U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

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

SHOW SMILES / InChI
Structure of SERTRALINE

SMILES

CN[C@H]1CC[C@@H](C2=CC=C(Cl)C(Cl)=C2)C3=CC=CC=C13

InChI

InChIKey=VGKDLMBJGBXTGI-SJCJKPOMSA-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-/m0/s1

HIDE SMILES / InChI

Description

Sertraline (trade names Zoloft and others) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. Sertraline is primarily prescribed for major depressive disorder in adult outpatients as well as obsessive-compulsive disorder, panic disorder, and social anxiety disorder, in both adults and children. The exact mechanism of action sertraline is not fully known, but the drug appears to selectively inhibit the reuptake of serotonin at the presynaptic membrane. This results in an increased synaptic concentration of serotonin in the CNS, which leads to numerous functional changes associated with enhanced serotonergic neurotransmission. It is suggested that these modifications are responsible for the antidepressant action observed during long-term administration of antidepressants. It has also been hypothesized that obsessive-compulsive disorder is caused by the dysregulation of serotonin, as it is treated by sertraline, and the drug corrects this imbalance. Compared to other SSRIs, sertraline tends to be associated with a higher rate of psychiatric side effects and diarrhea. It tends to be more activating (that is, associated with a higher rate of anxiety, agitation, insomnia, etc.) than other SSRIs, aside from fluoxetine. Over a two-week treatment of healthy volunteers, sertraline slightly improved verbal fluency but did not affect word learning, short-term memory, vigilance, flicker fusion time, choice reaction time, memory span, or psychomotor coordination. In spite of lower subjective rating, that is, feeling that they performed worse, no clinically relevant differences were observed in the objective cognitive performance in a group of people treated for depression with sertraline for 1.5 years as compared to healthy controls

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.0 nM [IC50]
825.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZOLOFT
Primary
ZOLOFT
Primary
ZOLOFT
Primary
ZOLOFT
Primary
ZOLOFT
Primary
ZOLOFT

Cmax

ValueDoseCo-administeredAnalytePopulation
20.6 μg/L
100 mg single, oral
SERTRALINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
546 μg × h/L
100 mg single, oral
SERTRALINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
25.4 h
100 mg single, oral
SERTRALINE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Initial: 50 mg PO qDay May increase by 25 mg at 1-week intervals; not to exceed 200 mg qDay
Route of Administration: Oral
In Vitro Use Guide
Human endometrial tissue was obtained from healthy 25–35 year donors at Tehran University of Medical Sciences, Tehran. CD146+, CD90+, and CD105+ cells were isolated from total cells by fluorescent analyzer cell sorting (FACS). After 10 days (d) in culture, expanded cell populations were transferred into a medium consisting of DMEM (Gibco- BRL) containing 10% FBS and 25 mkg/mL gentamicin (Sigma, USA). The cells were pre-treated with di-methyl sulfoxide (DMSO, Sigma) and exposed to 10^6 M all-trans RA (retinoic acid) (Sigma, USA) for 7 d. RA diluted in absolute ethanol was added to the culture medium twice a week. These cells were also treated with sertraline (0, 5, and 10 mkM, Sigma, USA). Cells were harvested for RT-PCR or Western blotting on days 0, 7, 14, and 21 of RA and sertraline treatment. Immunocytochemistry was carried out with cells collected on day 15 after RA and sertraline treatment.