U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=CC(Cl)=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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/nefazodone.html

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

CNS Active
4002
Curator's Comment: antidepressant

Originator

Bristol-Myers Squibb
144
Curator's Comment: # Bristol-Myers Squibb

Approval Year

1994
152
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 5.8 nM [Ki]
Antagonist
2849
 290.0 nM [Ki]
Antagonist
2849
 5.5 nM [Ki]
Antagonist
2849
 84.0 nM [Ki]
Antagonist
2849
 52.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
NEFAZODONE HYDROCHLORIDE

Approved Use

Nefazodone hydrochloride tablets are indicated for the treatment of depression. When deciding among the alternative treatments available for this condition, the prescriber should consider the risk of hepatic failure associated with Nefazodone hydrochloride treatment. In many cases, this would lead to the conclusion that other drugs should be tried first.

Launch Date

2003
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
880 μg/L
REVIEW
https://link.springer.com/article/10.2165/00003088-199733040-00002
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
276 μg/L
REVIEW
https://link.springer.com/article/10.2165/00003088-199733040-00002
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
415 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8951188/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
1588 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8951188/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3213 μg × h/L
REVIEW
https://link.springer.com/article/10.2165/00003088-199733040-00002
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
787 μg × h/L
REVIEW
https://link.springer.com/article/10.2165/00003088-199733040-00002
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1220 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8951188/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
6378 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8951188/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
REVIEW
https://link.springer.com/article/10.2165/00003088-199733040-00002
100 mg 2 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.7 h
REVIEW
https://link.springer.com/article/10.2165/00003088-199733040-00002
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8951188/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NEFAZODONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Other AEs: Nausea and vomiting...
Other AEs:
Nausea and vomiting
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Other AEs: Nausea and vomiting...
Other AEs:
Nausea and vomiting
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
430 mg 1 times / day steady, oral
Highest studied dose
Dose: 430 mg, 1 times / day
Route: oral
Route: steady
Dose: 430 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
Other AEs: Headaches, Dry mouth...
Other AEs:
Headaches (53%)
Dry mouth (42%)
Diarrhea (42%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Other AEs: Somnolence...
Other AEs:
Somnolence (25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Other AEs: Dry mouth, Nausea...
Other AEs:
Dry mouth (25%)
Nausea (22%)
Dizziness (17%)
Constipation (14%)
Asthenia (11%)
Light headedness (10%)
Blurred vision (9%)
Confusion (7%)
Abnormal vision (7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Disc. AE: Nausea, Headache...
AEs leading to
discontinuation/dose reduction:
Nausea (3.5%)
Headache (2.9%)
Dizziness (1.9%)
Somnolence (1.5%)
Insomnia (1.5%)
Asthenia (1.3%)
Agitation (1.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
healthy, elderly
Health Status: healthy
Age Group: elderly
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Other AEs: Nausea and vomiting...
Other AEs:
Nausea and vomiting
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
healthy, younger
Health Status: healthy
Age Group: younger
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Other AEs: Nausea and vomiting...
Other AEs:
Nausea and vomiting
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
AEs

AEs

AESignificanceDosePopulation
Nausea and vomiting
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Nausea and vomiting
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Diarrhea 42%
430 mg 1 times / day steady, oral
Highest studied dose
Dose: 430 mg, 1 times / day
Route: oral
Route: steady
Dose: 430 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
Dry mouth 42%
430 mg 1 times / day steady, oral
Highest studied dose
Dose: 430 mg, 1 times / day
Route: oral
Route: steady
Dose: 430 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
Headaches 53%
430 mg 1 times / day steady, oral
Highest studied dose
Dose: 430 mg, 1 times / day
Route: oral
Route: steady
Dose: 430 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
Somnolence 25%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Light headedness 10%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Asthenia 11%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Constipation 14%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Dizziness 17%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Nausea 22%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Dry mouth 25%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Abnormal vision 7%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Confusion 7%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Blurred vision 9%
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Agitation 1.2%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Asthenia 1.3%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Insomnia 1.5%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Somnolence 1.5%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Dizziness 1.9%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Headache 2.9%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Nausea 3.5%
Disc. AE
600 mg 1 times / day steady, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: steady
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Nausea and vomiting
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
healthy, elderly
Health Status: healthy
Age Group: elderly
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Nausea and vomiting
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
healthy, younger
Health Status: healthy
Age Group: younger
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

