Sertraline (CHEM002346)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (12)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:22 UTC
Update Date2026-05-14 16:57:51 UTC
Accession NumberCHEM002346
Identification
Common NameSertraline
ClassSmall Molecule
DescriptionSertraline hydrochloride belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache (see Toxicity section below for a more detailed listing of side effects). Compared to other agents in this class, sertraline may cause greater diarrheal and male sexual dysfunction effects. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Sertraline may be used to treat major depressive disorder, obsessive-compulsive disorder (OCD), panic disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD) and social anxiety disorder (social phobia).
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antidepressant
  • Antidepressive Agent
  • Drug
  • Food Toxin
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Selective Serotonin Reuptake Inhibitor
  • Serotonin Uptake Inhibitor
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-SertralineChEBI
(1S,4S)-SertralineChEBI
(1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamineChEBI
cis-(+)-SertralineChEBI
CP 51974ChEBI
SertralinaChEBI
SertralinumChEBI
Sertraline hydrochlorideHMDB
ZoloftHMDB
BesitranHMDB
Gen sertralineHMDB
Novo sertralineHMDB
Parke davis brand OF sertraline hydrochlorideHMDB
Ratiopharm brand OF sertraline hydrochlorideHMDB
Rhoxal sertralineHMDB
Sertraline hydrochloride (1S-cis)-isomerHMDB
AltrulineHMDB
LustralHMDB
Novo-sertralineHMDB
Rhoxalpharma brand OF sertraline hydrochlorideHMDB
Roerig brand OF sertraline hydrochlorideHMDB
SealdinHMDB
Ratio sertralineHMDB
Ratio-sertralineHMDB
Apo sertralineHMDB
Apo-sertralineHMDB
AremisHMDB
Boehringer ingelheim brand OF sertraline hydrochlorideHMDB
GlademHMDB
Pfizer brand OF sertraline hydrochlorideHMDB
Apotex brand OF sertraline hydrochlorideHMDB
Esteve brand OF sertraline hydrochlorideHMDB
Gen-sertralineHMDB
Genpharm brand OF sertraline hydrochlorideHMDB
Hydrochloride, sertralineHMDB
Lacer brand OF sertraline hydrochlorideHMDB
Novopharm brand OF sertraline hydrochlorideHMDB
Rhoxal-sertralineHMDB
Chemical FormulaC17H17Cl2N
Average Molecular Mass306.230 g/mol
Monoisotopic Mass305.074 g/mol
CAS Registry Number79617-96-2
IUPAC Name(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
Traditional Namesertraline
SMILESCN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12
InChI IdentifierInChI=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
InChI KeyVGKDLMBJGBXTGI-SJCJKPOMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tametralines. Tametralines are compounds containing a tametraline moiety, which consists of a tetrahydronaphthalene linked to a phenyl group to form N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine skeleton.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassTametralines
Direct ParentTametralines
Alternative Parents
Substituents
  • Tametraline
  • 1,2-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Secondary aliphatic amine
  • Secondary amine
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organochloride
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Liver
  • Platelet
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point243-245°C
Boiling PointNot Available
Solubility3.5mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.00014 g/LALOGPS
logP5.06ALOGPS
logP5.15ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.74 m³·mol⁻¹ChemAxon
Polarizability32.44 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-0490000000-724d07a27d5e8d538495Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0091000000-10f81c7fd0a8c096039dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-0980000000-58873180fd0c95a215b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0900000000-35c397f9293e114f3234Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-569e7b0694b3ef81cf90Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0970000000-2de49c544ebd922028dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0970000000-7753c869949091f5c066Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0970000000-a995c3f140efa6578777Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bt9-2900000000-dee4675a5062129266c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a6r-0950000000-2a9cba59b69c41b10a59Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a6r-0950000000-c83a31b55267aefe212aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-dd599a43cebe678e826dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-0900000000-f3cbee6abbbc3ca370b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-c5202d63a9c4b21b0775Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0910000000-565998e1b2eefa1c2ccbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-fef875b785017dd6bb4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0bt9-0900000000-1c524b8999874349f051Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-bf056f6f75a4ccc5d4c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-056r-0980000000-58873180fd0c95a215b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0091000000-10f81c7fd0a8c096039dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0139000000-4f4b68d5ff5484e81ce9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1779000000-742a47a4d5d21cc8acb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-1960000000-f03bdc5054705000574cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-d658426c80474367477aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-68fb5194b39f7a3d992bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kwo-4390000000-925d4346a5a2a057e466Spectrum
MSMass Spectrum (Electron Ionization)splash10-00b9-2890000000-d53a90b04ec8457ad2f1Spectrum
Toxicity Profile
Route of ExposureThe 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.
Mechanism of ToxicityThe 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.
