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

• ChemBase ID: 1020
• Molecular Formular: C25H32ClN5O2
• Molecular Mass: 470.00688
• Monoisotopic Mass: 469.22445297
• SMILES: Clc1cc(N2CCN(CC2)CCCn2nc(n(c2=O)CCOc2ccccc2)CC)ccc1
• Canonical SMILES: CCc1nn(c(=O)n1CCOc1ccccc1)CCCN1CCN(CC1)c1cccc(c1)Cl
• InChI: InChI=1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3
• InChIKey: VRBKIVRKKCLPHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-ethyl-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: nefazodone
• Brand Name: Dutonin; Serzone
• Synonyms: Nefazodona [Spanish]; Nefazodone Hcl; Nefazodone Hydrochloride; Nefazodonum [Latin]; Nefazodone

Database IDs

• CAS Number: 83366-66-9
• PubChem SID: 160964483; 46508323
• PubChem CID: 4449
• CHEBI ID: 7494
• ATC CODE: N06AX06
• CHEMBL: 623
• Chemspider ID: 4294
• DrugBank ID: DB01149
• KEGG ID: D08257
• Unique Ingredient Identifier: 59H4FCV1TF
• Wikipedia Title: Nefazodone
• Medline Plus: a695005

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.0591223
• LogD (pH = 7.4): 4.4805546
• Log P: 4.652968
• Molar Refractivity: 132.376 cm^3
• Polarizability: 50.688282 Å^3
• Polar Surface Area: 51.62 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.71
• LOG S: -3.83
• Solubility (Water): 6.98e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.7

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 20% (variable)
• Excretion: Urine (55%), Feces (20–30%)
• Half Life: 2–4 hours
• Metabolism: Hepatic (active metabolites, including mCPP)
• Protein Bound: >99%
• Legal Status: Rx-only
• Pregnancy Category: C

DETAILS

DrugBank - DB01149

• Drug Groups: approved; withdrawn
• Description: Nefazodone hydrochloride (trade name Serzone) is an antidepressant drug marketed by Bristol-Myers Squibb. Its sale was discontinued in 2003 in some countries, due to the small possibility of hepatic (liver) injury, which could lead to the need for a liver transplant, or even death. The incidence of severe liver damage is approximately 1 in 250,000 to 300,000 patient-years. On May 20, 2004, Bristol-Myers Squibb discontinued the sale of Serzone in the United States. [Wikipedia]
• Indication: For the treatment of depression.
• Pharmacology: Nefazodone, an antidepressant synthetically derived phenylpiperazine, is used to treat major depression. Although it is structurally similar to trazodone, nefazodone has a mechanism of action different from other antidepressants and, hence, lacks the risk for major cardiovascular toxicity seen with tricyclics and insomnia and inhibition of REM sleep seen with the selective serotonin reuptake inhibitors.
• Toxicity: Cases of life-threatening hepatic failure have been reported in patients treated; with nefazodone.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Nefazodone is rapidly and completely absorbed. Its absolute bioavailability is low (about 20%).
• Half Life: 2-4 hours
• Protein Binding: Greater than 99% (in vitro, human plasma proteins).
• Elimination: Nefazodone is extensively metabolized after oral administration by n-dealkylation and aliphatic and aromatic hydroxylation, and less than 1% of administered nefazodone is excreted unchanged in urine.
• Distribution: * 0.22 to 0.87 L/kg
• References: Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. Pubmed