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128196-01-0

Basic Information
CAS No.: 128196-01-0
Name: Escitalopram
Article Data: 41
Molecular Structure:
Molecular Structure of 128196-01-0 (Escitalopram)
Formula: C20H21FN2O
Molecular Weight: 324.398
Synonyms: 5-Isobenzofurancarbonitrile,1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (S)-;(+)-(S)-1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile;(+)-Citalopram;(S)-Citalopram;S-(+)-Citalopram;Seroplex;5-Isobenzofurancarbonitrile,1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (1S)-;
Density: 1.18 g/cm3
Boiling Point: 428.3 °C at 760 mmHg
Flash Point: 212.8 °C
Appearance: white or white crystalline powder
PSA: 110.86000
LogP: 2.96858
Downstream Products
219861-08-2
144025-14-9
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Chemistry


IUPAC name: (1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
Molecular Formula: C20H21FN2O
Molecular Weight: 324.392 g/mol
Classification Code: Antidepressive Agents; Antidepressive agents, second-generation; Central Nervous System Agents; Neurotransmitter Agents; Neurotransmitter Uptake Inhibitors; Psychotropic Drugs; Serotonin Agents; Serotonin uptake inhibitors
Index of Refraction: 1.591 
Molar Refractivity: 92.13 cm3 
Molar Volume: 272.6 cm3
Surface Tension: 49.8 dyne/cm 
Density: 1.18 g/cm3 
Flash Point: 212.8 °C 
Enthalpy of Vaporization: 68.35 kJ/mol 
Boiling Point: 428.3 °C at 760 mmHg 
Vapour Pressure of Escitalopram (CAS NO.128196-01-0): 1.53E-07 mmHg at 25 °C

History

 Escitalopram (CAS No.:128196-01-0) 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.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 "evergreening"(also called "lifecycle management")– 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.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.In 2006 Forest Laboratories was granted an 828 day (2 years and 3 months) extension on its patent for escitalopram.This pushed the patent expiry from December 7, 2009 to March 14, 2012.

Uses

 Despite the similarity of escitalopram and citalopram, preclinical as well as various clinical studies (including double-blinded studies) have shown differentiated effects of citalopram and escitalopram, as well as a clinical superiority compared with a variety of other SSRIs, such as paroxetine, especially in severely depressed patients. A head-to-head comparison of escitalopram with duloxetine found escitalopram to be both more tolerable and more effective. Compared with venlafaxine and sertraline, Escitalopram was shown to have similar efficacy.

Specification

 Escitalopram (CAS NO.128196-01-0), its Synonyms are (+)-(S)-1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile ; (S)-Citalopram ; S(+)-Citalopram ; Seroplex . It 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.