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

Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N2.H2O4S
Molecular Weight 234.273
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENELZINE SULFATE

SMILES

OS(O)(=O)=O.NNCCC1=CC=CC=C1

InChI

InChIKey=RXBKMJIPNDOHFR-UHFFFAOYSA-N
InChI=1S/C8H12N2.H2O4S/c9-10-7-6-8-4-2-1-3-5-8;1-5(2,3)4/h1-5,10H,6-7,9H2;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula C8H12N2
Molecular Weight 136.1943
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O4S
Molecular Weight 98.078
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.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf

Phenelzine is an irreversible non-selective inhibitor of monoamine oxidase. Although the exact mechanism of action has not been determined, it appears that the irreversible, nonselective inhibition of MAO by phenelzine relieves depressive symptoms by causing an increase in the levels of serotonin, norepinephrine, and dopamine in the neuron. Phenelzine is used for the treatment of major depressive disorder. Has also been used with some success in the management of bulimia nervosa.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nardil

Approved Use

Nardil is used for: Treating depression in patients who do not respond well to other medicines.

Launch Date

-2.70345601E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.14 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
19.8 ng/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
384.2 ng × h/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.75 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.6 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Disc. AE: Weakness, Lethargy...
AEs leading to
discontinuation/dose reduction:
Weakness
Lethargy
Dizziness
Gait abnormal NOS
Restlessness
Grand mal seizure
Hyperreflexia
Coma
Depression central nervous system
Sources:
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Disc. AE: Depressed level of consciousness, Seizures...
AEs leading to
discontinuation/dose reduction:
Depressed level of consciousness
Seizures
Tachycardia
Acute myocarditis (grade 5)
Sources: Page: p.1007
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Disc. AE: Muscular tone excessive, Hyperthermia...
AEs leading to
discontinuation/dose reduction:
Muscular tone excessive
Hyperthermia (severe)
Coma
Cardiovascular collapse
Acute renal failure
Hemolysis
Rhabdomyolysis
Disseminated intravascular coagulation
Sources: Page: p.1137/99
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.1
Disc. AE: Suicidal ideation...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Sources: Page: p.1
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.6
Disc. AE: Crisis hypertensive...
AEs leading to
discontinuation/dose reduction:
Crisis hypertensive
Sources: Page: p.6
AEs

AEs

AESignificanceDosePopulation
Coma Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Depression central nervous system Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Dizziness Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Gait abnormal NOS Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Grand mal seizure Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Hyperreflexia Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Lethargy Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Restlessness Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Weakness Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Depressed level of consciousness Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Seizures Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Tachycardia Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Acute myocarditis grade 5
Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Acute renal failure Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Cardiovascular collapse Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Coma Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Disseminated intravascular coagulation Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Hemolysis Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Muscular tone excessive Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Rhabdomyolysis Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Hyperthermia severe
Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Suicidal ideation Disc. AE
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.1
Crisis hypertensive Disc. AE
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.6
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no
unlikely [IC50 >897.2 uM]
yes [Ki 1.2 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Tox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The antidepressants fluoxetine, idazoxan and phenelzine alter corticotropin-releasing hormone and tyrosine hydroxylase mRNA levels in rat brain: therapeutic implications.
1992 Feb 14
Possible interaction between an MAOI and "ecstasy".
1992 Mar
Interactions between herbal medicines and prescribed drugs: a systematic review.
2001
Treatment of social phobia with antidepressants.
2001
Animal models for the study of antidepressant activity.
2001 Apr
Application of capillary electrophoresis with laser-induced fluorescence detection to the determination of biogenic amines and amino acids in brain microdialysate and homogenate samples.
2001 Apr 20
[Liver angiosarcoma in humans: epidemiologic considerations].
2001 Jan-Feb
The role of dopamine-metabolizing enzymes in the regulation of renal sodium excretion in the rat.
2001 Jul
Common effects of chronically administered antipanic drugs on brainstem GABA(A) receptor subunit gene expression.
2001 Jul
Sleep and sleep electroencephalogram in depressed patients treated with phenelzine.
2001 Mar
Inhibition of MAO-A fails to alter cocaine-induced increases in extracellular dopamine and norepinephrine in rat nucleus accumbens.
2001 Mar 5
The management of panic disorder.
2002
Panax ginseng: a systematic review of adverse effects and drug interactions.
2002
Effects of psychotropic drugs on seizure threshold.
2002
Remission in major depressive disorder: a comparison of pharmacotherapy, psychotherapy, and control conditions.
2002 Aug
Effects of antidepressants in rats trained to discriminate centrally administered isoproterenol.
2002 Aug
Antidepressants reduce phosphoinositide-specific phospholipase C (PI-PLC) activity and the mRNA and protein expression of selective PLC beta 1 isozyme in rat brain.
2002 Dec
Selective mutism: a review of the concept and treatment.
2002 Dec
Endogenous and endobiotic induced reactive oxygen species formation by isolated hepatocytes.
2002 Jan 1
The effects of tricyclic antidepressants on breast cancer risk.
2002 Jan 7
Clonidine potentiates the effects of tranylcypromine, phenelzine and two analogues in the forced swimming test in mice.
2002 May
World Federation of Societies of Biological Psychiatry (WFSBP) guidelines for the pharmacological treatment of anxiety, obsessive-compulsive and posttraumatic stress disorders.
2002 Oct
Different effects of phenelzine treatment on EEG topography in waking and sleep in depressed patients.
2002 Sep
Differential blockade of neuronal voltage-gated Na(+) and K(+) channels by antidepressant drugs.
2002 Sep 27
Pharmacological treatment of social anxiety disorder: a meta-analysis.
2003
Phenelzine efficacy in refractory social anxiety disorder: a case series.
2003
Phenelzine treatment increases transcription factor AP-2 levels in rat brain.
2003 Aug 28
Prior exposure to the elevated plus-maze sensitizes mice to the acute behavioral effects of fluoxetine and phenelzine.
2003 Jan 17
Comparing depression treatments.
2003 Jun
Rapid tryptophan depletion reverses phenelzine-induced suppression of REM sleep.
2003 Mar
Selectively bred Wistar-Kyoto rats: an animal model of depression and hyper-responsiveness to antidepressants.
2003 Nov
Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro.
2004 Dec
[Neurobiology and pharmacotherapy of social phobia].
2004 Jul-Aug
Coadministration of phenelzine and methylphenidate for treatment-resistant depression.
2004 Mar
Efficacy and tolerability of tranylcypromine versus phenelzine: a double-blind study in antidepressant-refractory depressed inpatients.
2004 Nov
Monoamine oxidase inhibitors, their structural analogues, and neuroprotection.
2004 Sep
Contribution of sleep research to the development of new antidepressants.
2005
Neuroendocrine predictors of the evolution of depression.
2005
Social anxiety disorder : current treatment recommendations.
2005
Screening antidepressants in the chick separation-stress paradigm.
2005 Aug
Brainstem levels of transcription factor AP-2 in rat are changed after treatment with phenelzine, but not with citalopram.
2005 Jan 21
Shy-Drager syndrome: multisystem atrophy with comorbid depression.
2005 Jan-Feb
A microarray study of MPP+-treated PC12 Cells: Mechanisms of toxicity (MOT) analysis using bioinformatics tools.
2005 Jul 15
Remission rates with 3 consecutive antidepressant trials: effectiveness for depressed outpatients.
2005 Jun
Chronic treatment with the monoamine oxidase inhibitor phenelzine increases hypothalamic-pituitary-adrenocortical activity in male C57BL/6 mice: relevance to atypical depression.
2005 Mar
Pharmacotherapy of social anxiety disorder: what does the evidence tell us?
2006
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine.
2006 Aug
Transdermal selegiline: the new generation of monoamine oxidase inhibitors.
2006 May
Tamoxifen protect against hydroxyl radical generation induced by phenelzine in rat striatum.
2006 May 1
13C magnetic resonance spectroscopy studies of alterations in glutamate neurotransmission.
2006 May 15
Patents

