U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C25H32ClN5O2.ClH
Molecular Weight 506.468
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEFAZODONE HYDROCHLORIDE

SMILES

Cl.CCC1=NN(CCCN2CCN(CC2)C3=CC=CC(Cl)=C3)C(=O)N1CCOC4=CC=CC=C4

InChI

InChIKey=DYCKFEBIOUQECE-UHFFFAOYSA-N
InChI=1S/C25H32ClN5O2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C25H32ClN5O2
Molecular Weight 470.007
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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. Within the serotonergic system, nefazodone acts as an antagonist at type 2 serotonin (5-HT2) post-synaptic receptors and, like fluoxetine-type antidepressants, inhibits pre-synaptic serotonin (5-HT) reuptake. These mechanisms increase the amount of serotonin available to interact with 5-HT receptors. Within the noradrenergic system, nefazodone inhibits norepinephrine uptake minimally. Nefazodone also antagonizes alpha(1)-adrenergic receptors, producing sedation, muscle relaxation, and a variety of cardiovascular effects. Nefazodone's affinity for benzodiazepine, cholinergic, dopaminergic, histaminic, and beta or alpha(2)-adrenergic receptors is not significant.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.8 nM [Ki]
290.0 nM [Ki]
5.5 nM [Ki]
84.0 nM [Ki]
52.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NEFAZODONE HYDROCHLORIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
880 μg/L
100 mg 2 times / day steady-state, oral
NEFAZODONE plasma
Homo sapiens
276 μg/L
100 mg single, oral
NEFAZODONE plasma
Homo sapiens
415 ng/mL
200 mg single, oral
NEFAZODONE plasma
Homo sapiens
1588 ng/mL
200 mg 2 times / day steady-state, oral
NEFAZODONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3213 μg × h/L
100 mg 2 times / day steady-state, oral
NEFAZODONE plasma
Homo sapiens
787 μg × h/L
100 mg single, oral
NEFAZODONE plasma
Homo sapiens
1220 ng × h/mL
200 mg single, oral
NEFAZODONE plasma
Homo sapiens
6378 ng × h/mL
200 mg 2 times / day steady-state, oral
NEFAZODONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
100 mg 2 times / day steady-state, oral
NEFAZODONE plasma
Homo sapiens
5.7 h
100 mg single, oral
NEFAZODONE plasma
Homo sapiens
5.2 h
200 mg single, oral
NEFAZODONE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Initial dose: 200 mg orally per day in two divided doses Maintenance dose: 300 to 600 mg orally per day
Route of Administration: Oral
In Vitro Use Guide
In vitro biliary excretion of micafungin in humans and rats was reduced by 75% in the presence of the bile salt export pump (BSEP) inhibitor nefazodone (25 uM)
Substance Class Chemical
Record UNII
27X63J94GR
Record Status Validated (UNII)
Record Version