649369/	yes
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021519s012lbl.pdf#page=9 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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021519s012lbl.pdf#page=9 Page: 9.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250600718464	yes
P-gp 1537	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3268186/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY114043	https://www.001chemical.com/chem/61718-82-9
3B Scientific (Wuhan) Corp	3B3-052004	http://www.3bsc.com/index/pro_info.php?id=90280
AA Blocks	AA00IAU3	https://www.aablocks.com/goods/Goods/detail?id=AA00IAU3
AHH Chemical co.,ltd	MT-51872	http://www.ahhchemical.com/product/MT-51872.html
AK Scientific, Inc. (AKSCI)	67924	http://www.aksci.com/item_detail.php?cat=67924
AK Scientific, Inc. (AKSCI)	J90043	http://www.aksci.com/item_detail.php?cat=J90043
Aaron Chemicals	AR00IBLV	http://www.aaronchem.com/61718-82-9
Acadechem	ACDC-063925	http://acadechemical.com/product/6021
Achemtek	0104-021333	http://www.achemtek.com/61718-82-9
Alfa Chemistry	AP61718829-A	https://reagents.alfa-chemistry.com/product/fluvoxamine-maleate-cas-61718-82-9-14127.html
Alfa Chemistry	AP61718829-B	https://reagents.alfa-chemistry.com/product/fluvoxamine-maleate-cas-61718-82-9-14128.html
Alsachim	930	http://www.alsachim.com/product-C2839-glo.bal-view.html
Ambeed	A771257	https://www.ambeed.com/products/61718-82-9.html
Ambinter	Amb15691917	http://www.ambinter.com/reference/15691917
Ambinter	Amb2444032	http://www.ambinter.com/reference/2444032
Angene	AGN-PC-0T1FVG	http://www.angenechemical.com/productshow/AGN-PC-0T1FVG.html
Anward	ANW-64083	http://www.anward.com/pro_result/50534
Ark Pharm	AK-51736	http://www.arkpharminc.com/products/61718-82-9.html
Aurora Fine Chemicals LLC	A13.108.176	http://online.aurorafinechemicals.com/info?ID=A13.108.176
Aurum Pharmatech LLC	NE47064	http://www.Aurumpharmatech.com/Product/ProductDetails/NE47064
AvaChem Scientific	2799	http://www.avachem.com/productSearch.asp?2799
BLD Pharm	BD16087	http://www.bldpharm.com/products/61718-82-9.html
BOC Sciences	61718-82-9	https://www.bocsci.com/fluvoxamine-maleate-cas-61718-82-9-item-84-73281.html
BioChemPartner	BCP06470	http://www.biochempartner.com/61718-82-9-BCP06470
BioCrick	BCC1215	http://www.biocrick.com/Fluvoxamine-maleate-BCC1215.html
CSNpharm	CSN12312	https://www.csnpharm.com/products/fluvoxamine-maleate.html
Chem Scene	CS-1839	http://www.chemscene.com/61718-82-9.html
ChemMol	30102974	http://www.chemmol.com/chemmol/30102974.html
ChemMol	44002360	http://www.chemmol.com/chemmol/44002360.html
ChemMol	97900565	http://www.chemmol.com/chemmol/97900565.html
ChemShuttle	151413	http://www.chemshuttle.com/catalogsearch/result/?q=61718-82-9&cat=
Chemenu	CM110029	http://www.chemenu.com/products/CM110029
Chemspace	CSSB00000695070	https://chem-space.com/CSSB00000695070
Chemspace	CSSB00016999329	https://chem-space.com/CSSB00016999329
Chemspace	CSSB00020615146	https://chem-space.com/CSSB00020615146
Chemspace	CSSB00159245923	https://chem-space.com/CSSB00159245923
Clearsynth	CS-O-05780	http://www.clearsynth.com/en/CSO05780.html
Clearsynth	CS-O-06634	http://www.clearsynth.com/en/CSO06634.html
Clearsynth	CS-O-30921	https://www.clearsynth.com/en/CSO30921.html
Combi-Blocks	QH-5087	http://www.combi-blocks.com/cgi-bin/find.cgi?QH-5087
DC Chemicals	DC9139	http://www.dcchemicals.com/product_show-Fluvoxamine_maleate.html
Enamine	Z1583164922	https://www.enaminestore.com/catalog/Z1583164922
Finetech	FT-0626496	http://www.finetechnology-ind.com/prod/detail/pub/61718-82-9.html
Glentham Life Sciences	GP8417	http://www.glentham.com/products/product/GP8417/
Hairui	HR126565	http://www.hairuichem.com/en/product/54739-18-3.html
Hairui	HR100162	http://www.hairuichem.com/en/product/61718-82-9.html
Hello Bio	HB2138	http://www.hellobio.com/fluvoxamine-maleate.html
LGC Standards	MM0058.00	https://www.lgcstandards.com/US/en/p/MM0058.00
Lab Network	LN00193865	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00193865
Matrix Scientific	94691	https://www.matrixscientific.com/094691.html
MedChem Express	HY-B0103A	https://www.medchemexpress.com/Fluvoxamine-maleate.html
MolPort	MolPort-002-885-827	https://www.molport.com/shop/molecule-link/MolPort-002-885-827
MolPort	MolPort-003-666-870	https://www.molport.com/shop/molecule-link/MolPort-003-666-870
MolPort	MolPort-044-175-494	https://www.molport.com/shop/molecule-link/MolPort-044-175-494
MolPort	MolPort-046-682-876	https://www.molport.com/shop/molecule-link/MolPort-046-682-876
Molcore	MC559791	https://www.molcore.com/product/54739-18-3
Molcore	MC114043	https://www.molcore.com/product/61718-82-9
MuseChem	A000443	https://www.musechem.com/product/A000443.html
OChem	6991	http://www.ocheminc.com/index.php?act=psearch&pid=739F183
Oakwood	245750	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=167600&ExtHyperLink=1
Parchem	29005	http://www.parchem.com/chemical-supplier-distributor/Fluvoxamine-Maleate-019005.aspx
Parchem	29006	http://www.parchem.com/chemical-supplier-distributor/Fluvoxamine-Maleate-019006.aspx
Selleck Chemicals	S1336	http://www.selleckchem.com/products/Fluvoxamine-maleate.html
Sigma-Aldrich	F-040_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/f040?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP600_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp600?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1793_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1793?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	F2802_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/f2802?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1285909_USP	https://www.sigmaaldrich.com/catalog/product/usp/1285909?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S528235	http://www.smolecule.com/products/s528235
TCI (Tokyo Chemical Industry)	F0858	http://www.tcichemicals.com/eshop/en/us/commodity/F0858/index.html
THE BioTek	bt-268456	https://www.thebiotek.com/product/inhibitors/bt-268456
Tocris	1033	https://www.tocris.com/products/fluvoxamine-maleate_1033
VladaChem	VL272732-1G	https://www.vladachem.com/product.php?products=61718-82-9
abcr GmbH	AB505781	http://www.abcr.de/shop/en/AB505781
iChemical	EBD19367	http://www.ichemical.com/chemicals/cas-61718-82-9
mcule	MCULE-4841680762	https://mcule.com/MCULE-4841680762/

