Home Categories API (S)-Citalopram-d6Oxalate
A0364156

(S)-Citalopram-d6Oxalate

Synonym(s):
Escitalopram oxalate;S-(+)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile oxalate;S-(+)-Citalopram oxalate

CAS NO.:

Empirical Formula: C22H23FN2O5

Molecular Weight: 414.43

MDL number: MFCD06407826

EINECS: 620-544-8

Pack Size Price Stock Quantity
1mg RMB2436.80 In Stock
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Update time: 2022-07-08

PRODUCT 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

Description and Uses

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.

A labelled inhibitor of serotonin (5-HT) uptake. Antidepressant

Safety

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  NP6333500
HS Code  29322090

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