Showing Compound Sertraline (FDB023583)

Record Information

Version

1.0

Creation date

2011-09-21 00:31:57 UTC

Update date

2015-07-21 06:57:46 UTC

Primary ID

FDB023583

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sertraline

Description

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. [HMDB]

CAS Number

79617-96-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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

Predicted 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

Chemical Formula

C17H17Cl2N

IUPAC name

(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

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 Key

VGKDLMBJGBXTGI-SJCJKPOMSA-N

Isomeric SMILES

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

Average Molecular Weight

306.23

Monoisotopic Molecular Weight

305.073804963

Classification

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

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

Ontology

Physiological effect

Health effect:

Health condition:

Gastrointestinal disorders:

Diarrhea

General disorders and administration site conditions:

Fatigue

Psychiatric disorders:

Insomnia

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Element:

Platelet

Organ and components:

Subcellular:

Biofluid and excreta:

Blood

Role

Biological role:

Serotonin uptake inhibitor

Industrial application:

Drug

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00b9-2890000000-d53a90b04ec8457ad2f1	2014-09-20	View Spectrum
Predicted GC-MS	Sertraline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-0490000000-724d07a27d5e8d538495	Spectrum
Predicted GC-MS	Sertraline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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