Introduction：Basic information about Escitalopram oxalate CAS 219861-08-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Escitalopram oxalate Basic information
| Product Name: | Escitalopram oxalate |
| Synonyms: | (S)-CITALOPRAM;1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran-carbonitrile oxalate;ESCITALOPRAM OXALATE;S-(+)-CITAPROLAM OXALATE;S-(+)-1-3-(dimethyl-amino)propyl-1-(p-fluorophenyl)-5-phthalancarbonitrileoxalate;ESCIFALOPRAMOXALATE;(S)-Citalopram-d6;1S)-1-[3-(Dimethylamino-d6)propyl]-1-(4-fluorophenyl)-1,3-dihydro -5-isobenzofurancarbonitrile |
| CAS: | 219861-08-2 |
| MF: | C22H23FN2O5 |
| MW: | 414.43 |
| EINECS: | 620-544-8 |
| Product Categories: | Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals;Heterocyclic Compounds;Antidepressant;Inhibitors;Other APIs;CHLORESIUM;Pharmaceutical intermdiate;Aromatics;Chiral Reagents;Heterocycles;Isotope Labelled Compounds;Isotope Labeled Compounds;Escitalopram |
| Mol File: | 219861-08-2.mol |
|
Escitalopram oxalate Chemical Properties
| Melting point | 152-153°C |
| alpha | D +12.31° (c = 1 in methanol) |
| storage temp. | 2-8°C |
| solubility | DMSO: ≥15mg/mL |
| form | powder |
| color | white to tan |
| Merck | 14,2318 |
| BCS Class | 1 |
| Stability: | Hygroscopic |
| InChI | InChI=1S/C20H21FN2O.C2H2O4/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;3-1(4)2(5)6/h4-9,12H,3,10-11,14H2,1-2H3;(H,3,4)(H,5,6) |
| InChIKey | KTGRHKOEFSJQNS-UHFFFAOYSA-N |
| SMILES | C1(CCCN(C)C)(C2=CC=C(F)C=C2)C2=C(C=C(C#N)C=C2)CO1.C(O)(=O)C(O)=O |
| CAS DataBase Reference | 219861-08-2(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| RTECS | NP6333500 |
| HS Code | 29322090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Dermal
Acute Tox. 4 Oral |
Escitalopram oxalate Usage And Synthesis
| Description | Escitalopram was launched as Cipralex? in Switzerland, Sweden and UK forthetreatment of depression and panic disorder. It is the S-enantiomer version of theselective serotonin reuptake inhibitor (SSRI) citalopram approved in 1989. It can beobtained from 5cyanophthalide by successive reactions with 4-fluorophenyl magnesiumbromide and 3-(dimethylamino)propyl magnesium chloride. The resulting racemic diol canbe resolved by several routes such as crystallization with a chiral acid. Finally, a two stepcyclisation procedure affords escitalopram. Escitalopram is twice as effective as theracemate and over 100 fold more potent than the R-enantiomer in inhibiting the 5HTreuptake in vivo in rat brain synaptosomes. Moreover, it exhibits higher selectivity for thehuman serotonin transporter relative to the noradrenaline or dopamine transporters thanany other currently available SSRl’s. In the mouse forced swim test, the duration ofimmobility (which reflects antidepressant activity) for escitalopram was comparable tocitalopram and greater than (R)-citalopram. Clinical trials in patients with panic disorders ordepression have shown that escitalopram has a clinically relevant and significant effect.Additionally, it has a faster onset of antidepressant action than citalopram. Escitalopramhas linear pharmacokinetics, with a long half-life (27-32 h). It is extensively metabolized inthe 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 drugmetabolizingenzymes in vitro. Escitalopram is well tolerated with nausea being the mostcommon side effect. |
| Chemical Properties | White Solid |
| Originator | Lundbeck (Denmark) |
| Uses | Escitalopram oxalate may be used as a pharmaceutical primary standard for the quantification of the analyte in pharmaceutical formulations using analytical techniques. |
| Uses | A labelled inhibitor of serotonin (5-HT) uptake. Antidepressant |
| Brand name | Lexapro (Forest). |
| General Description | Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Escitalopram Oxalate, a highly selective serotonin re-uptake inhibitor antidepressant, is a pure S-enantiomer of the racemic, bicyclic pthalates derivatives of citalopram. It is mainly developed for the treatment of depression and anxiety disorders. |
| Biochem/physiol Actions | Escitalopram is a selective serotonin reuptake inhibitor (SSRI), the S-enantiomer and eutomer of citalopram. |
| Mechanism of action | Escitalopram is the S-enantiomer of citalopram and is the most selective of SSRIs. SSRIs' mechanism of action is exerted by binding to the sodium-dependant serotonin transporter protein (SERT) located in the presynaptic neuron. SERT works by re-uptaking serotonin from the synaptic cleft to the presynaptic neuron. When SERT is inactivated by escitalopram, this increases the amount of serotonin in the synaptic cleft. |
| Side effects | The main side effect of escitalopram include: Nausea, dry mouth, trouble sleeping, constipation, tiredness, drowsiness, dizziness, and increased sweating may occur. |
| Synthesis | The synthesis of escitalopram was carried out in severaldifferent routes [30-33]. 5-Cyanophthalide (72) was treatedwith Grignard reagent 73 at 0??C to provide intermediate 75which was reacted in situ with another Grignard reagent 76to afford the diol in a one-pot process. Racemic diol 77 wasresolved using (+)-p-toluoyltartaric acid to afford desired Sisomer 78 in 55% yield. The ring closure reaction wascarried out at 0??C using methanesulfonyl chloride in tolueneto furnish escitalopram (7) in 60% yield. |
| storage | +4°C |
| references | [1] sánchez c1, bergqvist pb, brennum lt, gupta s, hogg s, larsen a, wiborg o. escitalopram, the s-(+)-enantiomer of citalopram, is a selective serotonin reuptake inhibitor with potent effects in animal models predictive of antidepressant and anxiolytic activities. psychopharmacology (berl). 2003 jun;167(4):353-62. epub 2003 apr 26. |
Escitalopram oxalate Preparation Products And Raw materials
| Raw materials | (-)-4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile-->Escitalopram-->Oxalic acid |
