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Domperidone

HCID 3151
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Basic information

CAS
57808-66-9
Standard SMILES
O=c1[nH]c2ccccc2n1CCCN1CCC(n2c(=O)[nH]c3cc(Cl)ccc32)CC1
InChIKey
FGXWKSZFVQUSTL-UHFFFAOYSA-N
Molecular formula
C22H24ClN5O2
Average molar mass
425.9 g/mol
Monoisotopic mass
425.16185269

Overview

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.

Names & identifiers

Preferred name
Domperidone
IUPAC
6-chloro-3-[1-[3-(2-oxo-3H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1H-benzimidazol-2-one
English name
Domperidone
Molecular formula
C22H24ClN5O2
Molecular weight
425.91

Names & synonyms

domperidone57808-66-9MotiliumDomperidonaDomperidonumR 33,812R-33812NSC299589NSC-299589DTXSID1045116KW 5338NSC-759575
Show more names
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-

Database identifiers

CAS
57808-66-9

Properties

Computed structural properties

XLogP
3.9
Topological polar surface area
67.9 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
30
Formal charge
0
Complexity
655

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP · 2 items

2.4

3.45

Solubility · 2 items

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 items

7.9

7.9

Collision Cross Section · 2 items

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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

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.

Hazard information

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%)

Toxicology

Drug Induced Liver Injury · 4 items

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

Safety data

wgk
3
rtecs
DE2275900
hs_code
29333990
risk_code
62-63
Signal word
Warning
Symbol(GHS)

Chemistry & industry

Pharmacology

ATC Code · 4 items

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 item

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 item

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 items

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.

Related reactions

32 records
New reaction record
HRID 46877 reaction equation
HRID 46877As productuspto-grants-1979_11
HRID 46881 reaction equation
HRID 46881As reactantuspto-grants-1979_11
HRID 46884 reaction equation
HRID 46884As reactantuspto-grants-1979_11
HRID 46885 reaction equation
HRID 46885As reactantuspto-grants-1979_11
HRID 46917 reaction equation
HRID 46917As reactantuspto-grants-1979_11
HRID 971757 reaction equation
HRID 971757As productuspto-grants-1979_07
HRID 971761 reaction equation
HRID 971761As reactantuspto-grants-1979_07
HRID 971763 reaction equation
HRID 971763As reactantuspto-grants-1979_07
Page 1 of 4

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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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]

Physicochemical properties

Melting point
240 · 240-244°C
Density
1.2904 · 1.2904 (rough estimate)
refractive index
1.54 · 1.5400 (estimate)
storage temp.
Store at RT
solubility
10 mg/mL · DMSO: >10 mg/mL
form
solid
pka
7.9 · pKa 7.90 (Uncertain)
color
white
Water Solubility
Slightly soluble in water.
Merck
14 · 14,3418
Stability
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 DataBase Reference
57808 · 57808-66-9(CAS DataBase Reference)
FDA UNII
5587267 Z69 · 5587267Z69
ATC code
3 FA03 · A03FA03
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Excreted unchanged in urine
1 % · <1%
Symbol(GHS)
8 · GHS08
Signal word
Warning
Hazard statements
361 fd · H361fd
Precautionary statements
201 · P201-P202-P280-P308+P313-P405-P501
Hazard Codes
Xn
Risk Statements
62 · 62-63
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
2275900 · DE2275900
HS Code
29333990 · 29333990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 · Repr. 2
GHS08
hazard_code
Xn
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H361fd
Hazard Classifications
Repr. 2
Precautionary statements
P201-P202-P280-P308+P313-P405-P501
Cellular LocationsMembrane

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Applications · 4 items

UsesIt is a kind of potent peripheral dopamine receptor antagonist with anti-vomiting and gastro-kinetic effects. It can affect the gastrointestinal motility to make the motility and tension of upper gastrointestinal tract return to normal and promote gastric emptying, enhancing the antral and duodenal motility, and coordinating the pyloric contraction. It can be used for the treatment of dyspepsia, and the nausea and vomiting induced by functional, organic, infection, dietary, radiation therapy or drug therapy. Because it almost has no inhibitory effect on dopamine receptor, there are no psychiatric and neurological side effects. And it can be used for treating the nausea caused by treating the Parkinson’s disease through taking dopamine agonists. It can be used as anticholinergic antispasmodics. Domperidone is a kind of phenyl imidazole compounds with a strong role in promoting gastric motility and antiemetic effect. It can strengthen the tension of the sphincter of the lower part of the esophagus, preventing the stomach-esophageal reflux, enhancing the gastric motility, promoting the gastric emptying, coordinating the stomach and duodenal motility, suppressing nausea, vomiting, and effectively preventing the bile reflux without affecting the secretion of gastric juice. This product is a kind of peripheral dopamine receptor antagonists which can directly block the gastrointestinal dopamine receptors and exhibit the stimulating effect of gastric motility. It can enhance the esophageal peristalsis and the tension of esophageal sphincter. Because of its poor penetration through the blood brain barrier, it has almost no antagonism against the dopamine receptor of the brain, and therefore can excluding the side effects of the spirit and the central nervous system.

UsesCOX2 inhibitor, antiinflammatory, antiarthritic

UsesA 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.

UsesFor management of dyspepsia, heartburn, epigastric pain, nausea, and vomiting.

Upstream & downstream products

Upstream raw materials

Silica gelBenzimidazole1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl esterN,N-DimethylformamidePotassium iodide2-NitrochlorobenzeneHydroxypropylChloroform4-Aminocyclohexanecarboxylic acid4-Methyl-2-pentanonePOTASSIUM CYANIDE5-Chloro-1,3-benzodioxole
Additional notes · 1 item

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.