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Drug

D0471 | sertraline

Molecular Formula C17H17Cl2N
Molecular Weight 306.2
Structure
State solid
Route of elimination Sertraline and its metabolites are excreted via both renal and fecal elimination. In a study of radiolabeled sertraline involving two healthy male subjects, about 40-45% of total radioactivity was observed in 9 days post-administration [FDA Label] with negligible amount (<0.2%) of unchanged parent compound detected [L1373]. For the same period, 40-45% of total radioactivity was also accounted for in feces, where 12-14% of the radioactivity was unchanged sertraline [FDA Label].
Protein binding In vitro protein binding studies indicate that sertraline is highly bound to serum proteins (98%) in the range of 20 to 500 ng/mL [FDA Label], predominantly to albumin and &alpha;<sub>1</sub>-acid glycoprotein [A1846].
Half life The elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours [FDA Label].
Absorption Following once-daily administration over the range of 50 to 200 mg for 14 days, mean peak plasma concentrations (Cmax) of sertraline occurred between 4.5 to 8.4 hours post-administration [FDA Label]. The steady-state concentrations are reached after 1 week following once-daily administration, and approximately two-fold accumulation up to steady-state concentrations is observed [FDA Label]. The single dose bioavailability of sertraline tablets is approximately equal to an equivalent dose of sertraline oral solution [FDA Label]. The effects of food on the bioavailability of the sertraline tablet and oral concentrate were studied in subjects administered a single dose with and without food. For the tablet, AUC was slightly increased when drug was administered with food but the Cmax was 25% greater, while the time to reach peak plasma concentration (Tmax) decreased from 8 hours post-dosing to 5.5 hours. For the oral concentrate, Tmax was slightly prolonged from 5.9 hours to 7.0 hours with food.
Trade names Zoloft
Description antidepressant; a selective serotonin reuptake inhibitor (SSRI)

N

N06AB06 Sertraline


[N06AB] Selective serotonin reuptake inhibitors


[N06A] ANTIDEPRESSANTS


[N06] PSYCHOANALEPTICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
RESPIRATION decrease 307
ELECTRON TRANSPORT CHAIN decrease 48
ELECTRON TRANSPORT CHAIN rat brain mitochondria decrease 307
ELECTRON TRANSPORT CHAIN rat liver mitochondria decrease 307
GLUCOSE GALACTOSE IC50 RATIO 30.7 ± 4.7, 24.7 ± 16.0, 1.2, 29.1 ± 12.0, 23.6 ± 19.2, 1.2 4hr H9c2 cells high-glucose–galactose cell viability assay with JC-1 mitochondrial membrane potential and ATP-depletion assays (CellTiter-Glo reagent ). glucose/galactose IC50 ratio (JC-1 IC50 in glucose, JC-1 IC50 in galactose, JC-1 glu/gla, ATP IC50 in glucose, ATP IC50 in galactose, ATP glu/gla ) 50
SHAPE Change 307
BIOGENESIS decrease 307

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase inhibitor 48
NADH:ubiquinone reductase Inhibition 307
Quinol--cytochrome-c reductase Inhibition 307
Cytochrome c oxidase Inhibition 307
Caspase-3 increase 307

Organism Test type Route Dose (normalized dose) Effect Source
women TDLo oral 7mg/kg/2W-I (7mg/kg) Journal of Clinical Psychiatry. Vol. 54, Pg. 432, 1993.
women TDLo oral 7mg/kg/7D-I (7mg/kg) behavioral: excitement Journal of Clinical Psychiatry. Vol. 54, Pg. 321, 1993.
man TDLo oral 2857ug/kg (2.857mg/kg) Shinkei Seishin Yakuri. Neuropsychopharmacology. Vol. 19, Pg. 395, 1997.
mouse LDLo oral 336mg/kg (336mg/kg) Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
rat LDLo intraperitoneal 56mg/kg (56mg/kg) Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
mouse LDLo intraperitoneal 56mg/kg (56mg/kg) Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
rat LDLo oral 840mg/kg (840mg/kg) Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.


  • (+)-Sertraline (+)-Sertraline (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
    (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride (1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-tetralin-1-amine (1S,4S)-sertraline
    (1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine (1S-cis)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-naphthalenamine
    1-Naphthalenamine, 1,2,3,4-tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-, (1S-cis)- 1-Naphthalenamine, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, (1S,4S)- 1-Naphthalenamine,1,2,3,4-tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-, (1S-cis)-
    617S962 79617-96-2 A839725
    AB00514002 AB00514002_17 AB00514002_18
    AB1004870 AC-15639 AKOS016842914
    ANW-58187 API0004164 AX8034967
    BDBM50028094 BDBM79021 BIDD:GT0768
    BIDD:PXR0193 BPBio1_001285 BRD-K82036761-003-02-1
    BRD-K82036761-003-07-0 BRD-K82036761-003-20-3 BRN 5753709
    BSPBio_001167 BSPBio_002698 C-19042
    C-4401 C07246 C17H17Cl2N
    CC-34407 CCG-221014 CHEBI:9123
    CHEMBL809 CP-519741 CTK8B7684
    Cp 51974 D02360 DB01104
    DTXSID6023577 EN300-150167 FT-0081122
    FT-0630872 GTPL4798 HMS2098K09
    HMS2231I09 HMS3715K09 HSDB 7037
    KBio3_001918 KBioGR_001724 LS-94179
    Lustral MCULE-4360779618 MLS001195647
    MLS001401398 MLS002222308 NCGC00092386
    NCGC00092386-03 NCGC00092386-04 NCGC00092386-05
    NCGC00092386-06 NCGC00092386-07 NCGC00092386-08
    NCGC00092386-09 NCGC00092386-10 Prestwick3_001014
    PubChem5865 Q407617 QUC7NX6WMB
    REGID_for_CID_68617 SBI-0206734.P001 SC-16114
    SCHEMBL28701 SMR000466298 SMR000596516
    SPBio_000385 SR-01000759296 SR-01000759296-5
    SRE Sertralina Sertralina [Spanish]
    Sertraline (INN) Sertraline [INN:BAN] Sertraline [Zoloft]
    Sertraline; Sertralinum Sertralinum [Latin]
    Spectrum2_000493 Spectrum3_001079 Spectrum4_001232
    TBA-2010_Sertraline_1 TR-025284 UNII-QUC7NX6WMB
    VGKDLMBJGBXTGI-SJCJKPOMSA-N ZINC1853550 Zoloft
    [(1S,4S)-4-(3,4-dichlorophenyl)tetralin-1-yl]-methyl-amine;hydrochloride cid_63009 cis-(+)-sertraline
    cp-51974 sertraline sertraline (Zoloft)
    syn-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

    DrugBank Name sertraline
    DrugBank DB01104
    CAS Number 219736-80-8, 79559-97-0, 79617-95-1, 79617-96-2
    PubChem Compound 68617
    KEGG Compound ID C07246
    KEGG Drug D02360
    ChEBI 9123
    PharmGKB PA451333