Escitalopram Oxalate (HCID 146571)

名称と識別子

優先名称: Escitalopram Oxalate
IUPAC: (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;oxalic acid
現地名: (S)-シタロプラムしゅう酸塩
英語名: Escitalopram oxalate
分子式: C22H23FN2O5
分子量: 414.43

名称と別名

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

名称をさらに表示

(S)-シタロプラムしゅう酸塩(S)-1-[3-(ジメチルアミノ)プロピル]-1-(4-フルオロフェニル)-1,3-ジヒドロイソベンゾフラン-5-カルボニトリルしゅう酸塩エスシタロプラムしゅう酸塩しゅう酸(S)-シタロプラムエスシタロプラムシュウ酸塩エスシタロプラムシュウ酸塩 (JAN)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)

データベース識別子

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

物性

構造計算による物性

極性表面積: 111 Å²
水素結合供与体数: 2
水素結合受容体数: 8
回転可能結合数: 6
重原子数: 30
形式電荷: 0
複雑度: 537

実験および物理化学的性質

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

物理化学的性質

融点: 152 · 152-153°C
比旋光度: 12.31 ° · D +12.31° (c = 1 in methanol)
貯蔵温度: 2 · 2-8°C
溶解性: 15 mg/mL以上 · DMSO：15mg/mL以上
外見: 粉
酸解離定数(Pka): 4.19 · 4.19 (acid)
色: 白から黄褐色
Merck: 14 · 14,2318
BCS Class: 1 · 1
安定性: 吸湿性
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 データベース: 219861 · 219861-08-2(CAS DataBase Reference)

化学的性質

化学的特性White Solid

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

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

毒性情報

Treatment · 1 件

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 件

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 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Escitalopram oxalate

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

安全データ

wgk: 3
rtecs: NP6333500
hs_code: 29322090
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
毒劇物取締法: 劇物
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 Oral
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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 件

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.

用途と製造

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

応用分野 · 3 件

説明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.

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

一般的な説明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.