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

Details

Stereochemistry RACEMIC
Molecular Formula C9H14N2
Molecular Weight 150.2209
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENIPRAZINE

SMILES

CC(CC1=CC=CC=C1)NN

InChI

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

HIDE SMILES / InChI
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
138
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
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Withdrawn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Withdrawn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
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 50
Sex: M
Population Size: 1
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 (max)
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
Page: p.1959
unhealthy, 65
n = 1
Health Status: unhealthy
Condition: Hypertension
Age Group: 65
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
Page: p.1959
Disc. AE: Hepatotoxicity...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (grade 5)
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
Page: p.1959
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
Page: p.2
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
Page: p.2
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
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 50
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13993059
Hepatotoxicity grade 5
Disc. AE
18 mg 1 times / day multiple, oral (max)
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
Page: p.1959
unhealthy, 65
n = 1
Health Status: unhealthy
Condition: Hypertension
Age Group: 65
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13798229
Page: p.1959
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
Page: p.2
unhealthy
n = 1
Health Status: unhealthy
Condition: Depression
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13894598
Page: p.2
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
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
Sigma Aldrich
PH000293|ALDRICH
Sigma-Aldrich
PH000293_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/ph000293
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
eMolecules
6211138
eMolecules
95717200
PubMed

PubMed

TitleDatePubMed
Clinical evaluation of pheniprazine in angina pectoris.
1961 Mar 18
A controlled trial of cavodil (pheniprazine) in depression.
1962 Nov
[beta-Phenylisoprophlhydrazine (Catran) in schizophrenia].
1962 Sep 13
Toxic liver injuries.
1973 Aug
Design and biological evaluation of phenyl-substituted analogs of beta-phenylethylidenehydrazine.
2005 Jul 15
Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration.
2005 Jun
Species differences in the selective inhibition of monoamine oxidase (1-methyl-2-phenylethyl)hydrazine and its potentiation by cyanide.
2007 Oct
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:39 GMT 2023
Record UNII
37VKD7067M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENIPRAZINE
INN   MI   WHO-DD  
INN  
Official Name English
Pheniprazine [WHO-DD]
Common Name English
pheniprazine [INN]
Common Name English
PHENIPRAZINE DL-FORM [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C667
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
Code System Code Type Description
DRUG CENTRAL
2131
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
EVMPD
SUB09767MIG
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
DRUG BANK
DB09250
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
NCI_THESAURUS
C80967
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
PUBCHEM
5929
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
FDA UNII
37VKD7067M
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-236-6
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
CAS
55-52-7
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
MERCK INDEX
m882
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY Merck Index
CAS
52031-11-5
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
SUPERSEDED
EPA CompTox
DTXSID6043838
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
MESH
C084776
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
SMS_ID
100000082256
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
INN
981
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
WIKIPEDIA
PHENIPRAZINE
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL22498
Created by admin on Fri Dec 15 15:08:39 GMT 2023 , Edited by admin on Fri Dec 15 15:08:39 GMT 2023
PRIMARY
Related Record Type Details
Structure of PHENIPRAZINE, (R)-
ENANTIOMER -> RACEMATE
Structure of PHENIPRAZINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of PHENIPRAZINE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of PHENIPRAZINE
ACTIVE MOIETY
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