1-[(3Z)-4-(4-methylpiperazin-1-yl)-2-sulfanylidene-2,3-dihydro-1H-1,5-benzodiazepin-3-ylidene]propan-2-one

• ChemBase ID: 175627
• Molecular Formular: C17H20N4OS
• Molecular Mass: 328.4319
• Monoisotopic Mass: 328.13578228
• SMILES: c12c([nH]c(=S)/c(=C\C(=O)C)/c(n1)N1CCN(CC1)C)cccc2
• Canonical SMILES: CN1CCN(CC1)c1nc2ccccc2[nH]c(=S)/c/1=C\C(=O)C
• InChI: InChI=1S/C17H20N4OS/c1-12(22)11-13-16(21-9-7-20(2)8-10-21)18-14-5-3-4-6-15(14)19-17(13)23/h3-6,11H,7-10H2,1-2H3,(H,19,23)/b13-11-
• InChIKey: UZXKASHICBLMCC-QBFSEMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3Z)-4-(4-methylpiperazin-1-yl)-2-sulfanylidene-2,3-dihydro-1H-1,5-benzodiazepin-3-ylidene]propan-2-one
• IUPAC Traditional name: 1-[(3Z)-2-(4-methylpiperazin-1-yl)-4-sulfanylidene-5H-1,5-benzodiazepin-3-ylidene]propan-2-one
• Synonyms: (1Z)-1-[4,5-Dihydro-2-(4-methyl-1-piperazinyl)-4-thioxo-3H-1,5-benzodiazepin-3-ylidene]-2-propanone; Olanzapine Thiolactam Impurity

Database IDs

• CAS Number: 1017241-36-9
• PubChem SID: 164231537
• PubChem CID: 71751201

CALCULATED PROPERTIES

• Acid pKa: 8.201308
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.63303006
• LogD (pH = 7.4): 1.7717403
• Log P: 1.6983105
• Molar Refractivity: 101.2519 cm^3
• Polarizability: 36.902374 Å^3
• Polar Surface Area: 47.94 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow to Brownish Yellow Solid
• Melting Point: 152-156°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - O253780

A degradation product of Olanzapine (LY170053) (O253750) in solid oral formulations.

REFERENCES

• Chakrabarti, J., et al.: J.Med. Chem., 25, 1133 (1982)
• Chafetz, L., et al.: J. Pharm. Sci., 73, 1186 (1982)
• Hartauer, K., et al.: Pharm. Dev. Technol., 5, 303 (1982)