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

Details

Stereochemistry RACEMIC
Molecular Formula C9H14N2.ClH
Molecular Weight 186.682
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENIPRAZINE HYDROCHLORIDE

SMILES

Cl.CC(CNN)C1=CC=CC=C1

InChI

InChIKey=VATMJXRAQUGDSQ-UHFFFAOYSA-N
InChI=1S/C9H14N2.ClH/c1-8(7-11-10)9-5-3-2-4-6-9;/h2-6,8,11H,7,10H2,1H3;1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C9H14N2
Molecular Weight 150.2209
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

PHENIPRAZINE is a monoamine oxidase inhibitor of the hydrazine chemical class that was used for the treatment of depression, schizophrenia, and also as a long-acting coronary vasodilator in patients suffering from angina pectoris. PHENIPRAZINE was discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis.

Approval Year

1959
143
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Catron

Approved Use

Unknown
Primary
Withdrawn
Catron

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
9 mg 1 times / day multiple, oral
Recommended
Dose: 9 mg, 1 times / day
Route: oral
Route: multiple
Dose: 9 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13993059
unhealthy, 50
Health Status: unhealthy
Age Group: 50
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/13993059
Disc. AE: Amblyopia...
AEs leading to
discontinuation/dose reduction:
Amblyopia
Sources:
https://pubmed.ncbi.nlm.nih.gov/13993059
18 mg 1 times / day multiple, oral
Studied dose
Dose: 18 mg, 1 times / day
Route: oral
Route: multiple
Dose: 18 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
unhealthy, 65
Health Status: unhealthy
Age Group: 65
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
Disc. AE: Hepatotoxicity...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (grade 5)
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Disc. AE: Blurred vision, Scotoma...
AEs leading to
discontinuation/dose reduction:
Blurred vision
Scotoma
Ataxia
Weakness in extremity
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Disc. AE: Maculo-papular rash, Blurred vision...
AEs leading to
discontinuation/dose reduction:
Maculo-papular rash
Blurred vision
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
AEs

AEs

AESignificanceDosePopulation
Amblyopia Disc. AE
9 mg 1 times / day multiple, oral
Recommended
Dose: 9 mg, 1 times / day
Route: oral
Route: multiple
Dose: 9 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13993059
unhealthy, 50
Health Status: unhealthy
Age Group: 50
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/13993059
Hepatotoxicity grade 5
Disc. AE
18 mg 1 times / day multiple, oral
Studied dose
Dose: 18 mg, 1 times / day
Route: oral
Route: multiple
Dose: 18 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
unhealthy, 65
Health Status: unhealthy
Age Group: 65
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
Ataxia Disc. AE
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Blurred vision Disc. AE
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Scotoma Disc. AE
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Weakness in extremity Disc. AE
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Blurred vision Disc. AE
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Maculo-papular rash Disc. AE
25 mg 1 times / day multiple, oral
Highest studied dose
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P01FJMD
AAA Chemistry
AR-1J0745
ABI Chem
AC1L1LFR
ABI Chem
AC1Q4U37
AKOS
AKOS026733800
Aurora Fine Chemicals LLC
A14.691.695
http://online.aurorafinechemicals.com/info?ID=A14.691.695
BOC Sciences
55-52-7
Chemhere
Achem131291
Chemhere
Pubchem32673
Chemieliva Pharmaceutical Co., Ltd
PBCM0640340
Chemspace
CSC011792917
Chemspace
CSC015460097
Chemspace
CSC015884722
eMolecules
6211138
eMolecules
95717200
Enamine
BBV-36839591
Enamine
BBV-38367571
Enamine
BBV-38367572
Enamine
EN300-1588840
Enamine
EN300-274949
Lab Seeker
SC-39255
MolPort
MolPort-006-110-107
MolPort
MolPort-045-971-481
NCI Plated 2007
17766
NovoSeek
5929
Sigma-Aldrich
PH000293_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/ph000293
Sigma Aldrich
PH000293
Sigma Aldrich
PH000293|ALDRICH
Smolecule
S563124
https://www.smolecule.com/products/s563124
StruChem
SC-39255
THE BioTek
bt-434896
https://www.thebiotek.com/product/others/bt-434896
ZINC
ZINC000019166939
http://zinc15.docking.org/substances/ZINC000019166939
ZINC
ZINC000019167667
http://zinc15.docking.org/substances/ZINC000019167667
PubMed

PubMed

TitleDatePubMed
Species differences in the selective inhibition of monoamine oxidase (1-methyl-2-phenylethyl)hydrazine and its potentiation by cyanide.
2007-10
Design and biological evaluation of phenyl-substituted analogs of beta-phenylethylidenehydrazine.
2005-07-15
Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration.
2005-06
Toxic liver injuries.
1973-08
A controlled trial of cavodil (pheniprazine) in depression.
1962-11
[beta-Phenylisoprophlhydrazine (Catran) in schizophrenia].
1962-09-13
Clinical evaluation of pheniprazine in angina pectoris.
1961-03-18
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:28:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:28:14 GMT 2025
Record UNII
5B3OM8452C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENIPRAZINE HYDROCHLORIDE
Common Name English
CATRAL
Preferred Name English
JB-516
Code English
CATRONIAZID
Brand Name English
CAVODIL
Brand Name English
NSC-78085
Code English
CATRON
Brand Name English
PHENIPRAZINE DL-FORM HYDROCHLORIDE [MI]
Common Name English
NSC-17766
Code English
CATRON HYDROCHLORIDE
Brand Name English
PHENIPRAZINE HCL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C667
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
Code System Code Type Description
MERCK INDEX
m882
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY Merck Index
DRUG BANK
DBSALT001273
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL22498
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
NSC
78085
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
CAS
54779-57-6
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
SUPERSEDED
FDA UNII
5B3OM8452C
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
CAS
15573-15-6
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
NON-SPECIFIC STOICHIOMETRY
NCI_THESAURUS
C73612
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
NSC
17766
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
PUBCHEM
6182
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
CAS
66-05-7
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID8021149
Created by admin on Mon Mar 31 18:28:14 GMT 2025 , Edited by admin on Mon Mar 31 18:28:14 GMT 2025
PRIMARY
Related Record Type Details
Structure of PHENIPRAZINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PHENIPRAZINE
ACTIVE MOIETY
NIH
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