PubMed

Title	Date	PubMed
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.	1997 Dec 11	9537821
Pharmacological characterization and visualization of the glial serotonin transporter.	2001 Jul	11311448
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942

Patents

Sample Use Guides

In Vivo Use Guide

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

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

FLUVOXAMINE MALEATE

Official Name

English

FLUVOXAMINE MALEATE [EP MONOGRAPH]

Common Name

English

FLUVOXAMINE MALEATE [MART.]

Common Name

English

FLUVOXAMINE MALEATE [VANDF]

Common Name

English

FLUVOXAMINE MALEATE [MI]

Common Name

English

NSC-759602

Code

English

FLUVOXAMINE MALEATE [USAN]

Common Name

English

FLUVOXAMINE MALEATE [ORANGE BOOK]

Common Name

English

FEVARIN

Brand Name

English

FLUVOXAMINE MALEATE [USP MONOGRAPH]

Common Name

English

DU-23000

Code

English

FAVERIN

Brand Name

English

5-METHOXY-4'-(TRIFLUOROMETHYL)VALEROPHENONE-(E)-O-(2-AMINOETHYL)OXIME MALEATE (1:1)

Systematic Name

English

1-PENTANONE, 5-METHOXY-1-(4-(TRIFLUOROMETHYL)PHENYL)-, O-(2-AMINOETHYL)OXIME, (E)-, (Z)-2-BUTENEDIOATE (1:1)

Common Name

English

DU23000

Code

English

LUVOX

Brand Name

English

Fluvoxamine maleate [WHO-DD]

Common Name

English

FLUVOXAMINE MALEATE [USP-RS]

Common Name

English

FLUVOXAMINE MALEATE [JAN]

Common Name

English

FLUVOXAMINE HYDROGENMALEATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C94725