CAS 219861-08-2 Escitalopram Oxalate (HCID 146571)

Names & identifiers

Preferred name: Escitalopram Oxalate
IUPAC: (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;oxalic acid
English name: Escitalopram oxalate
Molecular formula: C22H23FN2O5
Molecular weight: 414.43

Names & synonyms

Escitalopram oxalate219861-08-2DTXSID1046003Escitalopram (as oxalate)Lu 26-054-0Citalopram oxalate, (s)-5U85DBW7LONSC-758934Lu-26-054-0LU-26-054-ODTXCID9026003Escitslopram

Show more names

CipralexescitalopraM oxalat(S)-Citalopram-d6 Oxalate(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile(1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile EthanedioateCS-323(S)-CITALOPRAMEscitalopraM API(S)-Citalopram-d6ESCIFALOPRAMOXALATE

Escitalopram OralRefChem:56379Escitalopram Oral Solution5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-,(1S)-, ethanedioate(1:1)Lexapro(S)-Citalopram Oxalate(S)-(+)Citalopram oxalateEscitalopram (oxalate)

Database identifiers

CAS: 219861-08-2
PubChem CID: 146571
DTXSID: DTXSID1046003
ChEMBL: CHEMBL1200322
UNII: 5U85DBW7LO
EC Number: 620-544-8

Properties

Computed structural properties

Topological polar surface area: 111 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 8
Rotatable bonds: 6
Heavy atoms: 30
Formal charge: 0
Complexity: 537

Experimental & physicochemical properties

Collision Cross Section178.8 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 152 · 152-153°C
alpha: 12.31 ° · D +12.31° (c = 1 in methanol)
storage temp.: 2 · 2-8°C
solubility: 15 mg/mL · DMSO: ≥15mg/mL
form: powder
pka: 4.19 · 4.19 (acid)
color: white to tan
Merck: 14 · 14,2318
BCS Class: 1 · 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 · 219861-08-2(CAS DataBase Reference)
FDA UNII: 5 U85DBW7LO · 5U85DBW7LO
NCI Drug Dictionary: escitalopram oxalate
UNSPSC Code: 41116107 · 41116107
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
RTECS: 6333500 · NP6333500
HS Code: 29322090 · 29322090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 Oral

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (14.9%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (88.1%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (86.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (86.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (14.9%)；Skin Irrit. 2 (88.1%)；Eye Irrit. 2 (86.6%)；STOT SE 3 (86.6%)

Toxicology

Treatment · 1 item

Establish and maintain an airway to ensure adequate ventilation and oxygenation. Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are recommended, along with general symptomatic and supportive care. Due to the large volume of distribution of escitalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. There are no specific antidotes for Escitalopram. (L1712)

Exposure RoutesThe absolute bioavailability of citalopram is about 80% relative to an intravenous dose.

Toxicity Summary · 1 item

The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Escitalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.

Signs and SymptomsSigns of overdose include convulsions, coma, dizziness, hypotension, insomnia, nausea, vomiting, sinus tachycardia, somnolence, and ECG changes (including QT prolongation).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Escitalopram oxalate

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk: 3
rtecs: NP6333500
hs_code: 29322090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 Oral
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Mainly hepatic. Escitalopram undergoes N-demethylation to S-demethylcitalopram (S-DCT) and S-didemethylcitalopram (S-DDCT). CYP3A4 and CYP2C19 are the enzymes responsible for this N-demethylation reaction. Route of Elimination: Following oral administrations of escitalopram, the fraction of drug recovered in the urine as escitalopram and S-demethylcitalopram (S-DCT) is about 8% and 10%, respectively. The oral clearance of escitalopram is 600 mL/min, with approximately 7% of that due to renal clearance. Escitalopram is metabolized to S-DCT and S-didemethylcitalopram (S-DDCT). Half Life: 27-32 hours

FDA Pharmacological Classification · 6 items

ESCITALOPRAM ORAL

Serotonin Reuptake Inhibitor [EPC]; Serotonin Uptake Inhibitors [MoA]

ESCITALOPRAM OXALATE

Serotonin Uptake Inhibitors [MoA]; Serotonin Reuptake Inhibitor [EPC]

ESCITSLOPRAM

Serotonin Reuptake Inhibitor [EPC]; Serotonin Uptake Inhibitors [MoA]

MeSH Pharmacological ClassificationCompounds that specifically inhibit the reuptake of serotonin in the brain.

Uses & manufacturing

UsesLabeled indications include major depressive disorder (MDD) and generalized anxiety disorder (GAD). Unlabeled indications include treatment of mild dementia-associated agitation in nonpsychotic patients.

Applications · 4 items

DescriptionEscitalopram 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.

UsesEscitalopram oxalate may be used as a pharmaceutical primary standard for the quantification of the analyte in pharmaceutical formulations using analytical techniques.

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

General DescriptionPharmaceutical 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.