MetabolismExtensively metabolized in the liver. Sertraline metabolism involves N-demethylation, N-hydroxylation, oxidative deamination, and glucuronidation of sertraline carbamic acid. Sertraline undergoes N-demethylation primarily catalyzed by cytochrome P450 (CYP) 2B6, with CYP2C19, CYP3A4 and CYP2D6 contributing to a lesser extent. Deamination occurs via CYP3A4 and CYP2C19. In vitro studies have shown that monoamine oxidase A and B may also catalyze sertraline deamination. Sertraline N-carbamoyl glucuronidation has also been observed in human liver microsomes. Route of Elimination: Sertraline is extensively metabolized and excretion of unchanged drug in urine is a minor route of elimination. Half Life: The elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of major depressive disorder, posttraumatic stress disorder, obsessive-compulsive disorder, panic disorder with or without agoraphobia, premenstrual dysphoric disorder, social phobia, premature ejaculation, and vascular headaches.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of toxicity include alopecia, decreased libido, diarrhea, ejaculation disorder, fatigue, insomnia, somnolence and serotonin syndrome.
TreatmentTreatment should consist of those general measures employed in the management of overdosage with any antidepressant. Ensure an adequate airway, oxygenation and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large-bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion, or in symptomatic patients. Activated charcoal should be administered. Due to large volume of distribution of this drug, forced diuresis, dialysis, hemoperfusion and exchange transfusion are unlikely to be of benefit. No specific antidotes for sertraline are known. (19)
Concentrations
Not Available
DrugBank IDDB01104
HMDB IDHMDB0005010
FooDB IDFDB023583
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2417
PDB IDSRE
Wikipedia LinkSertraline
Chemspider ID61881
ChEBI ID9123
PubChem Compound ID68617
Kegg Compound IDC07246
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

George J. Quallich, Michael T. Williams, “Process for preparing sertraline intermediates.” U.S. Patent US4839104, issued February, 1977.

MSDSNot Available
General References
1. Corey, E. J.; Gant, Thomas G. A catalytic enantioselective synthetic route to the important antidepressant sertraline. Tetrahedron Letters (1994), 35(30), 5373-6.
2. Agnel M, Esnaud H, Langer SZ, Graham D: Pharmacological characterization of the cloned human 5-hydroxytryptamine transporter. Biochem Pharmacol. 1996 May 3;51(9):1145-51.
3. Serebruany VL, Suckow RF, Cooper TB, O'Connor CM, Malinin AI, Krishnan KR, van Zyl LT, Lekht V, Glassman AH: Relationship between release of platelet/endothelial biomarkers and plasma levels of sertraline and N-desmethylsertraline in acute coronary syndrome patients receiving SSRI treatment for depression. Am J Psychiatry. 2005 Jun;162(6):1165-70.
4. Parsey RV, Kent JM, Oquendo MA, Richards MC, Pratap M, Cooper TB, Arango V, Mann JJ: Acute occupancy of brain serotonin transporter by sertraline as measured by [11C]DASB and positron emission tomography. Biol Psychiatry. 2006 May 1;59(9):821-8. Epub 2005 Oct 6.
5. Markovitz JH, Shuster JL, Chitwood WS, May RS, Tolbert LC: Platelet activation in depression and effects of sertraline treatment: An open-label study. Am J Psychiatry. 2000 Jun;157(6):1006-8.
6. Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. Epub 2004 Nov 16.
7. Epperson CN, Jatlow PI, Czarkowski K, Anderson GM: Maternal fluoxetine treatment in the postpartum period: effects on platelet serotonin and plasma drug levels in breastfeeding mother-infant pairs. Pediatrics. 2003 Nov;112(5):e425.
8. Serebruany VL, Gurbel PA, O'Connor CM: Platelet inhibition by sertraline and N-desmethylsertraline: a possible missing link between depression, coronary events, and mortality benefits of selective serotonin reuptake inhibitors. Pharmacol Res. 2001 May;43(5):453-62.
9. Kobayashi K, Yamamoto T, Chiba K, Tani M, Ishizaki T, Kuroiwa Y: The effects of selective serotonin reuptake inhibitors and their metabolites on S-mephenytoin 4'-hydroxylase activity in human liver microsomes. Br J Clin Pharmacol. 1995 Nov;40(5):481-5.
10. Phillips OM, Wood KM, Williams DC: Kinetics of the interaction of sertraline with the human platelet plasma membrane 5-hydroxytryptamine carrier. Eur J Pharmacol. 1988 Feb 9;146(2-3):299-306.
11. Pivac N, Muck-Seler D, Sagud M, Jakovljevic M, Mustapic M, Mihaljevic-Peles A: Long-term sertraline treatment and peripheral biochemical markers in female depressed patients. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Aug;27(5):759-65.
12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19502000
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21823671