SRE

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

Created: 2009-04-03
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count37
Chiral Atom Count2
Bond Count39
Aromatic Bond Count12
2D diagram of SRE

Chemical Component Summary

Name(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
SynonymsSertraline
Systematic Name (OpenEye OEToolkits)(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
FormulaC17 H17 Cl2 N
Molecular Weight306.23
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04Clc1ccc(cc1Cl)C3c2c(cccc2)C(NC)CC3
SMILESCACTVS3.341CN[CH]1CC[CH](c2ccc(Cl)c(Cl)c2)c3ccccc13
SMILESOpenEye OEToolkits1.5.0CNC1CCC(c2c1cccc2)c3ccc(c(c3)Cl)Cl
Canonical SMILESCACTVS3.341 CN[C@H]1CC[C@@H](c2ccc(Cl)c(Cl)c2)c3ccccc13
Canonical SMILESOpenEye OEToolkits1.5.0 CN[C@H]1CC[C@H](c2c1cccc2)c3ccc(c(c3)Cl)Cl
InChIInChI1.03 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
InChIKeyInChI1.03 VGKDLMBJGBXTGI-SJCJKPOMSA-N

Drug Info: DrugBank

DrugBank IDDB01104 
NameSertraline
Groups approved
DescriptionSertraline is a popular antidepressant medication commonly known as a selective serotonin reuptake inhibitor (SSRI), and is similar to drugs such as [Citalopram] and [Fluoxetine]. Despite marked structural differences between compounds in this drug class, SSRIs exert similar pharmacological effects. Several weeks of therapy with sertraline may be required before beneficial effects are noticed. Sertraline displays enhanced safety or tolerability than other classes of antidepressants, which frequently cause high levels of drowsiness, dizziness, blurred vision, and other undesirable effects.[A1846,A187075,T28]
Synonyms
  • Sertralinum
  • (1S-cis)-1,2,3,4-tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine
  • cis-(+)-sertraline
  • (+)-Sertraline
  • Sertraline
Brand Names
  • Teva-sertraline
  • Gd-sertraline
  • PHL-sertraline
  • Zoloft
  • Sertraline Hydrochloride
IndicationSertraline is indicated for the management of major depressive disorder (MDD), post-traumatic stress disorder (PTSD), obsessive-compulsive disorder (OCD), panic disorder (PD), premenstrual dysphoric disorder (PMDD), and social anxiety disorder (SAD).[L9016] Common off-label uses for sertraline include the prevention of post stroke depression[A187078], generalized anxiety disorder (GAD), fibromyalgia, premature ejaculation, migraine prophylaxis, diabetic neuropathy, and neurocardiogenic syncope.[L5227]
Categories
  • Agents that reduce seizure threshold
  • Amines
  • Antidepressive Agents
  • Antidepressive Agents Indicated for Depression
  • Central Nervous System Agents
ATC-CodeN06AB06
CAS number79617-96-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Sodium-dependent serotonin transporterMETTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...unknowninhibitor,binder,downregulator
Sodium-dependent dopamine transporterMSKSKCSVGLMSSVVAPAKEPNAVGPKEVELILVKEQNGVQLTSSTLTNP...unknowninhibitor,binder
Sigma receptorMAAEDVVATGADPSDLESGGLLHEIFTSPLNLLLLGLCIFLLYKIVRGDQ...unknowninhibitor,binder
Sodium-dependent noradrenaline transporterMLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...unknowninhibitor,downregulator
Equilibrative nucleoside transporter 4MGSVGSQRLEEPSVAGTPDPGVVMSFTFDSHQLEEAAEAAQGQGLRARGV...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL809
PubChem 68617
ChEMBL CHEMBL809
ChEBI CHEBI:9123
CCDC/CSD BATGIP, CAVVUQ01, IPIPIG, CAVVUQ, QAVWER, BATGOV, VAHHEU, LETBUL, LETBOF