Escitalopram oxalate

Base Information

• Chemical Name: Escitalopram oxalate
• CAS No.: 219861-08-2
• Molecular Formula: C22H23FN2O5
• Molecular Weight: 414.433
• Hs Code.: 29322090
• European Community (EC) Number: 620-544-8
• NSC Number: 758934
• UNII: 5U85DBW7LO
• DSSTox Substance ID: DTXSID1046003
• Wikidata: Q27262882
• NCI Thesaurus Code: C47518
• RXCUI: 353108
• Pharos Ligand ID: G1JNG1T28D4V
• ChEMBL ID: CHEMBL1200322
• Mol file: 219861-08-2.mol

Synonyms:Escitalopram;Escitalopram Oxalate;Lexapro

Chemical Property of Escitalopram oxalate

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 152-153 °C
• Boiling Point: 428.3 °C at 760 mmHg
• Flash Point: 212.8 °C
• PSA: 110.86000
• LogP: 2.96858
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO: ≥15mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 414.15910000
• Heavy Atom Count: 30
• Complexity: 537

Purity/Quality:

99%, ^*data from raw suppliers

Escitalopram oxalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

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.C(=O)(C(=O)O)O
• Isomeric SMILES: CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.C(=O)(C(=O)O)O
• Recent ClinicalTrials: Efficacy of Hydroxyzine for Patients With Panic Disorder
• Recent EU Clinical Trials: Investigation of SSRI induced neuroplastic changes in musicians using functional magnetic resonance imaging
• Description: Escitalopram was launched as Cipralex? in Switzerland, Sweden and UK for the treatment of depression and panic disorder. It is the S-enantiomer version of the selective serotonin reuptake inhibitor (SSRI) citalopram approved in 1989. It can be obtained from 5cyanophthalide by successive reactions with 4-fluorophenyl magnesium bromide and 3-(dimethylamino)propyl magnesium chloride. The resulting racemic diol can be resolved by several routes such as crystallization with a chiral acid. Finally, a two step cyclisation procedure affords escitalopram. Escitalopram is twice as effective as the racemate and over 100 fold more potent than the R-enantiomer in inhibiting the 5HT reuptake in vivo in rat brain synaptosomes. Moreover, it exhibits higher selectivity for the human serotonin transporter relative to the noradrenaline or dopamine transporters than any other currently available SSRl’s. In the mouse forced swim test, the duration of immobility (which reflects antidepressant activity) for escitalopram was comparable to citalopram and greater than (R)-citalopram. Clinical trials in patients with panic disorders or depression have shown that escitalopram has a clinically relevant and significant effect. Additionally, it has a faster onset of antidepressant action than citalopram. Escitalopram has linear pharmacokinetics, with a long half-life (27-32 h). It is extensively metabolized in the liver via cytochromes P450 to S(+)-desmethyl and S(+)-didesmethyl citalopram. However, it has been shown to be a weak or negligible inhibitor of CYP450 drugmetabolizing enzymes in vitro. Escitalopram is well tolerated with nausea being the most common side effect.
• Uses: Escitalopram oxalate may be used as a pharmaceutical primary standard for the quantification of the analyte in pharmaceutical formulations using analytical techniques. An inhibitor of serotonin (5-HT) uptake. Antidepressant A labelled inhibitor of serotonin (5-HT) uptake. Antidepressant antineoplastic

Technology Process of Escitalopram oxalate

There total 19 articles about Escitalopram oxalate 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: 98.57%

oxalic acid (144-62-7,97993-78-7) + escitalopram (128196-01-0) → escitalopram oxalate (219861-08-2)

Guidance literature:

In acetone; at 25 - 30 ℃; Industry scale;

Reference yield: 85.0%

(1S)-4-[4-(dimethylamino)-1-(4'-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hemi-(+)-di-(p-toluoyl) tartaric acid salt (128173-53-5,912452-31-4) + oxalic acid (144-62-7,97993-78-7) → escitalopram oxalate (219861-08-2)

Guidance literature:

(1S)-4-[4-(dimethylamino)-1-(4'-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hemi-(+)-di-(p-toluoyl) tartaric acid salt; With sodium hydroxide; In diethyl ether; water; at 25 ℃; for 0.5h;

With triethylamine; In diethyl ether; water; toluene; at 5 ℃; for 0.5h;

oxalic acid; Further stages;

Reference yield: 82.0%

(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(4-nitrobenzoyloxymethyl)benzonitrile hydrochloride + oxalic acid (144-62-7,97993-78-7) → escitalopram oxalate (219861-08-2)

Guidance literature:

(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(4-nitrobenzoyloxymethyl)benzonitrile hydrochloride; With sodium hydrogencarbonate; In water; ethyl acetate;

With potassium carbonate; In dimethyl sulfoxide; at 90 - 100 ℃; for 2h;

oxalic acid;

upstream raw materials:

oxalic acid

escitalopram

formaldehyd

(S)-citalopram (L)-tartrate

Downstream raw materials:

escitalopram

Refernces

• 1、 -. "A New method for the production of citalopram and escitalopram using carbonates". Paragraph 0057-0061. . Retrieved 2020/06/02.
• 2、 -. "PROCESS FOR PRODUCING (1S)-4-[4-(DIMETHYLAMINO)-1-(4'-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-(HYDROXYMETHYL)-BENZONITRILE HEMI(+)-DI-(p-TOLUOYL) TARTARIC ACID SALT, AND PROCESS FOR PRODUCING (1S)-1-[3-(DIMETHYLAMINO)PROPYL]-1-(4-FLUOROPHENYL)-1,3-DIHYDRO-ISOBENZOFURAN-5-CARBO-NITRILE AND SALT THEREOF USING SAID TARTARIC ACID SALT". Paragraph 0063. . Retrieved 2018/07/28.