sertraline (CHEBI:9123)

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ChEBI Name	sertraline

ChEBI ID	CHEBI:9123

Definition	A member of the class of tetralins that is tetralin which is substituted at positions 1 and 4 by a methylamino and a 3,4-dichlorophenyl group, respectively (the S,S diastereoisomer). A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as the hydrochloride salt as an antidepressant for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic stress disorder.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C17H17Cl2N

Net Charge

Average Mass

306.23000

Monoisotopic Mass

305.07380

InChI

InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1

InChIKey

VGKDLMBJGBXTGI-SJCJKPOMSA-N

SMILES

[H][C@]1(CC[C@H](NC)c2ccccc12)c1ccc(Cl)c(Cl)c1

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	serotonin uptake inhibitor A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.

Application(s):	serotonin uptake inhibitor A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent. antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.

ChEBI Ontology
Outgoing	sertraline (CHEBI:9123) has parent hydride tetralin (CHEBI:35008) sertraline (CHEBI:9123) has role antidepressant (CHEBI:35469) sertraline (CHEBI:9123) has role serotonin uptake inhibitor (CHEBI:50949) sertraline (CHEBI:9123) is a dichlorobenzene (CHEBI:23697) sertraline (CHEBI:9123) is a secondary amino compound (CHEBI:50995) sertraline (CHEBI:9123) is a tetralins (CHEBI:36786) sertraline (CHEBI:9123) is conjugate base of sertraline(1+) (CHEBI:64214)

Incoming	sertraline(1+) (CHEBI:64214) is conjugate acid of sertraline (CHEBI:9123)

IUPAC Name

(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

Synonyms	Sources
(+)-sertraline	ChEBI
(1S,4S)-sertraline	ChemIDplus
(1S-cis)-1,2,3,4-tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine	ChemIDplus
cis-(+)-sertraline	ChEBI
CP 51974	NIST Chemistry WebBook
Sertraline	KEGG COMPOUND

Last Modified

22 February 2017