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Paroxetine
Paroxetine
Synonyms None notable
Brand names Aropax, Extine, Paxil, Paxtine, Seroxat and others
IUPAC name

IUPAC name
(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
ChemSpider

39888

DrugBank

DB00715

PubChem

43815

PDB fields

N/A

Formula

CH

InChI
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
InChIKey
InChIKey
AHOUBRCZNHFOSL-YOEHRIQHSA-N
SMILES
SMILES
FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1
(Jmol 3D structure)
Mol. mass

Paroxetine is a selective serotonin reuptake inhibitor (SSR) that has numerous disadvantages when compared to the other SSRIs, for one it has a higher incidence of sexualanticholinergic and weight-related side effects and inhibits CYP2D6 very potently, hence being more prone than most other SSRIs to cause drug interactions.[1] It is also the sole SSRI that has been associated with an increased risk of congenital heart defects, if taken during pregnancy.[2][3] Its usual dosage range is 20-50 mg/day and is a phenylpiperidine.[4] It is approved by the Therapeutic Goods Administration (TGA) approved for the treatment of six psychiatric conditions, namely, major depression, obsessive-compulsive disorder, panic disorder, generalized anxiety disorder, post-traumatic stress disorder and social phobia),[4] and is Food and Drug Administration (FDA) approved for an additional two indications: premenstrual dysphoric disorder and menopausal vasomotor symptoms.[5]

It has the shortest half-life of all SSRIs at 17 hours and is metabolized predominantly by CYP2D6 and has no active metabolites.[6]


3D modelsEdit

Static structure
Paroxetine
Animated structure
400px Paroxetine


External linksEdit

Reference listEdit

  1. Brunton, L; Chabner, B; Knollman, B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (12th ed.). New York, USA: McGraw-Hill Professional. ISBN 978-0-07-162442-8. 
  2. "Is it safe to use SSRIs during pregnancy?". Health News and Evidence. Strawberry Hills, Australia: NPS MedicineWise. 8 March 2013. Retrieved 15 August 2014. 
  3. Williams, AS (October 2007). "Antidepressants in pregnancy and breastfeeding". Australian Prescriber (Strawberry Hills, Australia: NPS MedicineWise) 30 (5): 125–127. 
  4. 4.0 4.1 Rossi, S, ed. (July 2014). "Paroxetine". Australian Medicines Handbook. Adelaide, Australia: Australian Medicines Handbook Pty Ltd. 
  5. "Paxil, Paxil CR (paroxetine) dosing, indications, interactions, adverse effects, and more". Medscape Reference. United States of America: WebMD. Retrieved 10 October 2014. 
  6. Brunton, LL; Chabner, BA; Knollmann, BC, ed. (2010). Goodman & Gilman's Pharmacological Basis of Therapeutics. (12th ed.). New York, USA: McGraw-Hill Professional. ISBN 9780071624428. 

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