8PR

Paroxetine

Created: 2011-07-11
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count44
Chiral Atom Count2
Bond Count47
Aromatic Bond Count12
2D diagram of 8PR

Chemical Component Summary

NameParoxetine
Synonyms(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
Systematic Name (OpenEye OEToolkits)(3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine
FormulaC19 H20 F N O3
Molecular Weight329.365
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Fc1ccc(cc1)C2CCNCC2COc3ccc4OCOc4c3
SMILESCACTVS3.370Fc1ccc(cc1)[CH]2CCNC[CH]2COc3ccc4OCOc4c3
SMILESOpenEye OEToolkits1.7.2c1cc(ccc1C2CCNCC2COc3ccc4c(c3)OCO4)F
Canonical SMILESCACTVS3.370 Fc1ccc(cc1)[C@@H]2CCNC[C@H]2COc3ccc4OCOc4c3
Canonical SMILESOpenEye OEToolkits1.7.2 c1cc(ccc1[C@@H]2CCNC[C@H]2COc3ccc4c(c3)OCO4)F
InChIInChI1.03 InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1
InChIKeyInChI1.03 AHOUBRCZNHFOSL-YOEHRIQHSA-N

Drug Info: DrugBank

DrugBank IDDB00715 
NameParoxetine
Groups
  • approved
  • investigational
DescriptionParoxetine is a selective serotonin reuptake inhibitor (SSRI) drug commonly known as Paxil. It has a variety of uses, including the treatment of anxiety disorders, major depression, posttraumatic stress disorder, and symptoms of menopause, among others.[T653] It was approved by the FDA in the early 1990s and marketed by SmithKline Beecham.[L7712,L7715] A unique feature of this drug is that it is highly potent and selective in its inhibition of serotonin reuptake and has little effect on other neurotransmitters.[A31914] Because of its potent inhibition of serotonin reuptake, paroxetine is more likely to cause withdrawal effects upon cessation. Paroxetine is well tolerated in most patients with a similar adverse effect profile to other members of its drug class.[A31914] The controlled release formulation was designed to decrease the likelihood of nausea that is sometimes associated with paroxetine.[L7700,L7742]
Synonyms
  • Paroxetine
  • Paroxetine mesylate
  • Paroxetine hydrochloride
  • Paroxetina
  • Paroxetinum
Brand Names
  • Brisdelle
  • Paxil CR
  • Ntp-paroxetine
  • Paxilcr CR
  • Priva-paroxetine
IndicationParoxetine is indicated for the management of depression, obsessive-compulsive disorder, panic disorder, social anxiety disorder, generalized anxiety disorder, posttraumatic stress disorder.[L3358] One form of paroxetine, commercially known as Brisdelle, is used to manage mild to moderate vasomotor symptoms of menopause.[L7703] Off-label, paroxetine may be used for the treatment of premature ejaculation or irritable bowel syndrome (IBS).[A1093,A181754,A181904]
Categories
  • Agents producing tachycardia
  • Anticholinergic Agents
  • Antidepressive Agents
  • Antidepressive Agents Indicated for Depression
  • Antidepressive Agents, Second-Generation
ATC-CodeN06AB05
CAS number61869-08-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Sodium-dependent serotonin transporterMETTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...unknowninhibitor
Sodium-dependent noradrenaline transporterMLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...unknowninhibitor
5-hydroxytryptamine receptor 2AMDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...unknownagonist
Alpha-1 adrenergic receptorsMVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...unknownbinder
Alpha-2 adrenergic receptorsMGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...unknownbinder
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 CHEMBL490
PubChem 43815
ChEMBL CHEMBL490
ChEBI CHEBI:7936
CCDC/CSD EHOXEE, DIZSOX, ALIGUZ, DIZSUD, GODVAW01, GODVAW, DETGER, DIZSIR