substrate
1946
inhibitor
2507

substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

P-gp
1741

BSEP
550
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no
CYP2D6
2546
 weak
P-gp
1932
 yes [IC50 4.7 uM]
BSEP
554
 yes [IC50 9 uM]
CYP3A4
2633
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
CYP2D6
1388
 yes
mCPP
2
CYP3A4
1946
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7495
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7495
ChemicalBook
CB8144863
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8144863
eMolecules
592758
https://www.emolecules.com/cgi-bin/more?vid=592758
MolPort
MolPort-003-983-466
https://www.molport.com/shop/molecule-link/MolPort-003-983-466
PubMed

PubMed

TitleDatePubMed
Nefazodone decreases anxiety during marijuana withdrawal in humans.
2003-01
Enhanced resolution triple-quadrupole mass spectrometry for fast quantitative bioanalysis using liquid chromatography/tandem mass spectrometry: investigations of parameters that affect ruggedness.
2003
An open pilot study of nefazodone in depression with anger attacks: relationship between clinical response and receptor binding.
2002-12-30
Combination therapy in the treatment of major depressive disorder complicated by fibromyalgia and menopause.
2002-11-22
Nefazodone treatment of pathological gambling: a prospective open-label controlled trial.
2002-11
Effects of smoked marijuana in healthy and HIV + marijuana smokers.
2002-11
Nefazodone alters NPY immunostaining in rat arcuate-paraventricular projection without changes in food intake and body weight.
2002-10
Antidepressant-induced sexual dysfunction.
2002-10
Effects of nefazodone on voluntary ethanol consumption induced by isolation stress in young and aged rats.
2002-10
Nefazodone and cyp450 3a4 interactions with cyclosporine and tacrolimus1.
2002-09-15
[Pharmacological justification for the use of new antidepressant drugs].
2002-09
Reversible penile priapism associated with nefazodone.
2002-09
Rhabdomyolysis with simvastatin and nefazodone.
2002-09
An open-label clinical trial of nefazodone in hypochondriasis.
2002-08-22
Nefazodone and liver damage.
2002-08
Sexual function and satisfaction in the treatment of chronic major depression with nefazodone, psychotherapy, and their combination.
2002-08
Differential effects of amitriptyline, nefazodone and paroxetine on performance and brain indices of visual selective attention and working memory.
2002-08
[Acute liver failure in nefazodone therapy? A case report].
2002-07
Optimizing antidepressant treatment: efficacy and tolerability.
2002-06
Differential effects of nefazodone and cognitive behavioral analysis system of psychotherapy on insomnia associated with chronic forms of major depression.
2002-06
Randomised controlled study of sleep after nefazodone or paroxetine treatment in out-patients with depression.
2002-06
Nefazodone treatment of dysthymic disorder an open, long-term, prospective pilot study.
2002-05
Pharmacological interactions of statins.
2002-05
Symptomatic and syndromal anxiety in chronic forms of major depression: effect of nefazodone, cognitive behavioral analysis system of psychotherapy, and their combination.
2002-05
Hepatic adverse reactions associated with nefazodone.
2002-05
Loratadine/nefazodone interaction.
2002-05
Prevalence of sexual dysfunction among newer antidepressants.
2002-04
Serzone. Beware of dangerous liver problems.
2002-04
Induction of hyperlocomotion in mice exposed to a novel environment by inhibition of serotonin reuptake. A pharmacological characterization of diverse classes of antidepressant agents.
2002-04
Human CYP3A4 and the metabolism of nefazodone and hydroxynefazodone by human liver microsomes and heterologously expressed enzymes.
2002-04
Evaluating changes in sexual functioning in depressed patients: sensitivity to change of the CSFQ.
2002-03-16
From the Food and Drug Administration.
2002-03-06
New antidepressants in the treatment of neuropathic pain. A review.
2002-03
Hepatotoxicity associated with the new antidepressants.
2002-02
Does psychosocial functioning improve independent of depressive symptoms? A comparison of nefazodone, psychotherapy, and their combination.
2002-01-15
Nefazodone in the treatment of elderly patients with depressive disorders: a prospective, observational study.
2002
Clinically significant drug interactions with antidepressants in the elderly.
2002
Mood disorders in patients with epilepsy: epidemiology and management.
2002
Interaction potential of lercanidipine, a new vasoselective dihydropyridine calcium antagonist.
2002
Cost savings with nefazodone in treating depression.
2002
Antidepressant dosing and switching guidelines: focus on nefazodone.
2002
Six-year perspectives on the safety and tolerability of nefazodone.
2002
Overview of psychiatric disorders and the role of newer antidepressants.
2002
Clinical use of nefazodone in major depression: a 6-year perspective.
2002
Pharmacology of antidepressants: focus on nefazodone.
2002
Increased premenstrual dosing of nefazodone relieves premenstrual magnification of depression.
2002
Pharmacotherapy for post-traumatic stress disorder: a comprehensive review.
2001-10
An open-label, 12-week clinical and sleep EEG study of nefazodone in chronic combat-related posttraumatic stress disorder.
2001-10
Charleston Antidepressant Drug Interactions Surveillance Program (CADISP).
2001
Pharmacokinetically induced benzodiazepine withdrawal.
2001
Patents

