Escitalopram Oxalate
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Grundinformationen
- CAS
1217733-09-9- Standard-SMILES
CN(C)CCC[C@@]1(c2ccc(F)cc2)OCc2cc(C#N)ccc21.O=C(O)C(=O)O- InChIKey
KTGRHKOEFSJQNS-BDQAORGHSA-N- Summenformel
- C22H23FN2O5
- Durchschnittliche Molmasse
- 414,4 g/mol
Überblick
Escitalopram Oxalate is the oxalate salt of escitalopram, a pure S-enantiomer of the racemic bicyclic phthalane derivative citalopram, with antidepressant activity. As a selective serotonin reuptake inhibitor (SSRI), escitalopram blocks the reuptake of serotonin by neurons in the central nervous system (CNS), thereby potentiating CNS serotonergic activity.
Namen und Bezeichner
- Bevorzugter Name
- Escitalopram Oxalate
- IUPAC
- (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;oxalic acid
- Englischer Name
- (S)-Citalopram-d6 Oxalate
- Summenformel
- C22H23FN2O5
- Molmasse
- 414.43
Namen und Synonyme
Escitalopram oxalate219861-08-2DTXSID1046003Escitalopram (as oxalate)Lu 26-054-0Citalopram oxalate, (s)-5U85DBW7LONSC-758934Lu-26-054-0LU-26-054-ODTXCID9026003Escitslopram
Weitere Namen anzeigen
D6- (S)-Citalopram Oxalate[2H6]- (S)-Citalopram Oxalate
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)
Datenbank-Bezeichner
- CAS
1217733-09-9- ChEMBL
CHEMBL1200322- UNII
- 5U85DBW7LO
- EC Number
- 620-544-8
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- Polarare Oberfläche (TPSA)
- 111 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 537
Experimentelle und physikochemische Eigenschaften
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section178.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Stabilität
- Hygroscopic
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (14.9%): Harmful if swallowed [Warning Acute toxicity, oral]
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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (14.9%)
Toxikologische Informationen
Treatment
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
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 5HT<sub>1A</sub> 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
Drug Induced Liver Injury Rank (DILIrank 2.0)
Escitalopram oxalate
vLess-DILI-concern
7
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Mainly hepatic. Escitalopram undergoes <i>N</i>-demethylation to <i>S</i>-demethylcitalopram (S-DCT) and <i>S</i>-didemethylcitalopram (S-DDCT). CYP3A4 and CYP2C19 are the enzymes responsible for this <i>N</i>-demethylation reaction. Route of Elimination: Following oral administrations of escitalopram, the fraction of drug recovered in the urine as escitalopram and <i>S</i>-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 <i>S</i>-didemethylcitalopram (S-DDCT). Half Life: 27-32 hours
FDA Pharmacological Classification
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.
Verwendung und Herstellung
UsesLabeled indications include major depressive disorder (MDD) and generalized anxiety disorder (GAD). Unlabeled indications include treatment of mild dementia-associated agitation in nonpsychotic patients.
Anwendungen
VerwendenA labelled inhibitor of serotonin (5-HT) uptake. Antidepressant.
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