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 234.2742
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENELZINE SULFATE

SMILES

c1ccc(cc1)CCNN.OS(=O)(=O)O

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 136.1946
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O4S
Molecular Weight 98.0796
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
Abuse of monoamine oxidase inhibitors.
1992
Depression after cyproheptadine: MAO treatment.
1992 Jun 1
Possible interaction between an MAOI and "ecstasy".
1992 Mar
Phenelzine-induced sexual dysfunction treated with sildenafil.
1999 Apr-Jun
[Clinical case of the month. Mental confusion due to the administration of tramadol in a patient treated with MOAI].
1999 Dec
Treatment of social phobia with antidepressants.
2001
Current status of psychotherapeutic interventions for social phobia.
2001
Social phobia: etiology, neurobiology, and treatment.
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
[The safety of herbal medicines in the psychiatric practice].
2001 Aug
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
Effect of chronic phenelzine treatment on REM sleep: report of three patients.
2001 Nov
Synthesis of N-propargylphenelzine and analogues as neuroprotective agents.
2001 Oct 22
Influence of different antidepressant drugs on the effect of chronic variable stress on restraint-induced dopamine release in frontal cortex.
2001 Sep
Panax ginseng: a systematic review of adverse effects and drug interactions.
2002
Effects of psychotropic drugs on seizure threshold.
2002
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
Effects of the antidepressant/antipanic drug phenelzine and its putative metabolite phenylethylidenehydrazine on extracellular gamma-aminobutyric acid levels in the striatum.
2002 Jan 1
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
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
Effect of antidepressants on GABA(B) receptor function and subunit expression in rat hippocampus.
2004 Oct 15
Modafinil augmentation of phenelzine for residual fatigue in dysthymia.
2004 Sep
Sleep and psychiatry.
2005
Herb-drug interactions: a literature review.
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
Chronic treatment with the monoamine oxidase inhibitor phenelzine increases hypothalamic-pituitary-adrenocortical activity in male C57BL/6 mice: relevance to atypical depression.
2005 Mar
Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.
2005 Oct
Pharmacotherapy of social anxiety disorder: what does the evidence tell us?
2006
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine.
2006 Aug
Rapid identification of P-glycoprotein substrates and inhibitors.
2006 Dec
The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms.
2006 Jan
Effects of monoamine oxidase inhibitors on cocaine discrimination in rats.
2006 Mar
Modeling anxiety-like states: pharmacological characterization of the chick separation stress paradigm.
2006 Nov
Aldehyde load in ischemia-reperfusion brain injury: neuroprotection by neutralization of reactive aldehydes with phenelzine.
2006 Nov 29
Sustained effects of phenelzine and tranylcypromine on orthostatic challenge in antidepressant-refractory depression.
2006 Oct
Antidepressants and inflammatory bowel disease: a systematic review.
2006 Sep 20
Antidepressant therapy in tinnitus.
2007 Apr
Successful use of phenelzine in treatment-resistant panic disorder.
2007 Feb
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 Sat Jun 26 03:44:55 UTC 2021
Edited
by admin
on Sat Jun 26 03:44:55 UTC 2021
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
PHENELZINE SULFATE [WHO-DD]
Common Name English
HYDRAZINE, (2-PHENYLETHYL)-, SULFATE (1:1)
Systematic Name English
PHENELZINE ACID SULFATE [MI]
Common Name English
PHENELZINE SULFATE [ORANGE BOOK]
Common Name English
NSC-170957
Code English
PHENELZINE SULFATE [USP-RS]
Common Name English
PHENELZINE SULFATE [USP]
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 Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
Code System Code Type Description
MERCK INDEX
M8605
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY Merck Index
FDA UNII
2681D7P965
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
RXCUI
8124
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
205-856-0
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
ChEMBL
CHEMBL1089
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
EPA CompTox
156-51-4
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
USP_CATALOG
1517006
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY USP-RS
DRUG BANK
DBSALT000954
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
CAS
156-51-4
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
EVMPD
SUB03740MIG
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
NCI_THESAURUS
C47668
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
PUBCHEM
61100
Created by admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY