Paxil

Paroxetine

Clinical data
Trade names	Paxil, Pexeva, Seroxat, Brisdelle, Rexetin
AHFS/Drugs.com	Monograph
MedlinePlus	a698032
License data	US FDA: Paroxetine
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Oral
ATC code	N06AB05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Extensively absorbed from the GI tract, but extensive first-pass metabolism in the liver
Protein binding	93–95%
Metabolism	Extensive, hepatic (mostly CYP2D6-mediated)
Biological half-life	21 hours
Excretion	Renal (64%; 2% unchanged and 62% as metabolites), Faecal (36%; <1% unchanged)
Identifiers
IUPAC name (3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
CAS Number	61869-08-7 Y
PubChem CID	43815
IUPHAR/BPS	4790
DrugBank	DB00715 Y
ChemSpider	39888 Y
UNII	41VRH5220H
KEGG	D02362 Y
ChEBI	CHEBI:7936 N
ChEMBL	CHEMBL490 Y
ECHA InfoCard	100.112.096
Chemical and physical data
Formula	C19H20FNO3
Molar mass	329.3 g/mol
3D model (Jmol)	Interactive image
SMILES c1cc(ccc1[C@@H]2CCNC[C@H]2COc3ccc4c(c3)OCO4)F
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 Y Key:AHOUBRCZNHFOSL-YOEHRIQHSA-N Y
NY (what is this?)

Paroxetine, also known by the trade names Paxil and Seroxat among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive-compulsive disorder, social anxiety disorder, panic disorder, posttraumatic stress disorder, generalized anxiety disorder and premenstrual dysphoric disorder. It has also been used in the treatment of hot flashes and night sweats associated with menopause.

It has a similar tolerability profile to other SSRIs. The common side effects include drowsiness, dry mouth, loss of appetite, sweating, trouble sleeping and delayed ejaculation. It may also be associated with a slightly increased risk of birth defects. The rate of withdrawal symptoms in young people may be higher with paroxetine and venlafaxine than other SSRIs and SNRIs. Several studies have associated paroxetine with suicidal thinking and behavior in children and adolescents.

Marketing of the drug began in 1992 by the pharmaceutical company SmithKline Beecham, known since 2000 as GlaxoSmithKline. Generic formulations have been available since 2003 when the patent expired. The United States Department of Justice fined GlaxoSmithKline $3 billion in 2012, including a sum for withholding data on paroxetine, unlawfully promoting it for under-18s and preparing an article, following one of its clinical trials, study 329, that misleadingly reported the drug was effective in treating adolescent depression.