Domperidone
기본 정보
- CAS
57808-66-9- 표준 SMILES
O=c1[nH]c2ccccc2n1CCCN1CCC(n2c(=O)[nH]c3cc(Cl)ccc32)CC1- InChIKey
FGXWKSZFVQUSTL-UHFFFAOYSA-N- 분자식
- C22H24ClN5O2
- 평균 분자량
- 425.9 g/mol
- 단동위원소 질량
- 425.16185269
개요
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.
이름 및 식별자
- 우선 이름
- Domperidone
- IUPAC
- 6-chloro-3-[1-[3-(2-oxo-3H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1H-benzimidazol-2-one
- 영어명
- Domperidone
- 분자식
- C22H24ClN5O2
- 분자량
- 425.91
이름 및 동의어
domperidone57808-66-9MotiliumDomperidonaDomperidonumR 33,812R-33812NSC299589NSC-299589DTXSID1045116KW 5338NSC-759575
이름 더 보기
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-
데이터베이스 식별자
- CAS
57808-66-9- PubChem CID
- 3151
- DTXSID
DTXSID1045116- ChEMBL
CHEMBL219916- ChEBI
CHEBI:31515- UNII
- 5587267Z69
- EC Number
- 260-968-7
- Nikkaji
- J3.199B
물성
구조 계산 물성
- XLogP
- 3.9
- 극성 표면적
- 67.9 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 30
- 형식 전하
- 0
- 복잡도
- 655
실험 및 물리화학적 성질
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]
물리화학적 성질
- 녹는점
- 240 · 240-244°C
- 밀도
- 1.2904 · 1.2904 (rough estimate)
- 굴절률
- 1.54 · 1.5400 (estimate)
- 저장 조건
- Store at RT
- 용해도
- 10 mg/mL · DMSO: >10mg/mL
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 7.9 · pKa 7.90 (Uncertain)
- 색상
- 하얀색
- 수용성
- 물에 약간 용해됩니다.
- Merck
- 14 · 14,3418
- 안정성
- 안정적인. 강한 산화제와 호환되지 않습니다.
- 주요 응용
- 의약품(소분자)
- 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
화학적 성질
White or almost white powder.
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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.
유해성 정보
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%)
독성 정보
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
안전 데이터
- wgk
- 3
- rtecs
- DE2275900
- HS 번호
- 29333990
- risk_code
- 62-63
- hazard_code
- Xn
- safety_code
- 26-36
- 기존화학 물질
- KE-05607
- Hazard Classifications
- Repr. 2
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
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.
Cellular LocationsMembrane
용도 및 제조
UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
응용 분야
용도A 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.
상·하류 제품 정보
상류 원료
추가 설명
정의ChEBI: 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.
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32건
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