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

• ChemBase ID: 1055
• Molecular Formular: C22H24ClN5O2
• Molecular Mass: 425.91126
• Monoisotopic Mass: 425.16185271
• SMILES: Clc1cc2[nH]c(=O)n(C3CCN(CC3)CCCn3c4c([nH]c3=O)cccc4)c2cc1
• Canonical SMILES: Clc1ccc2c(c1)[nH]c(=O)n2C1CCN(CC1)CCCn1c(=O)[nH]c2c1cccc2
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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
• IUPAC Traditional name: motilium
• Brand Name: Motilium; Nauzelin; Lopac-D-122
• Synonyms: Domperidone; Motilium; Motillium; Motinorm; Costi; 5-Chloro-1-[1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one; 4-(5-Chloro-2-oxo-1-benzimidazolinyl)-1-[3-(2-oxobenzimidazolinyl)propyl]piperidine; Domperidone

Database IDs

• CAS Number: 57808-66-9
• EC Number: 260-968-7
• MDL Number: MFCD00069256
• PubChem SID: 160964518; 46508314; 24277911
• PubChem CID: 3151
• CHEBI ID: 31515
• ATC CODE: A03FA03; QP51AX24
• CHEMBL: 219916
• Chemspider ID: 3039
• DrugBank ID: DB01184
• IUPHAR ligand ID: 965
• KEGG ID: D01745
• Unique Ingredient Identifier: 5587267Z69
• Wikipedia Title: Domperidone

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.524702
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3633938
• LogD (pH = 7.4): 2.746269
• Log P: 2.900103
• Molar Refractivity: 119.3737 cm^3
• Polarizability: 44.200592 Å^3
• Polar Surface Area: 67.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.7
• LOG S: -3.66
• Solubility (Water): 9.25e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble; 0.1 M NaOH: slightly soluble; 0.986 mg/L; DMSO: >10 mg/mL; H2O: insoluble
• Apperance: white powder
• Hydrophobicity(logP): 2.4

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: DE2275900
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: II
• Australian Hazchem: 2XE
• Risk Statements: 63-62; R:25
• Safety Statements: 26-36; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Admin Routes: Oral, intravenous, rectal
• Bioavailability: High
• Excretion: Breast milk, renal
• Half Life: 7 hours
• Metabolism: Hepatic and intestinal (first-pass)
• Protein Bound: 91–93%
• Legal Status: Not approved for use or sale: US; prescription medicine (POM): India, Australia, Canada, Israel; Over the Counter (OTC): UK (Pharmacy only), Belgium, Egypt, Ireland, Italy, Japan, Netherlands, South Africa, Switzerland, China, Russia, Slovakia, Thailand, Malta, South Korea, and Romania
• Pregnancy Category: Not classified (US)
• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816), KCNH2(3757)rat ... Drd1a(24316), Drd2(24318), Drd3(29238), Htr3a(79246)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base

DETAILS

DrugBank - DB01184

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: For management of dyspepsia, heartburn, epigastric pain, nausea, and vomiting.
• Pharmacology: 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.
• Toxicity: Side effects include galactorrhea, gynecomastia, or menstrual irregularities.
• Affected Organisms: Humans and other mammals
• Absorption: Fast
• Half Life: 7 hours
• Protein Binding: 91%-93%
• References: Silvers D, Kipnes M, Broadstone V, Patterson D, Quigley EM, McCallum R, Leidy NK, Farup C, Liu Y, Joslyn A: Domperidone in the management of symptoms of diabetic gastroparesis: efficacy, tolerability, and quality-of-life outcomes in a multicenter controlled trial. DOM-USA-5 Study Group. Clin Ther. 1998 May-Jun;20(3):438-53. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S2461

Research Area: Metabolic Disease
Biological Activity:
Domperidone(Motilium) is a dopamine blocker and an antidopaminergic reagent. It blocks the action of. 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 (area postrema on the floor of the fourth ventricle and rhomboid fossa). [1]References on Domperidone (Motilium)[1] http://en.wikipedia.org/wiki/Domperidone, ,

Sigma Aldrich - D122

Biochem/physiol Actions
Peripheral dopamine receptor antagonist that does not cross the blood-brain barrier; anti-emetic.

REFERENCES

• Silvers D, Kipnes M, Broadstone V, Patterson D, Quigley EM, McCallum R, Leidy NK, Farup C, Liu Y, Joslyn A: Domperidone in the management of symptoms of diabetic gastroparesis: efficacy, tolerability, and quality-of-life outcomes in a multicenter controlled trial. DOM-USA-5 Study Group. Clin Ther. 1998 May-Jun;20(3):438-53. Pubmed
• http://en.wikipedia.org/wiki/Domperidone