4-{[7-bromo-5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]oxy}-4-oxobutanoic acid

• ChemBase ID: 179808
• Molecular Formular: C19H14BrClN2O5
• Molecular Mass: 465.68186
• Monoisotopic Mass: 463.97746124
• SMILES: C1(=NC(C(=O)Nc2c1cc(cc2)Br)OC(=O)CCC(=O)O)c1c(Cl)cccc1
• Canonical SMILES: O=C(OC1N=C(c2c(NC1=O)ccc(c2)Br)c1ccccc1Cl)CCC(=O)O
• InChI: InChI=1S/C19H14BrClN2O5/c20-10-5-6-14-12(9-10)17(11-3-1-2-4-13(11)21)23-19(18(27)22-14)28-16(26)8-7-15(24)25/h1-6,9,19H,7-8H2,(H,22,27)(H,24,25)
• InChIKey: NQTRBZXDWMDXAQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[7-bromo-5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]oxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{[7-bromo-5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]oxy}-4-oxobutanoic acid
• Synonyms: Cinazepam

Database IDs

• PubChem SID: 164235718
• PubChem CID: 629281

CALCULATED PROPERTIES

• Acid pKa: 3.3267143
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.8005462
• LogD (pH = 7.4): 0.5376724
• Log P: 3.9580216
• Molar Refractivity: 105.562 cm^3
• Polarizability: 40.15702 Å^3
• Polar Surface Area: 105.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Benzodiazepine receptor agonist

Product Information

• Application(s): Psychosedative; Sedative; Tranquilizer

REFERENCES

• S. A. Andronati, S. Yu. Makan, D. P. Neshchadin, L. N. Yakubovskaya, V. M. Sava and K. S. Andronati Bioaccessibility of cinazepam introduced as inclusion complex with beta-cyclodextrin. (Russ.).
• Khim.Farm.Zh. (32, No. 10, 3-5, 1998)