Lexapro [Lexis(vocabulary) + Pro]
Escitalopram
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| Systematic (IUPAC) name | |
| (S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile | |
| Identifiers | |
| CAS number | 128196-01-0 |
| ATC code | N06AB10 |
| PubChem | CID 146570 |
| DrugBank | APRD00683 |
| ChemSpider | 129277 |
| UNII | 4O4S742ANY |
| Chemical data | |
| Formula | C20H21FN2O |
| Mol. mass | 324.392 g/mol (414.43 as oxalate) |
| SMILES | eMolecules & PubChem |
| Pharmacokinetic data | |
| Bioavailability | 80% |
| Protein binding | ~56% |
| Metabolism | Liver, specifically the enzymes CYP3A4 and CYP2C19 |
| Half-life | 27–32 hours |
| Therapeutic considerations | |
| Pregnancy cat. | C |
| Legal status | Rx Only (U.S) POM (U.K) |
| Routes | Oral |
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Escitalopram (trade names Lexapro, Cipralex, Seroplex, Lexamil) 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 in adults with major depressive disorder, generalized anxiety disorder, social anxiety disorder, or panic disorder. Escitalopram is the S-stereoisomer (enantiomer) of the earlier Lundbeck drug citalopram, hence the name escitalopram. Escitalopram is noted for its high selectivity of serotonin reuptake inhibition and has side effects typical for the SSRI class.
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[edit] History
Escitalopram was developed in a close cooperation between Lundbeck and Forest Laboratories. Its development was initiated in the summer of 1997, and the resulting new drug application was submitted to the U.S. FDA in March 2001. The short time (3.5 years) it took to develop escitalopram can be attributed to the previous extensive experience of Lundbeck and Forest with citalopram, which has similar pharmacology.[1]evergreening"[2] (also called "lifecycle management"[3])– the long-term strategy pharmaceutical companies use in order to extend the lifetime of a drug, in this case of the citalopram franchise. Escitalopram is an enantiopure compound of the racemic mixture citalopram, used for the same indication, and for that reason it required less investment and less time to develop. Two years after escitalopram's launch, when the patent on citalopram expired, the escitalopram sales successfully made up for the loss. On May 23, 2006, the FDA approved a generic version of escitalopram by Teva.[4] On July 14 of that year, however, the U.S. District Court of Delaware decided in favor of Lundbeck regarding the patent infringement dispute and ruled the patent on escitalopram valid.[5] The FDA issued the approval of escitalopram for major depression in August 2002 and for generalized anxiety disorder in December 2003. Escitalopram can be considered an example of "
In 2006 Forest Laboratories was granted an 828 day (2 years and 3 months) extension on its US patent for escitalopram.[6] This pushed the patent expiry from December 7, 2009 to March 14, 2012.
