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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17Cl2N
Molecular Weight 306.23
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SERTRALINE, CIS-(-)-

SMILES

CN[C@@H]1CC[C@H](C2=CC(Cl)=C(Cl)C=C2)C3=C1C=CC=C3

InChI

InChIKey=VGKDLMBJGBXTGI-SJKOYZFVSA-N
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-/m1/s1

HIDE SMILES / InChI
cis-(-)-Sertraline (aka 1R,4R-sertraline) is the therapeutically inactive enantiomer of Sertraline. Sertraline has four stereoisomers: (1R,4R), (1S,4S), (1R,4S), and (1S,4R), of which the (1S,4S) isomer is the active therapeutic compound. Sertraline is sold under the brand name Zoloft (and others) as an anti-depressant acting as a selective serotonin reuptake inhibitor. The bio-activity of sertraline is restricted to (1S,4S), and (1R,4R), where (1S,4S) is most potent.

Originator

Curator's Comment: # Pfizer Inc.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Analysis of cis-trans isomers and enantiomers of sertraline by cyclodextrin-modified micellar electrokinetic chromatography.
2000 Feb 25
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
SERTRALINE, CIS-(-)-
Common Name English
SERTRALINE, (1R,4R)-
Common Name English
1-NAPHTHALENAMINE, 4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-METHYL-, (1R-CIS)-
Systematic Name English
(1R,4R)-4-(3,4-DICHLOROPHENYL)-N-METHYL-1,2,3,4-TETRAHYDRONAPHTHALEN-1-AMINE
Systematic Name English
CP-51973
Code English
1-NAPHTHALENAMINE, 4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-METHYL-, (1R,4R)-
Systematic Name English
SERTRALINE HYDROCHLORIDE IMPURITY, (R,R) SERTRALINE-
Common Name English
SERTRALINE HYDROCHLORIDE IMPURITY G [EP IMPURITY]
Common Name English
SERTRALINE ENANTIOMER
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID401036448
Created by admin on Sat Dec 16 07:58:29 GMT 2023 , Edited by admin on Sat Dec 16 07:58:29 GMT 2023
PRIMARY
CAS
79617-98-4
Created by admin on Sat Dec 16 07:58:29 GMT 2023 , Edited by admin on Sat Dec 16 07:58:29 GMT 2023
PRIMARY
PUBCHEM
54375
Created by admin on Sat Dec 16 07:58:29 GMT 2023 , Edited by admin on Sat Dec 16 07:58:29 GMT 2023
PRIMARY
FDA UNII
CVO48CMI7U
Created by admin on Sat Dec 16 07:58:29 GMT 2023 , Edited by admin on Sat Dec 16 07:58:29 GMT 2023
PRIMARY