ChemicalBook > CAS DataBase List > Escitalopram oxalate

Escitalopram oxalate

Product Name
Escitalopram oxalate
CAS No.
219861-08-2
Chemical Name
Escitalopram oxalate
Synonyms
Cipralex;escitalopraM oxalat;(S)-Citalopram-d6 Oxalate;(1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Ethanedioate;CS-323;(S)-CITALOPRAM;EscitalopraM API;(S)-Citalopram-d6;ESCIFALOPRAMOXALATE;CitalopraM S-IsoMer
CBNumber
CB5712919
Molecular Formula
C22H23FN2O5
Formula Weight
414.43
MOL File
219861-08-2.mol
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Escitalopram oxalate Property

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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
NP6333500
HS Code 
29322090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
E4786
Product name
Escitalopram oxalate
Purity
≥98% (HPLC), powder
Packaging
10mg
Price
$92.7
Updated
2024/03/01
Sigma-Aldrich
Product number
1249406
Product name
Escitalopram oxalate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$1230
Updated
2024/03/01
TCI Chemical
Product number
E0958
Product name
(S)-Citalopram Oxalate
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$235
Updated
2024/03/01
TCI Chemical
Product number
E0958
Product name
(S)-Citalopram Oxalate
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$68
Updated
2024/03/01
Sigma-Aldrich
Product number
Y0001797
Product name
Escitalopram for system suitability
Purity
EuropePharmacopoeia (EP) Reference Standard
Packaging
y0001797
Price
$223
Updated
2024/03/01
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Escitalopram oxalate Chemical Properties,Usage,Production

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.

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 several different routes [30-33]. 5-Cyanophthalide (72) was treated with Grignard reagent 73 at 0??C to provide intermediate 75 which was reacted in situ with another Grignard reagent 76 to afford the diol in a one-pot process. Racemic diol 77 was resolved using (+)-p-toluoyltartaric acid to afford desired S isomer 78 in 55% yield. The ring closure reaction was carried out at 0??C using methanesulfonyl chloride in toluene to 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

Preparation Products

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Escitalopram oxalate Suppliers

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View Lastest Price from Escitalopram oxalate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Escitalopram oxalate 219861-08-2
Price
US $0.00/KG
Min. Order
1KG
Purity
98.0%~102.0%; USP40
Supply Ability
1800kg/month
Release date
2021-06-03
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Escitalopram oxalate 219861-08-2
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98%-102% USP
Supply Ability
100kg
Release date
2021-11-03
Hebei Chuanghai Biotechnology Co,.LTD
Product
Escitalopram Oxalate 219861-08-2
Price
US $11.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000kg
Release date
2024-08-21

219861-08-2, Escitalopram oxalateRelated Search:

Citalopram Triphenylphosphine Propyl butyrate 3-Dimethylaminopropylamine Nitrofurantoin Propyl gallate 2-Phenylphenol Citalopram hydrobromide Calcium oxalate Basic Green 4 FURFURYL ALCOHOL RESIN Shikimic acid Escitalopram Furazolidone Tetrahydrofuran Ferrous oxalate Phenylacetone Carbofuran

  • (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
  • (1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Ethanedioate
  • Cipralex
  • (S)-Citalopram-d6 Oxalate
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  • Escitaloptam-d4 Oxalate
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  • Citalopram Impurity 2((S)-Isomer)
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  • Escitalopram Oxalate (200 mg)
  • (1S)-1-[3-(diMethylaMino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
  • EscitalopraM oxalate S-(+)-CITAPROLAM OXALATE
  • (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
  • (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-isobenzofuran-5-carbonitrile
  • CitalopraM S-IsoMer
  • escitalopraM oxalat
  • EscitalopraM API
  • D-citalopraM oxalate
  • 5-Isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (1S)-, ethanedioate (1:1)
  • S-(+)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile oxalate
  • (S)-Escitalopram Oxalate
  • Escitalopram oxalate, >=98%
  • CS-323
  • [2H4]-Escitalopram Oxalate
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  • Escitalopram D3 oxalateQ: What is Escitalopram D3 oxalate Q: What is the CAS Number of Escitalopram D3 oxalate Q: What is the storage condition of Escitalopram D3 oxalate Q: What are the applications of Escitalopram D3 oxalate
  • Escitalopram Oxalate(Secondary Standards traceble to USP)
  • Escitalopram oxalateQ: What is Escitalopram oxalate Q: What is the CAS Number of Escitalopram oxalate Q: What is the storage condition of Escitalopram oxalate Q: What are the applications of Escitalopram oxalate
  • Escitalopram Oxalate (1249406)
  • Dexcitalopram oxalate
  • Escitalopram Oxalatea
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  • Escitalopram oxalate API
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  • 219861-08-2
  • 128196-0-0
  • C20H21FN20C2H2O4