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Domperidon

Domperidone

HCID 3151
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Grundinformationen

CAS
57808-66-9
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

domperidone57808-66-9MotiliumDomperidonaDomperidonumR 33,812R-33812NSC299589NSC-299589DTXSID1045116KW 5338NSC-759575
Weitere Namen anzeigen
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-

Datenbank-Bezeichner

CAS

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 · 3 Einträge

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP · 2 Einträge

2.4

3.45

Solubility · 2 Einträge

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 · 2 Einträge

7.9

7.9

Collision Cross Section · 2 Einträge

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

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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

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%)

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

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

Sicherheitsdaten

wgk
3
hs_code
29333990
RTECS-Nr.
DE2275900
risk_code
62-63
hazard_code
Xn

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

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 · 1 Eintrag

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 · 1 Eintrag

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 · 2 Einträge

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.

Zugehörige Reaktionen

32
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 46877
HRID 46877als Produktuspto-grants-1979_11
Reaktionsgleichung von HRID 46881
HRID 46881als Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 46884
HRID 46884als Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 46885
HRID 46885als Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 46917
HRID 46917als Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 971757
HRID 971757als Produktuspto-grants-1979_07
Reaktionsgleichung von HRID 971761
HRID 971761als Eduktuspto-grants-1979_07
Reaktionsgleichung von HRID 971763
HRID 971763als Eduktuspto-grants-1979_07
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Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
57808-66-9
PubChem CID
3151
DTXSID
DTXSID1045116
ChEMBL
CHEMBL219916
ChEBI
CHEBI:31515
UNII
5587267Z69
EC Number
260-968-7
Nikkaji
J3.199B

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)
safety_code
26-36
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Repr. 2
Cellular LocationsMembrane

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

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

Silica gelBenzimidazol1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl esterN,N-DimethylformamidKaliumiodid1-Chlor-2-nitrobenzolHydroxypropylTrichlormethan4-Aminocyclohexanecarboxylic acid4-Methylpentan-2-onKaliumcyanid5-Chloro-1,3-benzodioxole
Ergänzende Hinweise · 1 Eintrag

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.