Sample Use Guides

Initial dose: The usual starting dose of NARDIL is one tablet (15 mg) three times a day. Early phase treatment: Dosage should be increased to at least 60 mg per day at a fairly rapid pace consistent with patient tolerance. It may be necessary to increase dosage up to 90 mg per day to obtain sufficient MAO inhibition. Many patients do not show a clinical response until treatment at 60 mg has been continued for at least 4 weeks.
Route of Administration: Oral
20 uM of Phenelzine inactivated all human liver microsomal CYP (CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A) but were most potent toward CYP3A and CYP2C19
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:34:24 UTC 2023
Edited
by admin
on Wed Jul 05 22:34:24 UTC 2023
Record UNII
2681D7P965
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENELZINE SULFATE
MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
PHENETHYLHYDRAZINE SULPHATE (1:1)
Systematic Name English
PHENELZINE SULFATE [VANDF]
Common Name English
PHENELZINE SULPHATE
Common Name English
HYDRAZINE, (2-PHENYLETHYL)-, SULPHATE (1:1)
Systematic Name English
PHENELZINE SULFATE [IARC]
Common Name English
NARDIL
Brand Name English
HYDRAZINE, (2-PHENYLETHYL)-, SULFATE (1:1)
Systematic Name English
Phenelzine sulfate [WHO-DD]
Common Name English
PHENELZINE ACID SULFATE [MI]
Common Name English
PHENELZINE SULFATE [ORANGE BOOK]
Common Name English
NSC-170957
Code English
PHENELZINE SULFATE [USP MONOGRAPH]
Common Name English
PHENELZINE SULFATE [USP-RS]
Common Name English
PHENELZINE SULFATE [MART.]
Common Name English
Phenethylhydrazine sulfate (1:1)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C667
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
Code System Code Type Description
MERCK INDEX
M8605
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY Merck Index
FDA UNII
2681D7P965
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
RXCUI
8124
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
205-856-0
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL1089
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID3021144
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
DRUG BANK
DBSALT000954
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
CAS
156-51-4
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
RS_ITEM_NUM
1517006
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
EVMPD
SUB03740MIG
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
NCI_THESAURUS
C47668
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
SMS_ID
100000092820
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
NSC
170957
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
PUBCHEM
61100
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
DAILYMED
2681D7P965
Created by admin on Wed Jul 05 22:34:24 UTC 2023 , Edited by admin on Wed Jul 05 22:34:24 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY