(2R,3R,4R,5S,6R)-6-{[7-chloro-5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172393
• Molecular Formular: C21H18Cl2N2O8
• Molecular Mass: 497.28222
• Monoisotopic Mass: 496.04402091
• SMILES: c1cc(cc2c1NC(=O)C(N=C2c1ccccc1Cl)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)Cl
• Canonical SMILES: Clc1ccc2c(c1)C(=NC(C(=O)N2)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)c1ccccc1Cl
• InChI: InChI=1S/C21H18Cl2N2O8/c22-8-5-6-12-10(7-8)13(9-3-1-2-4-11(9)23)25-19(18(29)24-12)33-21-16(28)14(26)15(27)17(32-21)20(30)31/h1-7,14-17,19,21,26-28H,(H,24,29)(H,30,31)/t14-,15-,16+,17-,19?,21-/m1/s1
• InChIKey: IWOJSSFCRQKNKN-PBXWZENZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{[7-chloro-5-(2-chlorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{[7-chloro-5-(2-chlorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepin-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 7-Chloro-5-(2-chlorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl β-D-Glucopyranosiduronic Acid; Lorazepam Glucuronide; Lorazepam β-D-Glucuronide, Mixture of Diastereomers. DISCONTINUED See L469865 Alternative Product

Database IDs

• CAS Number: 32781-79-6
• PubChem SID: 164228303
• PubChem CID: 71749839

CALCULATED PROPERTIES

• Acid pKa: 2.8558145
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.5152418
• LogD (pH = 7.4): -1.4126904
• Log P: 2.0767643
• Molar Refractivity: 114.9799 cm^3
• Polarizability: 44.765125 Å^3
• Polar Surface Area: 157.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L469860

A metabolite of Lorazepam.

REFERENCES

• ,,8) Greenblatt, D; J Pharmac Sci 1979, 68, 57,,,11) Greenblatt, D; Clin Pharmacol Ther 1988, 44, 326,,,2) Barr, J; Anesthesiology 2001, 95, 286,,,1) Blin, O; Clin Neuropharmacol 2001, 24, 71,,,