Grundinformationen
- Standard-SMILES
O=c1[nH]c2ccccc2n1CCCN1CCC(n2c(=O)[nH]c3cc(Cl)ccc32)CC1- InChIKey
FGXWKSZFVQUSTL-UHFFFAOYSA-N- Summenformel
- C22H24ClN5O2
- Durchschnittliche Molmasse
- 425,9 g/mol
- Monoisotopische Masse
- 425,16185269
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Domperidone
- IUPAC
- 6-chloro-3-[1-[3-(2-oxo-3H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1H-benzimidazol-2-one
- Lokaler Name
- Domperidon
- Englischer Name
- Domperidone
- Summenformel
- C22H24ClN5O2
- Molmasse
- 425.91
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
57808-66-9- PubChem CID
- 3151
- DTXSID
DTXSID1045116- ChEMBL
CHEMBL219916- ChEBI
CHEBI:31515- UNII
- 5587267Z69
- EC Number
- 260-968-7
- Nikkaji
- J3.199B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,9
- Polarare Oberfläche (TPSA)
- 67,9 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 655
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 240 · 240-244°C
- Dichte
- 1.2904 · 1.2904 (rough estimate)
- Brechungsindex
- 1.54 · 1.5400 (estimate)
- storage temp.
- Store at RT
- Löslichkeit
- 10 mg/mL · DMSO: >10 mg/mL
- Aggregatzustand
- solid
- pka
- 7.9 · pKa 7.90 (Uncertain)
- Farbe
- white
- Wasserlöslichkeit
- Slightly soluble in water.
- Merck
- 14 · 14,3418
- Stabilität
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- pharmaceutical (small molecule)
- 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 Datenbank
- 57808 · 57808-66-9(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Domperidone
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29333990
- RTECS-Nr.
- DE2275900
- risk_code
- 62-63
- hazard_code
- Xn
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Repr. 2
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
Anwendungen
VerwendenA 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: 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.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…