ドンペリドン
Domperidone
基本情報
- CAS
57808-66-9- 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
domperidone57808-66-9MotiliumDomperidonaDomperidonumR 33,812R-33812NSC299589NSC-299589DTXSID1045116KW 5338NSC-759575
名称をさらに表示
エボキシンドンペリドンドメピリドンペリゼリンエボキシン【アルカロイド】ハドドリンミオナゼリンドンペネマドンペリン-DSドンペリンアースレナンジャックマールフォリメジンノーゼアモンロビアペリドンナウゼリンセロベースナシロビンダリックDOMPERIDONE BASEDomperidonDomperidone powderkw-53385-chloro-1-{1-[3-(2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)propyl]piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-onegjEvoxinEucitonPeridon
5-Chloro-1-(1-(3-(2-oxo-1-benzimidazolinyl)propyl)-4-piperidyl)-2-benzimidazolinone6-chloro-3-[1-[3-(2-oxo-3H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1H-benzimidazol-2-oneDTXCID9025116CHEBI:315155-Chloro-1-[1-[3-(2-oxo-1-benzimidazolinyl)propyl]-4-piperidyl]-2-benzimidazolinoneApo Domperidone5587267Z692H-Benzimidazol-2-one, 5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl)-4-piperidinyl)-1,3-dihydro-
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)
Human DrugsBreast Feeding; Lactation; Milk, Human; Antiemetics; Dopamine Antagonists; Galactogogues; Gastrointestinal Agents
Animal DrugsActive Ingredients (domperidone) -> FDA Greenbook
Melting Point242.5 °C
Physical DescriptionSolid
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
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
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
Other Safety InformationIMAP assessments - 2H-Benzimidazol-2-one, 5-chloro-1-[1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl]-1,3-dihydro-: Human health tier I assessment
Hazard Classes and CategoriesRepr. 2 (89.8%)
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
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
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
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
Protein Binding91%-93%
PharmacodynamicsDomperidone is a specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.
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
Biological Half-Life7 hours
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.
関連反応
32 件
化合物ノート
読み込み中…