7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate

• ChemBase ID: 130335
• Molecular Formular: C15H11ClN2O2
• Molecular Mass: 286.71304
• Monoisotopic Mass: 286.05090528
• SMILES: Clc1cc2c(NC(=O)C[N+](=C2c2ccccc2)[O-])cc1
• Canonical SMILES: O=C1C[N+](=C(c2c(N1)ccc(c2)Cl)c1ccccc1)[O-]
• InChI: InChI=1S/C15H11ClN2O2/c16-11-6-7-13-12(8-11)15(10-4-2-1-3-5-10)18(20)9-14(19)17-13/h1-8H,9H2,(H,17,19)
• InChIKey: GGRWZBVSUZZMKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate
• IUPAC Traditional name: 7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate; demoxepam
• Synonyms: Nordazepam oxide; Demoxepam; Demoxepam; 7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide5-Phenyl-7-chloro-3H-1,4-benzodiazepin-2(1H)-one 4-oxide; 7-Chloro-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one 4-oxide; Chlordiazepoxide lactam; NSC 169898; NSC 46007; NSC 46077; Ro 5-2092

Database IDs

• CAS Number: 963-39-3
• PubChem SID: 162224614
• PubChem CID: 13756
• Chemspider ID: 10441314
• KEGG ID: D02600
• Unique Ingredient Identifier: 8X1XP5M0SB
• Wikipedia Title: Demoxepam

CALCULATED PROPERTIES

• Acid pKa: 12.189041
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.8952608
• LogD (pH = 7.4): 2.8952541
• Log P: 2.8952608
• Molar Refractivity: 80.1531 cm^3
• Polarizability: 29.050224 Å^3
• Polar Surface Area: 57.85 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Half Life: 35 to 40 h
• Mechanism of Action: Benzodiazepine receptor agonist

Product Information

• Application(s): Psychosedative; Tranquilliser

DETAILS

Toronto Research Chemicals - D231395

A major metabolite of Chlordiazepoxide (C327050). A benzodiapine derivative with anticonvulsant properties.

REFERENCES

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• Sadee, W., Arch. Pharm. (Weinheim, Ger.), 1969, 302, 769, (pmr)
• Schwartz, M.A. et al., J. Pharm. Sci., 1970, 59, 1569; 1971, 60, 438, (metab)
• Vane, F., Arch. Mass Spectral Data, 1971, 2, 712, (ms)
• Robichaud, R.C. et al., Arch. Int. Pharmacodyn. Ther., 1974, 211, 165, (pharmacol)
• Walser, A. et al., J. Het. Chem., 1974, 11, 619, (synth)
• Levillain, P. et al., Eur. J. Med. Chem. (Chim. Ther.), 1975, 10, 433, (uv)
• Kovar, K.A. et al., Arch. Pharm. (Weinheim, Ger.), 1983, 316, 834, (cmr)