Patents

20010014678
18
JP2002511409A
23
JP2002528505A
2
JP2006505569A
69
JP2007514770A
77
JP2007516170A
14
JP2011508748A
30
JP2011526251A
112
JPH09165337A
2

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
Created
by admin
on Mon Mar 31 18:29:35 GMT 2025
Edited
by admin
on Mon Mar 31 18:29:35 GMT 2025
Record UNII
59H4FCV1TF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEFAZODONE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
1-(3-(4-(M-CHLOROPHENYL)-1-PIPERAZINYL)PROPYL)-3-ETHYL-4-(2-PHENOXYETHYL)-.DELTA.(SUP 2)-1,2,4-TRIAZOLIN-5-ONE
Preferred Name English
nefazodone [INN]
Common Name English
NEFAZODONE [VANDF]
Common Name English
3H-1,2,4-TRIAZOL-3-ONE, 2-(3-(4-(3-CHLOROPHENYL)-1-PIPERAZINYL))PROPYL)-5-ETHYL-2,4-DIHYDRO-4-(2-PHENOXYETHYL)-
Common Name English
NEFAZODONE [MI]
Common Name English
Nefazodone [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
WHO-ATC N06AX06
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
NDF-RT N0000175696
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
WHO-VATC QN06AX06
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
LIVERTOX NBK548179
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
Code System Code Type Description
DRUG BANK
DB01149
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID2023357
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
IUPHAR
7247
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
RXCUI
31565
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY RxNorm
FDA UNII
59H4FCV1TF
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
DAILYMED
59H4FCV1TF
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
MERCK INDEX
m7793
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY Merck Index
CAS
83366-66-9
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
DRUG CENTRAL
1890
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
SMS_ID
100000084127
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
EVMPD
SUB09180MIG
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
MESH
C051752
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
LACTMED
Nefazodone
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
PUBCHEM
4449
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL623
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
NCI_THESAURUS
C61859
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
WIKIPEDIA
Nefazodone
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
INN
5432
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
CHEBI
7494
Created by admin on Mon Mar 31 18:29:35 GMT 2025 , Edited by admin on Mon Mar 31 18:29:35 GMT 2025
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
Structure of NEFAZODONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BMS-180492
METABOLITE ACTIVE -> PARENT
MAJOR
Structure of M-CHLOROPHENYLPIPERAZINE
METABOLITE ACTIVE -> PARENT
Structure of HYDROXYNEFAZODONE
METABOLITE ACTIVE -> PARENT
MAJOR
Structure of P-HYDROXY-META-CHLOROPHENYLPIPERAZINE
METABOLITE -> PARENT
Related Record Type Details
Structure of NEFAZODONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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