基本情報
- 標準SMILES
O=c1[nH]c2ccccc2n1CCCN1CCC(n2c(=O)[nH]c3cc(Cl)ccc32)CC1- InChIKey
FGXWKSZFVQUSTL-UHFFFAOYSA-N- 分子式
- C22H24ClN5O2
- 平均分子量
- 425.9 g/mol
- 単同位体質量
- 425.16185269
概要
Domperidone is 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used as an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet preparations. It has a role as a dopaminergic antagonist and an antiemetic. It is a member of benzimidazoles and a heteroarylpiperidine.
名称と識別子
- 優先名称
- Domperidone
- IUPAC
- 6-chloro-3-[1-[3-(2-oxo-3H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1H-benzimidazol-2-one
- 現地名
- ドンペリドン
- 英語名
- Domperidone
- 分子式
- C22H24ClN5O2
- 分子量
- 425.91
名称と別名
名称をさらに表示
データベース識別子
- CAS
57808-66-9- PubChem CID
- 3151
- DTXSID
DTXSID1045116- ChEMBL
CHEMBL219916- ChEBI
CHEBI:31515- UNII
- 5587267Z69
- EC Number
- 260-968-7
- Nikkaji
- J3.199B
物性
構造計算による物性
- XLogP
- 3.9
- 極性表面積
- 67.9 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 5
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 655
実験および物理化学的性質
Drugs
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
LogP
2.4
3.45
Solubility
9.25e-02 g/L
50.4 [ug/mL] (The mean of the results at pH 7.4)
Dissociation Constants
7.9
7.9
Collision Cross Section
201.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
199.16 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 240 · 240-244°C
- 比重(密度)
- 1.2904 · 1.2904 (rough estimate)
- 屈折率
- 1.54 · 1.5400 (estimate)
- 貯蔵温度
- Store at RT
- 溶解性
- 10 mg/mL · DMSO: >10 mg/mL
- 外見
- 個体
- 酸解離定数(Pka)
- 7.9 · pKa 7.90 (Uncertain)
- 色
- 白い
- 水溶解度
- 水にわずかに溶ける。
- Merck
- 14 · 14,3418
- 安定性
- 安定。強力な酸化剤とは相容れない。
- 主な用途
- 医薬品(低分子化合物)
- InChI
- 1S/C22H24ClN5O2/c23-15-6-7-20-18(14-15)25-22(30)28(20)16-8-12-26(13-9-16)10-3-11-27-19-5-2-1-4-17(19)24-21(27)29/h1-2,4-7,14,16H,3,8-13H2,(H,24,29)(H,25,30)
- InChIKey
- FGXWKSZFVQUSTL-UHFFFAOYSA-N
- SMILES
- C1(=O)N(C2CCN(CCCN3C(=O)NC4=CC=CC=C43)CC2)C2=CC=C(Cl)C=C2N1
- CAS データベース
- 57808 · 57808-66-9(CAS DataBase Reference)
化学的性質
化学的特性White or almost white powder.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 0.9% (1 of 108) of reports.
Warning
H361 (89.8%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 108 reports by companies from 6 notifications to the ECHA C&L Inventory.
危険有害性情報
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Domperidone
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
安全データ
- wgk
- 3
- rtecs
- DE2275900
- hs_code
- 29333990
- risk_code
- 62-63
- hazard_code
- Xn
- safety_code
- 26-36
- Hazard Classifications
- Repr. 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
A03FA03
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
QP - Antiparasitic products, insecticides and repellents
Mechanism of Action
Domperidone acts as a gastrointestinal emptying (delayed) adjunct and peristaltic stimulant. The gastroprokinetic properties of domperidone are related to its peripheral dopamine receptor blocking properties. Domperidone facilitates gastric emptying and decreases small bowel transit time by increasing esophageal and gastric peristalsis and by lowering esophageal sphincter pressure. Antiemetic: The antiemetic properties of domperidone are related to its dopamine receptor blocking activity at both the chemoreceptor trigger zone and at the gastric level. It has strong affinities for the D2 and D3 dopamine receptors, which are found in the chemoreceptor trigger zone, located just outside the blood brain barrier, which - among others - regulates nausea and vomiting
Metabolism/Metabolites
Domperidone has known human metabolites that include 5-Chloro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one, 1-Propyl-1,3-dihydro-2H-benzimidazol-2-one, and 3-[3-[4-(5-Chloro-2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]propyl]-6-hydroxy-1H-benzimidazol-2-one.
MeSH Pharmacological Classification
Drugs used to prevent NAUSEA or VOMITING.
Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.
用途と製造
応用分野
用途ドンペリドンはこのD2受容体への拮抗作用により吐き気を抑え、上部消化管の運動機能を調整(促進)する。
用途ドンペリドン(英: Domperidone)は、ドーパミン受容体拮抗薬の一つで、制吐薬、消化管機能改善薬として利用されている。
用途ドパミンD2 受容体遮断作用 を示します。
使用A novel peripheral dopamine receptor antagonist that does not cross the blood-brain barrier; anti-emetic. Domperidone(Motilium) is a dopamine blocker and an antidopaminergic reagent.
上流・下流製品情報
上流原料
サプライヤー50 社
補足説明
定義ChEBI: 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used s an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet reparations.
関連反応
関連ノート
読み込み中…