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

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(Cl)=CC=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

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
3828
Curator's Comment: antidepressant

Originator

Bristol-Myers Squibb
145
Curator's Comment: # Bristol-Myers Squibb

Approval Year

1994
155
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2760
 5.8 nM [Ki]
Antagonist
2760
 290.0 nM [Ki]
Antagonist
2760
 5.5 nM [Ki]
Antagonist
2760
 84.0 nM [Ki]
Antagonist
2760
 52.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
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

1.06358401E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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
5.2 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
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
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
n = 12
Health Status: unhealthy
Condition: hepatic cirrhosis
Age Group: adult
Sex: unknown
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: renal impairment
Age Group: adult
Sex: unknown
Population Size: 12
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 (mean)
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
n = 19
Health Status: unhealthy
Condition: Posttraumatic stress disorder
Age Group: adult
Sex: M
Population Size: 19
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 (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
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/
Page: Table 1
600 mg 1 times / day steady, oral (max)
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/
Page: Table 2
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 2
Other AEs: Somnolence...
Other AEs:
Somnolence (25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 2
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
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/
Page: Table 1
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
n = 12
Health Status: healthy
Age Group: elderly
Sex: unknown
Population Size: 12
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
n = 12
Health Status: healthy
Age Group: younger
Sex: unknown
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: hepatic cirrhosis
Age Group: adult
Sex: unknown
Population Size: 12
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
n = 12
Health Status: unhealthy
Condition: renal impairment
Age Group: adult
Sex: unknown
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Diarrhea 42%
430 mg 1 times / day steady, oral (mean)
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
n = 19
Health Status: unhealthy
Condition: Posttraumatic stress disorder
Age Group: adult
Sex: M
Population Size: 19
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
Dry mouth 42%
430 mg 1 times / day steady, oral (mean)
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
n = 19
Health Status: unhealthy
Condition: Posttraumatic stress disorder
Age Group: adult
Sex: M
Population Size: 19
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
Headaches 53%
430 mg 1 times / day steady, oral (mean)
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
n = 19
Health Status: unhealthy
Condition: Posttraumatic stress disorder
Age Group: adult
Sex: M
Population Size: 19
Sources:
https://pubmed.ncbi.nlm.nih.gov/10817106/
Light headedness 10%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Asthenia 11%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Constipation 14%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Dizziness 17%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Nausea 22%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Dry mouth 25%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Abnormal vision 7%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Confusion 7%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Blurred vision 9%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Somnolence 25%
600 mg 1 times / day steady, oral (max)
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/
Page: Table 2
unhealthy, adult
n = 394
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 394
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 2
Agitation 1.2%
Disc. AE
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Asthenia 1.3%
Disc. AE
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Insomnia 1.5%
Disc. AE
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Somnolence 1.5%
Disc. AE
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Dizziness 1.9%
Disc. AE
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Headache 2.9%
Disc. AE
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
Nausea 3.5%
Disc. AE
600 mg 1 times / day steady, oral (max)
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/
Page: Table 1
unhealthy, adult
n = 565
Health Status: unhealthy
Condition: major depression
Age Group: adult
Sex: unknown
Population Size: 565
Sources:
https://pubmed.ncbi.nlm.nih.gov/8876863/
Page: Table 1
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
n = 12
Health Status: healthy
Age Group: elderly
Sex: unknown
Population Size: 12
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
n = 12
Health Status: healthy
Age Group: younger
Sex: unknown
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/8665999/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1579

substrate
1709
inhibitor
1837

substrate
1193
inhibitor
1599

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1509

P-gp
1437

BSEP
401
P-gp
1527
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1673
 no
CYP2D6
1875
 weak
P-gp
1626
 yes [IC50 4.7 uM]
BSEP
402
 yes [IC50 9 uM]
CYP3A4
1909
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1527
 no
CYP2D6
1193
 yes
mCPP
2
CYP3A4
1709
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1632
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
MolPort
MolPort-003-983-466
https://www.molport.com/shop/molecule-link/MolPort-003-983-466
eMolecules
592758
https://www.emolecules.com/cgi-bin/more?vid=592758
PubMed

