CHEBI:9123 - sertraline

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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 0
Average Mass 306.23000
Monoisotopic Mass 305.074
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.
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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
INNs Sources
sertralina ChemIDplus
sertraline ChemIDplus
sertralinum ChemIDplus
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
Manual Xrefs Databases
2436 DrugCentral
C07246 KEGG COMPOUND
D02360 KEGG DRUG
DB01104 DrugBank
HMDB0005010 HMDB
LSM-3843 LINCS
Sertraline Wikipedia
SRE PDBeChem
US4536518 Patent
View more database links
Registry Numbers Types Sources
5753709 Reaxys Registry Number Reaxys
5753709 Beilstein Registry Number ChemIDplus
79617-96-2 CAS Registry Number ChemIDplus
79617-96-2 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
19502000 PubMed citation Europe PMC
21823671 PubMed citation Europe PMC
Last Modified
22 February 2017