(2Z)-but-2-enedioic acid; 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: 122525
• Molecular Formular: C26H28ClN5O6
• Molecular Mass: 541.98342
• Monoisotopic Mass: 541.17281132
• SMILES: c1(=O)n(c2c([nH]1)cc(cc2)Cl)C1CCN(CC1)CCCn1c(=O)[nH]c2c1cccc2.C(=O)(/C=C\C(=O)O)O
• Canonical SMILES: Clc1ccc2c(c1)[nH]c(=O)n2C1CCN(CC1)CCCn1c(=O)[nH]c2c1cccc2.OC(=O)/C=C\C(=O)O
• InChI: InChI=1S/C22H24ClN5O2.C4H4O4/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;5-3(6)1-2-4(7)8/h1-2,4-7,14,16H,3,8-13H2,(H,24,29)(H,25,30);1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: OAUUYDZHCOULIO-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; 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: (2Z)-but-2-enedioic acid; 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; maleic acid; motilium
• Synonyms: Domperidone Maleate; 5-chloro-1-(1-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one maleate

Database IDs

• CAS Number: 57808-66-9
• PubChem SID: 162216878
• PubChem CID: 6604595

CALCULATED PROPERTIES

• 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: 7
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Antidopaminergic; Dopamine D2 antagonist

Product Information

• Salt Data: Maleate
• Application(s): Antiemetic drug

REFERENCES

• Ger. Pat., 1977, 2 632 870; CA, 87, 23274c, (synth, pharmacol)
• Brogden, R.N. et al., Drugs, 1982, 24, 360, (rev, pharmacol)
• Emanuel, M.B. et al., Clin. Res. Rev., 1983, 3, 15; 57; 91, (revs)
• Kennis, L.E.J. et al., Drug Dev. Res., 1986, 8, 133, (synth, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 882
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8895
• Prakash, A. et al., Drugs, 1998, 56, 429-445, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DYB875