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HomeProduct name listDomperidone

Domperidone

Synonym(s):4-(5-Chloro-2-oxo-1-benzimidazolinyl)-1-[3-(2-oxobenzimidazolinyl)propyl]piperidine

  • CAS NO.:57808-66-9
  • Empirical Formula: C22H24ClN5O2
  • Molecular Weight: 425.91
  • MDL number: MFCD00069256
  • EINECS: 260-968-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 19:05:58
Domperidone Structural

What is Domperidone?

Toxicity

Side effects include galactorrhea, gynecomastia, or menstrual irregularities.

Chemical properties

White or almost white powder.

Originator

Motilium,Cilag,Switz.,1979

The Uses of Domperidone

Domperidone is a medication that enhances peristalsis or contractions of the stomach and intestines. Domperidone is also used to treat nausea and vomiting caused by other medicines used to treat Parkinson's disease.

The Uses of Domperidone

COX2 inhibitor, antiinflammatory, antiarthritic

The Uses of Domperidone

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

Background

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.

Indications

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

What are the applications of Application

Domperidone is a peripheral D2DR inhibitor

Definition

ChEBI: 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.

Manufacturing Process

A mixture of 2.3 parts of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2- one, 2.5 parts of 5-chloro-1,3-dihydro-l-(4-piperidinyl)-2H-benzimidazol-2- one, 3.2 parts of sodium carbonate, 0.1 part of potassium iodide and 80 parts of 4-methyl-2-pentanone is stirred and refluxed for 24 hours. The reaction mixture is cooled to room temperature and water is added. The undissolved product is filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and 10% methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and recrystallized from a mixture of N,N-dimethylformamide and water, yielding 1.3 parts (30%) of 5- chloro-1-[1-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl]-4- piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one; MP 242.5°C.

Side Effects

Common side effects of Domperidone include: headache, dry mouth, diarrhoea or abdominal cramps. They are usually mild and go away on their own. Serious adverse reactions include: seizures or cramps, fast or irregular heartbeat, itching, lumpy rash (hives), or severe allergic reactions.

brand name

Motilium (Janssen);Evixub;Kw 5338;Moperidona;Neta662;R 33812;Tametil;Touristic.

Therapeutic Function

Antiemetic

World Health Organization (WHO)

Domperidone, a peripheral dopaminergic antagonist, was introduced in 1979 for the symptomatic relief of acute nausea and vomiting. The major manufacturer became aware that the injectable formulation was being used in some countries in much higher doses than those recommended to combat nausea and vomiting in cancer patients treated with cytostatic agents. Such use - which was not in conformity with the approved indications - was associated with cardiotoxicity, which in some cases was fatal, and the manufacturer decided to withdraw the injectable dosage form from the market worldwide in January 1985. Suppositories, tablets and a suspension remain available and the manufacturer continues to supply the injection for the treatment of a named patient at the written request of a doctor on the understanding that the appropriate dosage recommendations will be followed.

Biological Activity

Peripheral dopamine D 2 -like receptor antagonist that does not readily cross the blood brain barrier. Displays gastroprokinetic and antiemetic properties; increases the frequency and duration of antral and duodenal contractions and protects from apomorphine-induced emesis (ED 50 values are 0.003 and 0.03 mg/kg for i.v. and oral administration respectively).

Pharmacokinetics

Domperidone 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.

Clinical Use

Acute nausea and vomiting (including that caused by levodopa and bromocriptine)
Gastro-oesophageal reflux
Dyspepsia

Veterinary Drugs and Treatments

Domperidone may be useful for treatment of fescue toxicosis in pregnant mares or as a prokinetic or antiemetic agent in small animals. It has more effect on conditions with delayed gastric emptying than other GI hypomotility conditions.
Via its effects on prolactin, domperidone may also be used to stimulate milk production in horses and small animals.
Domperidone has been shown to increase plasma ACTH in horses with equine pituitary pars intermedia dysfunction (Equine Cushing’s) and may be useful in helping diagnose this condition.

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: possible increased risk of ventricular arrhythmias with clarithromycin, delamanid and erythromycin - avoid with clarithromycin and erythromycin.
Antifungals: possibly increased risk of ventricular arrhythmias with itraconazole, ketoconazole and voriconazole - avoid.
Antimalarials: possible increased risk of ventricular arrhythmias with piperaquine with artenimol - avoid.
Antivirals: possible increased risk of ventricular arrhythmias with boceprevir; possible increased risk of ventricular arrhythmias with ritonavir, saquinavir and telaprevir - avoid
Apomorphine: possible increased risk of ventricular arrhythmias.
Cobicistat: possible increased risk of ventricular arrhythmias - avoid.
Cytotoxics: increased risk of ventricular arrhythmias with bosutinib and ceritinib - avoid with bosutinib.

Metabolism

Metabolism

Domperidone undergoes extensive first-pass hepatic and intestinal metabolism. It undergoes rapid and extensive hepatic metabolism. The main metabolic pathways are N-dealkylation by cytochrome P450 isoenzyme CYP3A4, and aromatic hydroxylation by CYP3A4, CYP1A2, and CYP2E1.
About 30% of an oral dose is excreted in urine within 24 hours, almost entirely as metabolites; the remainder of a dose is excreted in faeces over several days, about 10% as unchanged drug.

storage

Room temperature

Properties of Domperidone

Melting point: 240-244°C
Density  1.2904 (rough estimate)
refractive index  1.5400 (estimate)
storage temp.  Store at RT
solubility  DMSO: >10 mg/mL
form  solid
pka pKa 7.90 (Uncertain)
color  white
Water Solubility  Slightly soluble in water.
Merck  14,3418
Stability: Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference 57808-66-9(CAS DataBase Reference)

Safety information for Domperidone

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
Precautionary Statement Codes P201:Obtain special instructions before use.
P202:Do not handle until all safety precautions have been read and understood.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313:IF exposed or concerned: Get medical advice/attention.
P405:Store locked up.
P501:Dispose of contents/container to..…

Computed Descriptors for Domperidone

InChIKey FGXWKSZFVQUSTL-UHFFFAOYSA-N

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