(2S)-2,6-diamino-N-(3-{2-[(2H5)benzoyl]-4-chlorophenyl}-2-oxobutyl)hexanamide

• ChemBase ID: 160899
• Molecular Formular: C23H28ClN3O3
• Molecular Mass: 429.93972
• Monoisotopic Mass: 429.18191945
• SMILES: c1cc(cc(c1C(C(=O)CNC(=O)[C@H](CCCCN)N)C)C(=O)c1ccccc1)Cl
• Canonical SMILES: NCCCC[C@@H](C(=O)NCC(=O)C(c1ccc(cc1C(=O)c1ccccc1)Cl)C)N
• InChI: InChI=1S/C23H28ClN3O3/c1-15(21(28)14-27-23(30)20(26)9-5-6-12-25)18-11-10-17(24)13-19(18)22(29)16-7-3-2-4-8-16/h2-4,7-8,10-11,13,15,20H,5-6,9,12,14,25-26H2,1H3,(H,27,30)/t15?,20-/m0/s1
• InChIKey: WQRZTXVDPVPVDN-MBABXSBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,6-diamino-N-(3-{2-[(^2H₅)benzoyl]-4-chlorophenyl}-2-oxobutyl)hexanamide
• IUPAC Traditional name: (2S)-2,6-diamino-N-{3-[2-(^2H₅)benzoyl-4-chlorophenyl]-2-oxobutyl}hexanamide
• Synonyms: L-Lysyl-N-(2-benzoyl-4-chlorophenyl)-N-methyl-glycinamide-d5 Dihydrobromide; Prodiazepam-d5 Dihydrobromide; Ro 03-7355/000-d5 Dihydrobromide; Avizafone-d5 Dihydrobromide

Database IDs

• PubChem SID: 162255034
• PubChem CID: 71313533

CALCULATED PROPERTIES

• Acid pKa: 12.305635
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.4840782
• LogD (pH = 7.4): -0.24134475
• Log P: 2.9544542
• Molar Refractivity: 118.8408 cm^3
• Polarizability: 46.61221 Å^3
• Polar Surface Area: 115.28 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A794687

Prodrug of Diazepam (D416855), mainly used as an antidote to organophosphate poisoning.

REFERENCES

• Clair, P., et al.: Eur. J. Pharm. Sci., 9, 259 (2000)
• Breton, D., et al.: J. Pharm. Biomed. Anal., 41, 1274 (2000)
• Wetherell, J., et al.: Toxicol., 233, 120 (2000)