29E

(3S)-N-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine

Created: 2013-09-11
Last modified:  2020-04-05

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Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count1
Bond Count42
Aromatic Bond Count16
2D diagram of 29E

Chemical Component Summary

Name(3S)-N-methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine
SynonymsDuloxetine
Systematic Name (OpenEye OEToolkits)(3S)-N-methyl-3-naphthalen-1-yloxy-3-thiophen-2-yl-propan-1-amine
FormulaC18 H19 N O S
Molecular Weight297.415
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O(c1cccc2c1cccc2)C(c3sccc3)CCNC
SMILESCACTVS3.385CNCC[CH](Oc1cccc2ccccc12)c3sccc3
SMILESOpenEye OEToolkits1.7.6CNCCC(c1cccs1)Oc2cccc3c2cccc3
Canonical SMILESCACTVS3.385 CNCC[C@H](Oc1cccc2ccccc12)c3sccc3
Canonical SMILESOpenEye OEToolkits1.7.6 CNCC[C@@H](c1cccs1)Oc2cccc3c2cccc3
InChIInChI1.03 InChI=1S/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m0/s1
InChIKeyInChI1.03 ZEUITGRIYCTCEM-KRWDZBQOSA-N

Drug Info: DrugBank

DrugBank IDDB00476 
NameDuloxetine
Groups approved
DescriptionDuloxetine is a dual serotonin and norepinephrine reuptake inhibitor.[label] It was originally discovered in 1993 and developed by Eli Lilly and Company as LY248686.[A178741] Duloxetine first received approval from the FDA in August, 2004 as Cymbalta for the treatment of Major Depressive Disorder.[L6454] It has since received approval for a variety of indications including the treatment of neuropathic pain, Generalized Anxiety disorder, osteoarthritis, and stress incontinence. Duloxetine continues to be investigated for the treatment of pain in cancer, surgery, and more.
Synonyms
  • (3S)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine
  • Duloxetine
  • (S)-duloxetine
  • Duloxetine hydrochloride
  • Duloxetina
Brand Names
  • Dom-duloxetine
  • Taro-duloxetine
  • Mar-duloxetine
  • Duloxicaine
  • Irenka
Indication**Indicated** for: 1) Management of Major Depressive Disorder.[label] 2) Management of Generalized Anxiety Disorder.[label] 3) Management of diabetic peripheral neuropathy.[label] 4) Management of fibromyalgia.[label] 5) Management of chronic musculoskeletal pain.[label] 6) Management of osteoarthritis of the knee in adults.[L6364] 7) Management of chronic lower back pain in adults.[L6364] 8) Management of stress urinary incontinence in adult women.[L6367] **Off-label** uses include: 1) Management of chemotherapy-induced peripheral neuropathy.[A178603] 2) Management of stress urinary incontinence in adult men after prostatectomy until recovery is complete.[L6370]
Categories
  • Agents producing tachycardia
  • Analgesics
  • Antidepressive Agents
  • Antidepressive Agents Indicated for Depression
  • Central Nervous System Agents
ATC-CodeN06AX21
CAS number116539-59-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Sodium-dependent serotonin transporterMETTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...unknowninhibitor
Sodium-dependent noradrenaline transporterMLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...unknowninhibitor
Sodium-dependent dopamine transporterMSKSKCSVGLMSSVVAPAKEPNAVGPKEVELILVKEQNGVQLTSSTLTNP...unknowninhibitor
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknownsubstrate,inhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
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 CHEMBL1175
PubChem 60835
ChEMBL CHEMBL1175
ChEBI CHEBI:36795