Escitalopram Oxalate
Grundinformationen
- CAS
219861-08-2- 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
- Monoisotopische Masse
- 414,1591
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
- Escitalopram 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
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 OralEscitalopram Oral SolutionRefChem:563795-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-,(1S)-, ethanedioate(1:1)Lexapro(S)-Citalopram Oxalate(S)-(+)Citalopram oxalateEscitalopram (oxalate)
Eigenschaften
Berechnete Struktureigenschaften
- 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
- Schmelzpunkt
- 152 · 152-153°C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 15 mg/mL · DMSO: ≥15mg/mL
- Aggregatzustand
- powder
- pka
- 4.19 · 4.19 (acid)
- Farbe
- white to tan
- Merck
- 14 · 14,2318
- BCS Class
- 1 · 1
- Stabilität
- 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
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.
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
BeschreibungEscitalopram 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.
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