PubMed

TitleDatePubMed
Interactions between herbal medicines and prescribed drugs: a systematic review.
2001
Third-generation antidepressants: do they offer advantages over the SSRIs?
2001
Long-term treatment of recurrent and chronic depression.
2001
Pharmacokinetically induced benzodiazepine withdrawal.
2001 Autumn
A probable interaction between a very low-dose oral contraceptive and the antidepressant nefazodone: a case report.
2001 Dec
Possible interaction of zopiclone and nefazodone.
2001 Nov
Pharmacotherapy for post-traumatic stress disorder: a comprehensive review.
2001 Oct
An open-label, 12-week clinical and sleep EEG study of nefazodone in chronic combat-related posttraumatic stress disorder.
2001 Oct
[Pharmacotherapeutical approaches to insomnia patients with cardiac diseases and after heart transplantation].
2001 Oct
Charleston Antidepressant Drug Interactions Surveillance Program (CADISP).
2001 Spring
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
Pharmacology of antidepressants: focus on nefazodone.
2002
Prevalence of sexual dysfunction among newer antidepressants.
2002 Apr
Serzone. Beware of dangerous liver problems.
2002 Apr
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 Apr
Human CYP3A4 and the metabolism of nefazodone and hydroxynefazodone by human liver microsomes and heterologously expressed enzymes.
2002 Apr
Nefazodone and liver damage.
2002 Aug
Sexual function and satisfaction in the treatment of chronic major depression with nefazodone, psychotherapy, and their combination.
2002 Aug
Differential effects of amitriptyline, nefazodone and paroxetine on performance and brain indices of visual selective attention and working memory.
2002 Aug
An open pilot study of nefazodone in depression with anger attacks: relationship between clinical response and receptor binding.
2002 Dec 30
Hepatotoxicity associated with the new antidepressants.
2002 Feb
Does psychosocial functioning improve independent of depressive symptoms? A comparison of nefazodone, psychotherapy, and their combination.
2002 Jan 15
[Acute liver failure in nefazodone therapy? A case report].
2002 Jul
An open-label clinical trial of nefazodone in hypochondriasis.
2002 Jul-Aug
Optimizing antidepressant treatment: efficacy and tolerability.
2002 Jun
Differential effects of nefazodone and cognitive behavioral analysis system of psychotherapy on insomnia associated with chronic forms of major depression.
2002 Jun
Randomised controlled study of sleep after nefazodone or paroxetine treatment in out-patients with depression.
2002 Jun
New antidepressants in the treatment of neuropathic pain. A review.
2002 Mar
From the Food and Drug Administration.
2002 Mar 6
Evaluating changes in sexual functioning in depressed patients: sensitivity to change of the CSFQ.
2002 Mar-Apr
Nefazodone treatment of dysthymic disorder an open, long-term, prospective pilot study.
2002 May
Pharmacological interactions of statins.
2002 May
Symptomatic and syndromal anxiety in chronic forms of major depression: effect of nefazodone, cognitive behavioral analysis system of psychotherapy, and their combination.
2002 May
Hepatic adverse reactions associated with nefazodone.
2002 May
Loratadine/nefazodone interaction.
2002 May
Effects of smoked marijuana in healthy and HIV + marijuana smokers.
2002 Nov
Combination therapy in the treatment of major depressive disorder complicated by fibromyalgia and menopause.
2002 Nov-Dec
Nefazodone alters NPY immunostaining in rat arcuate-paraventricular projection without changes in food intake and body weight.
2002 Oct
Antidepressant-induced sexual dysfunction.
2002 Oct
Effects of nefazodone on voluntary ethanol consumption induced by isolation stress in young and aged rats.
2002 Oct
[Pharmacological justification for the use of new antidepressant drugs].
2002 Sep
Reversible penile priapism associated with nefazodone.
2002 Sep
Rhabdomyolysis with simvastatin and nefazodone.
2002 Sep
Nefazodone and cyp450 3a4 interactions with cyclosporine and tacrolimus1.
2002 Sep 15
Enhanced resolution triple-quadrupole mass spectrometry for fast quantitative bioanalysis using liquid chromatography/tandem mass spectrometry: investigations of parameters that affect ruggedness.
2003
Nefazodone decreases anxiety during marijuana withdrawal in humans.
2003 Jan
Patents

Patents

20010014678
18
JP2002511409A
23
JP2002528505A
2
JP2006505569A
69
JP2007514770A
75
JP2007516170A
14
JP2011508748A
29
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)
Name Type Language
NEFAZODONE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
NEFAZODONE HYDROCHLORIDE [MI]
Common Name English
NEFAZODONE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
BMY 13754
Code English
NEFAZODONE HYDROCHLORIDE [USP IMPURITY]
Common Name English
NEFAZODONE HYDROCHLORIDE [MART.]
Common Name English
NSC-760344
Code English
MJ 13,754-1
Code English
NEFAZODONE HYDROCHLORIDE [USP-RS]
Common Name English
NEFAZODONE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
2-(3-(4-(3-CHLOROPHENYL)-1-PIPERAZINYL)PROPYL)-5-ETHYL-2,4-DIHYDRO-4-(2-PHENOXYETHYL)-3H-1,2,4-TRIAZOL-3-ONE MONOHYDROCHLORIDE
Systematic Name English
BMY-13754
Code English
NEFAZODONE HYDROCHLORIDE [USAN]
Common Name English
Nefazodone hydrochloride [WHO-DD]
Common Name English
NEFAZODONE HCL
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)-, MONOHYDROCHLORIDE
Systematic Name English
MJ-13754-1
Code English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1457902
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
EVMPD
SUB03399MIG
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
DRUG BANK
DBSALT000406
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
NSC
760344
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
CAS
82752-99-6
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
EPA CompTox
DTXSID8046088
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
ChEMBL
CHEMBL623
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
RXCUI
236082
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY RxNorm
FDA UNII
27X63J94GR
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
NCI_THESAURUS
C29283
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
SMS_ID
100000085692
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
DAILYMED
27X63J94GR
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
CHEBI
7495
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
MERCK INDEX
M7793
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY Merck Index
PUBCHEM
54911
Created by admin on Wed Jul 05 23:53:44 UTC 2023 , Edited by admin on Wed Jul 05 23:53:44 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of NEFAZODONE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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