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Details

Stereochemistry ACHIRAL
Molecular Formula C12H13N3O2
Molecular Weight 231.2505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOCARBOXAZID

SMILES

CC1=CC(=NO1)C(=O)NNCC2=CC=CC=C2

InChI

InChIKey=XKFPYPQQHFEXRZ-UHFFFAOYSA-N
InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)

HIDE SMILES / InChI

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

Isocarboxazid (Marplan, Marplon, Enerzer) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class used as an antidepressant. In vivo and in vitro studies demonstrated inhibition of MAO in the brain, heart, and liver. Depression is a complicated disease that is not fully understood. It is thought that depression may be linked to an imbalance of chemicals within the brain. When depression occurs, there may be a decrease in the amount of chemicals released from nerve cells in the brain. These chemicals are called monoamines. Monoamines are broken down by a chemical called monoamine oxidase. Isocarboxazid prevents monoamine oxidase from breaking down the monoamines. This results in an increased amount of active monoamines in the brain. By increasing the amount of monoamines in the brain, the imbalance of chemicals thought to be caused by depression is altered. This helps relieve the symptoms of depression. Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (MAO) in the nervous system. MAO subtypes A and B are involved in the metabolism of serotonin and catecholamine neurotransmitters such as epinephrine, norepinephrine, and dopamine. Isocarboxazid, as a nonselective MAO inhibitor, binds irreversibly to monoamine oxidase–A (MAO-A) and monoamine oxidase–B (MAO-B). The reduced MAO activity results in an increased concentration of these neurotransmitters in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. This increased availability of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors. May be used to treat major depressive disorder.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
128.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Marplan

Approved Use

Marplan is indicated for the treatment of depression. Because of its potentially serious side effects, Marplan is not an antidepressant of first choice in the treatment of newly diagnosed depressed patients.

Launch Date

-3.31603214E11
Doses

Doses

DosePopulationAdverse events​
80 mg 1 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 18 - 65 years
n = 3
Health Status: unhealthy
Condition: depression
Age Group: 18 - 65 years
Population Size: 3
Sources:
Disc. AE: Hyperreflexia, Hyperexcitability...
AEs leading to
discontinuation/dose reduction:
Hyperreflexia (1 patient)
Hyperexcitability (1 patient)
Agitation (1 patient)
Weakness (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Agitation 1 patient
Disc. AE
80 mg 1 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 18 - 65 years
n = 3
Health Status: unhealthy
Condition: depression
Age Group: 18 - 65 years
Population Size: 3
Sources:
Hyperexcitability 1 patient
Disc. AE
80 mg 1 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 18 - 65 years
n = 3
Health Status: unhealthy
Condition: depression
Age Group: 18 - 65 years
Population Size: 3
Sources:
Hyperreflexia 1 patient
Disc. AE
80 mg 1 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 18 - 65 years
n = 3
Health Status: unhealthy
Condition: depression
Age Group: 18 - 65 years
Population Size: 3
Sources:
Weakness 1 patient
Disc. AE
80 mg 1 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 18 - 65 years
n = 3
Health Status: unhealthy
Condition: depression
Age Group: 18 - 65 years
Population Size: 3
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Use of isocarboxazid in hypertensive patients.
1966 Jul-Aug
Linoleic acid in the treatment of lithium toxicity and familial tremor.
1980 Apr
Treatment of lithium-induced tremor and familial essential tremor with essential fatty acids.
1981
Acute lithium-induced tremor.
1983 Jul
The importance of dose in isocarboxazid therapy.
1984 Jul
Mania after withdrawal of isocarboxazid.
1985 Dec
Mania induced by tricyclic-MAOI combination therapy in bipolar treatment-resistant disorder: case reports.
1986 Jan
A trial of isocarboxazid in the treatment of bulimia nervosa.
1988 Dec
Sertraline and isocarboxazid cause a serotonin syndrome.
1994 Apr
Serotonin syndrome.
1995 Feb
Toxic interaction of venlafaxine and isocarboxazide.
1995 Nov 11
Synthesis of novel N-substituted imidazolecarboxylic acid hydrazides as monoamine oxidase inhibitors.
2005 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Dosage should be started with one tablet (10 mg) of Marplan (Isocarboxazid) twice daily. If tolerated, dosage may be increased by increments of one tablet (10 mg) every 2 to 4 days to achieve a dosage of four tablets daily (40 mg) by the end of the first week of treatment. Dosage can then be increased by increments of up to 20 mg/week, if needed and tolerated, to a maximum recommended dosage of 60 mg/day. Daily dosage should be divided into two to four dosages.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ISOCARBOXAZID
INN   MART.   MI   ORANGE BOOK   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
ISOCARBOXAZID [ORANGE BOOK]
Common Name English
MARPLAN
Brand Name English
ISOCARBOXAZID [MI]
Common Name English
ISOCARBOXAZID [MART.]
Common Name English
Isocarboxazid [WHO-DD]
Common Name English
RO 5-0831
Code English
NSC-169893
Code English
RO-5-0831
Code English
ISOCARBOXAZIDE
Common Name English
3-ISOXAZOLECARBOXYLIC ACID, 5-METHYL-, 2-(PHENYLMETHYL)HYDRAZIDE
Common Name English
5-Methyl-3-isoxazolecarboxylic acid 2-benzylhydrazide
Common Name English
ISOCARBOXAZID [USP-RS]
Common Name English
isocarboxazid [INN]
Common Name English
ENERZER
Brand Name English
Classification Tree Code System Code
WHO-ATC N06AF01
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
NDF-RT N0000000184
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
NDF-RT N0000175744
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
LIVERTOX NBK548518
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
WHO-VATC QN06AF01
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
NCI_THESAURUS C667
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
NCI_THESAURUS C265
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
Code System Code Type Description
MESH
D007520
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
DRUG BANK
DB01247
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
RXCUI
6011
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY RxNorm
MERCK INDEX
M6472
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY Merck Index
NSC
169893
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
IUPHAR
7204
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
NCI_THESAURUS
C47573
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
ChEMBL
CHEMBL1201168
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
INN
1071
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
FDA UNII
34237V843T
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
CAS
59-63-2
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
WIKIPEDIA
ISOCARBOXAZID
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
EVMPD
SUB08313MIG
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
DRUG CENTRAL
1490
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
EPA CompTox
DTXSID4023171
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
DAILYMED
34237V843T
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
LACTMED
Isocarboxazid
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
PUBCHEM
3759
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-438-4
Created by admin on Fri Dec 16 16:02:46 UTC 2022 , Edited by admin on Fri Dec 16 16:02:46 UTC 2022
PRIMARY