Escitalopram

Escitalopram

Clinical data
Pronunciation	pronunciation
Trade names	Cipralex, Lexapro and many others
AHFS/Drugs.com	Monograph
MedlinePlus	a603005
License data	US FDA: Lexapro
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	N06AB10 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	80%
Protein binding	~56%
Metabolism	Liver, specifically the enzymes CYP3A4 and CYP2C19
Biological half-life	27–32 hours
Identifiers
IUPAC name (1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
CAS Number	128196-01-0 Y
PubChem (CID)	146570
DrugBank	DB01175 N
ChemSpider	129277 Y
UNII	4O4S742ANY Y
ChEBI	CHEBI:36791 Y
ChEMBL	CHEMBL1508 Y
Chemical and physical data
Formula	C20H21FN2O
Molar mass	324.392 g/mol (414.43 as oxalate)
3D model (Jmol)	Interactive image
SMILES Fc1ccc(cc1)[C@@]3(OCc2cc(C#N)ccc23)CCCN(C)C
InChI InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1 Y Key:WSEQXVZVJXJVFP-FQEVSTJZSA-N Y
NY (what is this?)

Escitalopram, also known by the brand names Lexapro and Cipralex among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is approved by the U.S. Food and Drug Administration (FDA) for the treatment of adults and children over 12 years of age with major depressive disorder (MDD) or generalized anxiety disorder (GAD). Escitalopram is the (S)-stereoisomer (Left-enantiomer) of the earlier Lundbeck drug citalopram, hence the name escitalopram. Whether escitalopram exhibits superior therapeutic properties to citalopram or merely represents an example of "evergreening" is controversial.

The utility of antidepressant drugs in the treatment of mild-to-moderate depression is itself controversial. In those with very severe depression there is a large benefit.

Escitalopram has FDA approval for the treatment of major depressive disorder in adolescents and adults, and generalized anxiety disorder in adults. In European countries and Australia, it is approved for depression (MDD) and certain anxiety disorders: general anxiety disorder (GAD), social anxiety disorder (SAD), obsessive-compulsive disorder (OCD), and panic disorder with or without agoraphobia.

Escitalopram was approved by regulatory authorities for the treatment of major depressive disorder on the basis of four placebo controlled, double-blind trials, three of which demonstrated a statistical superiority over placebo. Nonetheless, considerable controversy exists regarding the superiority of escitalopram to its predecessor citalopram. The importance of this issue follows from the greater cost of escitalopram relative to the generic mixture of isomers citalopram prior to the expiration of the escitalopram patent in 2012, which led to charges of evergreening. Accordingly, this issue has been examined in at least 10 different systematic reviews and meta analyses. The most recent of these have concluded (with caveats in some cases) that escitalopram is modestly superior to citalopram in efficacy and/or tolerability.