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Details

Stereochemistry ACHIRAL
Molecular Formula C25H32ClN5O2
Molecular Weight 470.007
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEFAZODONE

SMILES

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

InChI

InChIKey=VRBKIVRKKCLPHA-UHFFFAOYSA-N
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

HIDE SMILES / InChI

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

AUC

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

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
100 mg 2 times / day steady-state, oral
NEFAZODONE plasma
Homo sapiens
5.2 h
200 mg single, oral
NEFAZODONE plasma
Homo sapiens
5.7 h
100 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
59H4FCV1TF
Record Status Validated (UNII)
Record Version