Escitalopram

Base Information

• Chemical Name: Escitalopram
• CAS No.: 128196-01-0
• Molecular Formula: C20H21FN2O
• Molecular Weight: 324.398
• Hs Code.: 2932999099
• European Community (EC) Number: 812-870-6
• UNII: 4O4S742ANY
• DSSTox Substance ID: DTXSID8048440
• Nikkaji Number: J819.065H
• Wikipedia: Escitalopram
• Wikidata: Q423757
• NCI Thesaurus Code: C61754
• RXCUI: 321988
• Pharos Ligand ID: G1JNG1T28D4V
• Metabolomics Workbench ID: 38711
• ChEMBL ID: CHEMBL1508
• Mol file: 128196-01-0.mol

Synonyms:Escitalopram;Escitalopram Oxalate;Lexapro

Chemical Property of Escitalopram

Chemical Property:

• Appearance/Colour: white or white crystalline powder
• Vapor Pressure: 8.04E-15mmHg at 25°C
• Boiling Point: 428.3 °C at 760 mmHg
• PKA: 9.57±0.28(Predicted)
• Flash Point: 212.8 °C
• PSA: 110.86000
• Density: 1.18 g/cm³
• LogP: 2.96858
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 324.16379146
• Heavy Atom Count: 24
• Complexity: 466

Purity/Quality:

98% up, ^*data from raw suppliers

Escitalopram ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
• Isomeric SMILES: CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
• Recent ClinicalTrials: Vortioxetine in the Elderly vs. Selective Serotonin Reuptake Inhibitors (SSRIs): a Pragmatic Assessment
• Recent EU Clinical Trials: Investigation of SSRI induced neuroplastic changes in musicians using functional magnetic resonance imaging
• Recent NIPH Clinical Trials: The effect of Escitalopram on REM sleep behavior disorder
• Uses: antidepressive;selective serotonin reuptake inhibitor (S)-Citalopram is an inhibitor of serotonin (5-HT) uptake. Antidepressant.
• Clinical Use: SSRI antidepressant:Depressive illnessPanic and social anxiety disorder
• Drug interactions: Potentially hazardous interactions with other drugsAnalgesics: increased risk of bleeding with aspirin and NSAIDs; risk of CNS toxicity increased with tramadol.Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone, disopyramide and dronedarone - avoid.Antibacterials: increased risk of ventricular arrhythmias with IV erythromycin, moxifloxacin, pentamidine and telithromycin.Anticoagulants: effect of coumarins possibly enhanced; possibly increased risk of bleeding with dabigatran.Antidepressants: avoid concomitant use with MAOI, increased risk of toxicity; increased risk of CNS toxicity with moclobemide - avoid concomitant use; avoid concomitant use with St John’s wort; possibly enhanced serotonergic effects with dapoxetine and duloxetine; can increase concentration of tricyclics; increased agitation and nausea with tryptophan; increased risk of CNS toxicity with rasagiline; possible increased risk of convulsions with vortioxetineAntiepileptics: convulsive threshold lowered.Antihistamines: increased risk of ventricular arrhythmias with mizolastine - avoid.Antimalarials: avoid concomitant use with artemether/lumefantrine and piperaquine with artenimol; possible increased risk of ventricular arrhythmias with chloroquine and quinine.Antipsychotics: possibly increased risk of ventricular arrhythmias with haloperidol, phenothiazines and pimozide - avoid.Antivirals: concentration possibly increased by ritonavir.Beta-blockers: increased risk of ventricular arrhythmias with sotalol - avoid.Dopaminergics: avoid with selegiline; increased risk of CNS toxicity with rasagiline.5HT1 agonist: increased risk of CNS toxicity with sumatriptan; possibly increased risk of serotonergic effects with naratriptan.Linezolid: use with care, possibly increased risk of side effects.Lithium: increased risk of CNS effectsMethylthioninium: risk of CNS toxicity - avoid if possible.

Technology Process of Escitalopram

There total 52 articles about Escitalopram which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(+)-(S)-citalopram hydrobromide → escitalopram (128196-01-0)

Guidance literature:

With ammonia; In diethyl ether; water; pH=9 - 9.5;

Reference yield: 99.9%

escitalopram oxalate (219861-08-2) → escitalopram (128196-01-0)

Guidance literature:

With ammonium hydroxide; In water; at 20 ℃; pH=7.7; Product distribution / selectivity;

Reference yield: 95.0%

(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile (488787-59-3,219861-18-4,481047-48-7) → escitalopram (128196-01-0)

Guidance literature:

(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile; With triethylamine; p-toluenesulfonyl chloride; In toluene; at 20 ℃; for 0.333333h;

With ammonia; In water; toluene; at 45 ℃; for 0.0333333h;

upstream raw materials:

(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile

(S)-(+)-3-(5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-5-bromo-1,3-dihydroisobenzofuran methanesulfonate salt

Downstream raw materials:

(S)-1-(3-chloropropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

(+)-Desmethylcitalopram

S-citalopram hydrochloride

escitalopram oxalate

Refernces

• 1、 Elati, Chandrashekar R.,Kolla, Naveenkumar,Vankawala, Pravinchandra J.,Gangula, Srinivas,Chalamala, Subrahmanyeswarara,Sundaram, Venkatraman,Bhattacharya, Apurba,Vurimidi, Himabindu,Mathad, Vijayavitthal T.. "Substrate modification approach to achieve efficient resolution: Didesmethylcitalopram: A key intermediate for escitalopram". . p. 289 - 292. Retrieved 2007.
• 2、 Mital, Alka,Kumar, Rakesh,Ramachandran, Uma. "An improved resolution process for the preparation of antidepressant drug: Escitalopram". . p. 423 - 426. Retrieved 2006.
• 3、 -. "NEW SALT AND SOLID STATE FORMS OF ESCITALOPRAM". Paragraph 061. . Retrieved 2019/05/02.