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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-16 12:40:06 UTC
Update Date2020-11-09 23:17:37 UTC
HMDB IDHMDB0005010
Secondary Accession Numbers
  • HMDB05010
Metabolite Identification
Common NameSertraline
DescriptionSertraline is a selective serotonin uptake inhibitor that is used in the treatment of depression. Sertraline hydrochloride (also labeled under numerous brand names: Zoloft, Sertralin, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is an orally administered antidepressant of the selective serotonin reuptake inhibitor (SSRI) type. It was first approved by the Food and Drug Administration (FDA) in 1991. Sertraline is an odorless, white, sparingly soluble crystalline solid. The minimum effective dose is usually 50 mg per day (it can be still effective at 25 mg or 37.5 mg), but lower doses may be used in the initial weeks of treatment to acclimate the patient's body, especially the liver, to the drug and to minimize the severity of any side effects. Patients who do not experience relief of symptoms at 50 mg a day may have their dose increased, up to 200 mg a day. Sertraline (HCl) is used medically mainly to treat the symptoms of depression and anxiety. It is also prescribed for the treatment of obsessive-compulsive disorder (OCD), post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD), panic disorder (PD) and social phobia/social anxiety disorder. A study has shown that sertraline is an effective treatment for impulsive aggressive behavior in personality disordered patients.
Structure
Data?1582752339
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 Weight306.23
Monoisotopic Molecular Weight305.073804963
IUPAC Name(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
Traditional Namesertraline
CAS Registry Number79617-96-2
SMILES
CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12
InChI Identifier
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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-0490000000-724d07a27d5e8d538495Spectrum
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
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
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Brain
  • Liver
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.15 (0.00032-0.32) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01104
Phenol Explorer Compound IDNot Available
FooDB IDFDB023583
KNApSAcK IDNot Available
Chemspider ID61881
KEGG Compound IDC07246
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSertraline
METLIN ID2417
PubChem Compound68617
PDB IDSRE
ChEBI ID9123
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceCorey, E. J.; Gant, Thomas G. A catalytic enantioselective synthetic route to the important antidepressant sertraline. Tetrahedron Letters (1994), 35(30), 5373-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:8645336 ]
  2. 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. [PubMed:15932816 ]
  3. 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. [PubMed:16213473 ]
  4. 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. [PubMed:10831484 ]
  5. 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. [PubMed:15547048 ]
  6. 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. [PubMed:14595087 ]
  7. 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. [PubMed:11394937 ]
  8. 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. [PubMed:8703653 ]
  9. 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. [PubMed:3371401 ]
  10. 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. [PubMed:12921906 ]
  11. 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. [PubMed:32033212 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165