CAS 87051-43-2 Ritanserin (HCID 5074)

概要

Ritanserin is a thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action. It has a role as an antidepressant, an anxiolytic drug, an antipsychotic agent, a serotonergic antagonist, a dopaminergic antagonist and an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor. It is a member of piperidines, an organofluorine compound and a thiazolopyrimidine.

名称と識別子

優先名称: Ritanserin
IUPAC: 6-[2-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one
現地名: リタンセリン
英語名: Ritanserin
分子式: C27H25F2N3OS
分子量: 477.57

名称と別名

ritanserin87051-43-2TisertonRitanserinaRitanserineRitanserinumR-55667R 55,667DTXSID9042594NSC-7584706-(2-(4-(Bis(p-fluorophenyl)methylene)-piperidino)ethyl)-7-methyl-5H-thiazolo-(3,2-a)pyrimidin-5-one145TFV465S

名称をさらに表示

6-[2-[4-(4,4'-ジフルオロベンズヒドリリデン)ピペリジノ]エチル]-7-メチル-5H-チアゾロ[3,2-a]ピリミジン-5-オン6-[2-[4-[ビス(4-フルオロフェニル)メチレン]ピペリジン-1-イル]エチル]-7-メチル-5H-チアゾロ[3,2-a]ピリミジン-5-オンリタンセリン6-[2-[4-(4,4′-ジフルオロベンズヒドリリデン)ピペリジノ]エチル]-7-メチル-5H-チアゾロ[3,2-a]ピリミジン-5-オン6-(2-{4-[ビス(4-フルオロフェニル)メチリデン]ピペリジン-1-イル}エチル)-7-メチル-5H-[1,3]チアゾロ[3,2-a]ピリミジン-5-オンR 55667CamibirstatRitanserin（R 55667）Ritanserin, 10 mM in DMSORITANSERIN SEROTONIN ANTAGONIST6-[2-[4-[Bis(4-fluorophenyl)Methylidene]piperidin-1-yl]ethyl]-7-Methyl-[1,3]thia6-(2-(4-(Bis(4-fluorophenyl)methylene)piperidin-1-yl)-ethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimi6-[2-[4-[BIS(4-FLUOROPHENYL)-METHYLENE]-1-PIPERIDINYL]-ETHYL]-5H-THIAZOLO[3,2-A]PYRIMIDIN-5-ONE

6-(2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneDTXCID7022594CHEBI:641955H-Thiazolo(3,2-a)pyrimidin-5-one, 6-(2-(4-bis(4-fluorophenyl)methylene)-1-piperidinyl)ethyl)-7-methyl-6-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one6-[2-[4-(bis(4-Fluorophenyl)methylene]-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one6-[2-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-7-methyl-[1,3]thiazolo[2,3-b]pyrimidin-5-one5H-Thiazolo[3,2-a]pyrimidin-5-one, 6-[2-[4-bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-7-methyl-

データベース識別子

CAS: 87051-43-2
PubChem CID: 5074
DTXSID: DTXSID9042594
ChEMBL: CHEMBL267777
ChEBI: CHEBI:64195
UNII: 145TFV465S
EC Number: 635-929-6
Nikkaji: J23.318H

物性

構造計算による物性

XLogP: 5.2
極性表面積: 61.2 Å²
水素結合供与体数: 0
水素結合受容体数: 6
回転可能結合数: 5
重原子数: 34
形式電荷: 0
複雑度: 877

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Solubility12.2 [ug/mL] (The mean of the results at pH 7.4)

Collision Cross Section · 2 件

219.86 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

220.7 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 145.5 ° · 145.5°
沸点: 618.7 · 618.7±65.0 °C(Predicted)
比重(密度): 1.3 · 1.30±0.1 g/cm3(Predicted)
貯蔵温度: 2 · Sealed in dry,2-8°C
溶解性: 10 mg/mL · メタノール: >10 mg/mL
外見: 個体
酸解離定数(Pka): 7.74 · 7.74±0.20(Predicted)
色: 白い
InChI: 1S/C27H25F2N3OS/c1-18-24(26(33)32-16-17-34-27(32)30-18)12-15-31-13-10-21(11-14-31)25(19-2-6-22(28)7-3-19)20-4-8-23(29)9-5-20/h2-9,16-17H,10-15H2,1H3
InChIKey: JUQLTPCYUFPYKE-UHFFFAOYSA-N
SMILES: CC1=C(CCN2CCC(\CC2)=C(\c3ccc(F)cc3)c4ccc(F)cc4)C(=O)N5C=CSC5=N1

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Other Safety InformationIMAP assessments - 5H-Thiazolo[3,2-a]pyrimidin-5-one, 6-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-7-methyl-: Environment tier I assessment

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

wgk: 3
毒性: LD50 in male, female mice, rats, dogs (mg/kg): 28.2, 28.2, 20.0, 22.2, 24.1, 33.2 i.v.; 626, 993, 956, 515, ~1280, 640-1280 orally (Awouters)
risk_code: 36/37/38
hazard_code: Xi
safety_code: 22-26-36
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

MeSH Pharmacological Classification · 4 件

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.

応用分野 · 3 件

説明Ritanserin, also known by its developmental code name R-55667, is a serotonin antagonist medication described as an anxiolytic, antidepressant, antiparkinsonian agent, and antihypertensive agent. It was never marketed for medical use due to safety problems but has been used in scientific research to study the serotonin system.

使用Ritanserin has been used in behavioral testing and as a serotonin 2A receptor (5-HT2A)-receptor antagonist.

使用Ritanserin and other 5HT2A/2C receptor antagonists have shown in clinical trial to promote slow-wave sleep in chronic primary insomnia or generalized anxiety disorder (Mayer, 2003).

サプライヤー43 社

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補足説明 · 1 件

定義ChEBI: Ritanserin is a thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action. It has a role as a dopaminergic antagonist, a serotonergic antagonist, an antipsychotic agent, an anxiolytic drug, an antidepressant and an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor. It is an organofluorine compound, a member of piperidines and a thiazolopyrimidine.