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Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N2
Molecular Weight 136.1943
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENELZINE

SMILES

NNCCC1=CC=CC=C1

InChI

InChIKey=RMUCZJUITONUFY-UHFFFAOYSA-N
InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2

HIDE SMILES / InChI

Molecular Formula C8H12N2
Molecular Weight 136.1943
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
76.3 nM [IC50]
30.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nardil

Cmax

ValueDoseCo-administeredAnalytePopulation
10.14 ng/mL
15 mg single, oral
PHENELZINE plasma
Homo sapiens
19.8 ng/mL
30 mg single, oral
PHENELZINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
384.2 ng × h/mL
15 mg single, oral
PHENELZINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
9.75 h
15 mg single, oral
PHENELZINE plasma
Homo sapiens
11.6 h
30 mg single, oral
PHENELZINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
O408N561GF
Record Status Validated (UNII)
Record Version