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Domperidone

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Products Intro: Product Name:4-(5-Chloro-2-oxo-1-benzimidazolinyl)-1-[3-(2-oxobenzimidazolinyl)propyl]piperidine
CAS:57808-66-9
Purity:98% (Min,HPLC) Package:100g;1kg;5kg,10kg,25kg,50kg
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CAS:57808-66-9
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CAS:57808-66-9
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Products Intro: Product Name:Domperidone
CAS:57808-66-9
Purity:90%+ Package:10mg, 25mg, 50mg, 100mg, Other scale please email Sales@pipitech.com Remarks:5-Chloro-1-[1-[3-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)propyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

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  • Domperidone
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  • 2020-05-15
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  • Domperidone
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  • 2020-01-19
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Domperidone Basic information
Pharmacodynamics Side effects Gastro-kinetic drugs Chemical Properties Uses Production method
Product Name:Domperidone
Synonyms:kw-5338;midazol-1-yl)propyl)-4-piperidinyl)-;Domperidone,Motilium;5-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-one;5-Chloro-1-[1-[3-(2-oxo-1-benzimidazolyl)propyl]-4-piperidyl]benzimidazol-2-one;DoMperidone-d6;DoMperidone Sustained Release Pellets;DOMPERIDONE BASE
CAS:57808-66-9
MF:C22H24ClN5O2
MW:425.91
EINECS:260-968-7
Product Categories:VIOXX;Other APIs;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds;Dopamine receptor
Mol File:57808-66-9.mol
Domperidone Structure
Domperidone Chemical Properties
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
pkapKa 7.90 (Uncertain)
color white
Water Solubility Slightly soluble in water.
Merck 14,3418
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyFGXWKSZFVQUSTL-UHFFFAOYSA-N
CAS DataBase Reference57808-66-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 62-63
Safety Statements 26-36
WGK Germany 3
RTECS DE2275900
HS Code 29333990
MSDS Information
ProviderLanguage
Domperidone English
SigmaAldrich English
Domperidone Usage And Synthesis
Pharmacodynamics

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.

Side effects

Side effects associated with domperidone include dry mouth, abdominal cramps, diarrhea, nausea, rash, itching, hives, and hyperprolactinemia (the symptoms of which may include breast enlargement, galactorrhea, breast pain/tenderness, gynecomastia, hypogonadism, and menstrual irregularities).

Gastro-kinetic drugsDomperidone is a commonly used antiemetic and gastro-kinetic drug with its appearance being white to light yellow powder and bitter taste. It is almost insoluble in water, slightly soluble in ethanol, easily soluble in lactic acid as well as soluble in citrate. This product is a kind of peripheral dopamine receptor antagonists with strong action. Domperidone can block the DA1 and DA2 receptor next to the synapses, antagonizing the inhibitory effect of dopamine on the postsynaptic cholinergic neurons of myenteric plexus and causing the stomach contractions. It can promote the motility and tension of digestive tract motility to return to normal function, promoting the emptying of stomach, increasing the motility of gastric antral and duodenum, coordinating the contraction of the pylorus as well as enhancing the esophageal peristalsis and the tension of the lower esophageal sphincter. Because it has a poor penetration capability through the blood-brain barrier with almost no antagonism on the dopamine receptor, you can rule out the side effects of spirit and the central nervous system side. It has rapid absorption after oral administration with the plasma concentration reaching peak after 15~30 min. In addition to the central nervous system, it is also widely distributed in other parts of the body. Owing to the presence of "first pass" hepatic metabolism and intestinal metabolism, it has a low oral bioavailability. The half-life of this product is 7h with 30% excreted through the urine at 24 h after the oral administration and about 60% excreted through faeces within 4 days.
Indications
1, Digestion dysfunction symptoms caused by delayed gastric emptying, gastroesophageal reflux, chronic gastritis and esophagitis including nausea, vomiting, belching, abdominal fullness, abdominal pain, regurgitation caused burning sensation of mouth and stomach.
2, Parkinson's disease and nausea and vomiting caused by various kinds of reasons such as functional, infection, dietary, radiotherapy or drug therapy and dopamine receptor agonists (such as levodopa, bromocriptine) therapy.
3, it is suitable for treating migraine, dysmenorrhea, traumatic brain injury and intracranial lesions, radiation therapy and the nausea and vomiting caused by levodopa, nonsteroidal anti-inflammatory drug.
4, it is effective in treating the nausea and vomiting caused by various organic or functional gastrointestinal disorders in elderly people.
5, Domperidone is not effective in treating the vomiting caused by surgery or anesthesia and chemotherapy.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
Chemical PropertiesFrom dimethylformamide-water to obtain its white crystalline powder; the melting points is 242.5 ℃
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.
Production method2-nitro-1, 4-dichlorobenzene is reacted with 4-amino-cyclohexanecarboxylic acid ethyl ester and is further subject to hydrogenation reduction, urea cyclization, hydrolysis, to give 5-chloro-1-(piperidin-4-yl)-1,3-dihydro-benzimidazol-2-ketone.
Hydroxyl propylamine can have nucleophilic substitution of the chlorine of 2-nitro-chlorobenzene and then be subject to hydrogenation to reduce the nitro group to amino group; then have cyclization with potassium chloride and further chlorination to give 1-(3-chloropropyl)-2,3-dihydro-1H-benzimidazol-2-ketone.
The two benzimidazole derivative obtained above are processed as follows and can give domperidone. 2.3 parts of 1-(3-chloropropyl)-2,3-dihydro-1H-benzimidazol-2-ketone, 2.5 parts of 5--chloro-I-(piperidin-4-yl)-1,3-2H-dihydro-benzimidazol-2-one, 3.2 parts of sodium carbonate, 0.1 parts of potassium iodide and 80 parts of 4-methyl-2-pentanone were stirred and reflux for 24h. After being cooled to room temperature, add water, filter off the insolubles and purify it by silica gel column chromatography with the eluting solution being chloroform and 10% methanol mixture. The effluent containing the product were collected and concentrated. The residue was crystallized using 4-methyl-2-pentanone. After filtration, apply re-crystallization with the mixture of dimethylformamide and water to obtain 1.3 parts of domperidone with the yield being 30% and the mp being 242.5 ℃.
Chemical PropertiesWhite or almost white powder.
OriginatorMotilium,Cilag,Switz.,1979
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.
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.
Manufacturing ProcessA 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.
Brand nameMotilium (Janssen);Evixub;Kw 5338;Moperidona;Neta662;R 33812;Tametil;Touristic.
Therapeutic FunctionAntiemetic
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 ActivityPeripheral 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).
Veterinary Drugs and TreatmentsDomperidone 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.
Tag:Domperidone(57808-66-9) Related Product Information
5-CHLORO-1H-BENZOIMIDAZOL-2-OL 2,3-DIHYDRO-1H-BENZO[D]IMIDAZOLE METHYL-(3-PIPERIDIN-1-YL-PROPYL)-AMINE 3,3'-IMINOBIS(N,N-DIMETHYLPROPYLAMINE) N-(1-METHYLPIPERIDIN-4-YL)ANILINE 1-(2-PROPYL)-2-BENZIMIDAZOLIDINONE N N'-DIMETHYLDIPROPYLENETRIAMINE (ATOFI& DIPROPYLENETRIAMINE Domperidone Difluorochloromethane benzimidazolone Phenformin Domperidone Tablet Alkyl benzimidazole Benzimidazole Diphenoxylate Haloperidol DROPERIDOL