Basic information
- 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- PubChem CID
- 3151
- DTXSID
DTXSID1045116- ChEMBL
CHEMBL219916- ChEBI
CHEBI:31515- UNII
- 5587267Z69
- EC Number
- 260-968-7
- Nikkaji
- J3.199B
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
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]
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
Safety & regulation
GHS classification
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.
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
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)
- 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
Chemistry & industry
Pharmacology
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
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >500
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Applications
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
Suppliers50 total
北京华美互利生物化工010-56205725 · [email protected]
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Additional notes
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.
Related reactions
32 records
Linked notes
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