1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-(1-hydroxyethyl)-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 170961
• Molecular Formular: C25H32ClN5O3
• Molecular Mass: 486.00628
• Monoisotopic Mass: 485.21936759
• SMILES: C1N(CCN(C1)c1cc(ccc1)Cl)CCCn1nc(n(c1=O)CCOc1ccccc1)C(O)C
• Canonical SMILES: Clc1cccc(c1)N1CCN(CC1)CCCn1nc(n(c1=O)CCOc1ccccc1)C(O)C
• InChI: InChI=1S/C25H32ClN5O3/c1-20(32)24-27-31(25(33)30(24)17-18-34-23-9-3-2-4-10-23)12-6-11-28-13-15-29(16-14-28)22-8-5-7-21(26)19-22/h2-5,7-10,19-20,32H,6,11-18H2,1H3
• InChIKey: VKGQYGXMUUBRBD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-(1-hydroxyethyl)-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-5-(1-hydroxyethyl)-4-(2-phenoxyethyl)-1,2,4-triazol-3-one
• Synonyms: 2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-2,4-dihydro-5-(1-hydroxyethyl)-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one Dihydrochloride; OH-NEF Dihydrochloride; Hydroxy Nefazodone Dihydrochloride

Database IDs

• CAS Number: 98159-83-2
• PubChem SID: 164226871
• PubChem CID: 11755137

CALCULATED PROPERTIES

• Acid pKa: 14.009494
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.1101027
• LogD (pH = 7.4): 3.5315351
• Log P: 3.7039483
• Molar Refractivity: 133.9452 cm^3
• Polarizability: 51.322372 Å^3
• Polar Surface Area: 71.85 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 155-160°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H948570

A metabolite of Nefazodone (N389100), an antidepressant.

REFERENCES

• Barbhaiya, R., et al.: Eur. J. Clin. Pharmacol., 49, 221 (1995)
• Greene, D., et al.: Clin. Pharmacokinet., 33, 260 (1995)
• Kalgutkar, A., et al.: Drug Metab. Dispos., 33, 243 (1995)