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Human Metabolome Database: Showing metabocard for Sertraline (HMDB0005010)

Record InformationVersion5.0StatusDetected and QuantifiedCreation Date2006-10-16 12:40:06 UTCUpdate Date2022-03-07 02:49:25 UTCHMDB IDHMDB0005010Secondary Accession Numbers

HMDB05010

Metabolite IdentificationCommon NameSertralineDescriptionSertraline 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

CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12

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

Synonyms

Value	Source
(+)-Sertraline	ChEBI
(1S,4S)-Sertraline	ChEBI
(1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine	ChEBI
cis-(+)-Sertraline	ChEBI
CP 51974	ChEBI
Sertralina	ChEBI
Sertralinum	ChEBI
Sertraline hydrochloride	HMDB
Zoloft	HMDB
Besitran	HMDB
Gen sertraline	HMDB
Novo sertraline	HMDB
Parke davis brand OF sertraline hydrochloride	HMDB
Ratiopharm brand OF sertraline hydrochloride	HMDB
Rhoxal sertraline	HMDB
Sertraline hydrochloride (1S-cis)-isomer	HMDB
Altruline	HMDB
Lustral	HMDB
Novo-sertraline	HMDB
Rhoxalpharma brand OF sertraline hydrochloride	HMDB
Roerig brand OF sertraline hydrochloride	HMDB
Sealdin	HMDB
Ratio sertraline	HMDB
Ratio-sertraline	HMDB
Apo sertraline	HMDB
Apo-sertraline	HMDB
Aremis	HMDB
Boehringer ingelheim brand OF sertraline hydrochloride	HMDB
Gladem	HMDB
Pfizer brand OF sertraline hydrochloride	HMDB
Apotex brand OF sertraline hydrochloride	HMDB
Esteve brand OF sertraline hydrochloride	HMDB
Gen-sertraline	HMDB
Genpharm brand OF sertraline hydrochloride	HMDB
Hydrochloride, sertraline	HMDB
Lacer brand OF sertraline hydrochloride	HMDB
Novopharm brand OF sertraline hydrochloride	HMDB
Rhoxal-sertraline	HMDB

Chemical FormulaC₁₇H₁₇Cl₂NAverage Molecular Weight306.23Monoisotopic Molecular Weight305.073804963IUPAC Name(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amineTraditional NamesertralineCAS Registry Number79617-96-2SMILES

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-NChemical TaxonomyDescription 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 compoundsExternal Descriptors

secondary amino compound (CHEBI:9123 )
dichlorobenzene (CHEBI:9123 )
tetralins (CHEBI:9123 )

OntologyPhysiological effect

Health effect

Disposition

Biological location

Blood (PMID: 16862624)

Membrane (HMDB: HMDB0005010)
Cell membrane (HMDB: HMDB0005010)

Platelet (HMDB: HMDB0005010)

Urine (PMID: 32966057)

Route of exposure

Ingestion (HMDB: HMDB0005010)

Source

Exogenous (HMDB: HMDB0005010)

ProcessNot AvailableRole

Industrial application

Pharmaceutical (HMDB: HMDB0005010)

Antidepressant (HMDB: HMDB0005010)
Antidepressant (HMDB: HMDB0005010)

Biological role

Serotonin uptake inhibitor (HMDB: HMDB0005010)
Serotonin uptake inhibitor (HMDB: HMDB0005010)

Physical PropertiesStateSolidExperimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic PropertiesNot AvailablePredicted Molecular Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	5.06	ALOGPS
logP	5.15	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	9.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.74 m³·mol⁻¹	ChemAxon
Polarizability	32.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	202.253	30932474
DeepCCS	[M+Na]+	177.48	30932474
AllCCS	[M+H]+	169.6	32859911
AllCCS	[M+H-H2O]+	166.1	32859911
AllCCS	[M+NH4]+	172.8	32859911
AllCCS	[M+Na]+	173.7	32859911
AllCCS	[M-H]-	171.0	32859911
AllCCS	[M+Na-2H]-	170.6	32859911
AllCCS	[M+HCOO]-	170.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sertraline	CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12	3493.1	Standard polar	33892256
Sertraline	CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12	2406.8	Standard non polar	33892256
Sertraline	CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12	2405.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sertraline,1TMS,isomer #1	CN([C@H]1CC[C@@H](C2=CC=C(Cl)C(Cl)=C2)C2=CC=CC=C21)[Si](C)(C)C	2486.2	Semi standard non polar	33892256
Sertraline,1TMS,isomer #1	CN([C@H]1CC[C@@H](C2=CC=C(Cl)C(Cl)=C2)C2=CC=CC=C21)[Si](C)(C)C	2706.2	Standard non polar	33892256
Sertraline,1TMS,isomer #1	CN([C@H]1CC[C@@H](C2=CC=C(Cl)C(Cl)=C2)C2=CC=CC=C21)[Si](C)(C)C	2942.5	Standard polar	33892256
Sertraline,1TBDMS,isomer #1	CN([C@H]1CC[C@@H](C2=CC=C(Cl)C(Cl)=C2)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2676.2	Semi standard non polar	33892256
Sertraline,1TBDMS,isomer #1	CN([C@H]1CC[C@@H](C2=CC=C(Cl)C(Cl)=C2)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	2993.0	Standard non polar	33892256
Sertraline,1TBDMS,isomer #1	CN([C@H]1CC[C@@H](C2=CC=C(Cl)C(Cl)=C2)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C	3063.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sertraline GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-0490000000-724d07a27d5e8d538495	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sertraline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00b9-2890000000-d53a90b04ec8457ad2f1	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline LC-ESI-QTOF , positive-QTOF	splash10-004i-0091000000-10f81c7fd0a8c096039d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline LC-ESI-QTOF , positive-QTOF	splash10-056r-0980000000-58873180fd0c95a215b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline LC-ESI-QTOF , positive-QTOF	splash10-0bt9-0900000000-35c397f9293e114f3234	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-569e7b0694b3ef81cf90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline , positive-QTOF	splash10-056r-0970000000-2de49c544ebd922028dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline , positive-QTOF	splash10-056r-0970000000-7753c869949091f5c066	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline , positive-QTOF	splash10-056r-0970000000-a995c3f140efa6578777	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline , positive-QTOF	splash10-0bt9-2900000000-dee4675a5062129266c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline LC-ESI-QFT , positive-QTOF	splash10-0a6r-0950000000-2a9cba59b69c41b10a59	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 35V, Positive-QTOF	splash10-0a6r-0950000000-c83a31b55267aefe212a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 40V, Positive-QTOF	splash10-0a4i-0900000000-dd599a43cebe678e826d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 50V, Positive-QTOF	splash10-0a4i-0900000000-f3cbee6abbbc3ca370b4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 10V, Positive-QTOF	splash10-004i-0290000000-c5202d63a9c4b21b0775	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 20V, Positive-QTOF	splash10-0a4i-0910000000-565998e1b2eefa1c2ccb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 40V, Positive-QTOF	splash10-0a4i-0900000000-fef875b785017dd6bb4f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 30V, Positive-QTOF	splash10-0bt9-0900000000-1c524b8999874349f051	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 40V, Positive-QTOF	splash10-0a4i-0900000000-bf056f6f75a4ccc5d4c9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 20V, Positive-QTOF	splash10-056r-0980000000-58873180fd0c95a215b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sertraline 10V, Positive-QTOF	splash10-004i-0091000000-10f81c7fd0a8c096039d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertraline 10V, Positive-QTOF	splash10-0a4i-0139000000-4f4b68d5ff5484e81ce9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertraline 20V, Positive-QTOF	splash10-0a4i-1779000000-742a47a4d5d21cc8acb1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertraline 40V, Positive-QTOF	splash10-03xr-1960000000-f03bdc5054705000574c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertraline 10V, Negative-QTOF	splash10-0udi-0009000000-d658426c80474367477a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertraline 20V, Negative-QTOF	splash10-0udi-0029000000-68fb5194b39f7a3d992b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertraline 40V, Negative-QTOF	splash10-0kwo-4390000000-925d4346a5a2a057e466	2016-08-03	Wishart Lab	View Spectrum

Biological PropertiesCellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Brain
Liver
Placenta
Platelet

PathwaysNormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.15 (0.00032-0.32) uM	Adult (>18 years old)	Both	Normal	16862624	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal ConcentrationsNot AvailablePredicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and DiseasesDisease ReferencesNoneAssociated OMIM IDsNoneExternal LinksDrugBank IDDB01104 Phenol Explorer Compound IDNot AvailableFooDB IDFDB023583 KNApSAcK IDNot AvailableChemspider ID61881 KEGG Compound IDC07246 BioCyc IDNot AvailableBiGG IDNot AvailableWikipedia LinkSertraline METLIN ID2417 PubChem Compound68617 PDB IDSRE ChEBI ID9123 Food Biomarker OntologyNot AvailableVMH IDNot AvailableMarkerDB IDNot AvailableGood Scents IDNot AvailableReferencesSynthesis 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 AvailableGeneral References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]