Escitalopram

Escitalopram
Clinical data
Pronunciation	/ˌɛsəˈtæləˌpræm/
Trade names	Cipralex, Lexapro, others
Other names	(S)-Citalopram; S-Citalopram; S-(+)-Citalopram; S(+)-Citalopram; (+)-Citalopram; LU-26054; MLD-55
AHFS/Drugs.com	Monograph
MedlinePlus	a603005
License data	US DailyMed: Escitalopram;
Pregnancy; category	AU: C;
Routes of; administration	By mouth
Drug class	Selective serotonin reuptake inhibitor (SSRI)
ATC code	N06AB10 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	~80%
Protein binding	~55–56% (low)
Metabolism	Liver (CYP2C19, CYP3A4, CYP2D6)
Metabolites	• Desmethylcitalopram; • Didesmethylcitalopram
Elimination half-life	~27–32 hours
Excretion	Urine (major; 8–10% unchanged), feces (minor)
Identifiers
	IUPAC name (S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile;
CAS Number	128196-01-0 ;
PubChem CID	146570;
DrugBank	DB01175 ;
ChemSpider	129277 ;
UNII	4O4S742ANY;
KEGG	D07913;
ChEBI	CHEBI:36791 ;
ChEMBL	ChEMBL1508 ;
CompTox Dashboard (EPA)	DTXSID8048440 ;
ECHA InfoCard	100.244.188
Chemical and physical data
Formula	C20H21FN2O
Molar mass	324.399 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Levorotatory enantiomer
	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 ; Key:WSEQXVZVJXJVFP-FQEVSTJZSA-N ;
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Escitalopram ( /ˌɛsəˈtæləˌpræm/ ^ⓘ eh-sə-TA-lə-pram), sold under the brand names Lexapro and Cipralex, among others, is an antidepressant medication of the selective serotonin reuptake inhibitor (SSRI) class. It is mainly used to treat major depressive disorder, generalized anxiety disorder, panic disorder, obsessive–compulsive disorder (OCD), and social anxiety disorder. Escitalopram is taken by mouth. For commercial use, it is formulated as an oxalate salt exclusively.

Common side effects include headache, nausea, sexual problems, mild sedation, and trouble sleeping. More serious side effects may include suicidal thoughts in people up to the age of 24 years. It is unclear if use during pregnancy or breastfeeding is safe. Escitalopram is the (S)-enantiomer of citalopram (which exists as a racemate), hence the name es-citalopram.

Escitalopram was approved for medical use in the United States in 2002. Escitalopram is rarely replaced by twice the dose of citalopram; escitalopram is safer and more effective. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the second most prescribed antidepressant and fifteenth most commonly prescribed medication in the United States, with more than 30 million prescriptions. In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.

Other first-line SSRIs that have similar results include sertraline, paroxetine and fluoxetine among others.