Pheniprazine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Pheniprazine
Accession Number
DB09250
Type
Small Molecule
Groups
Withdrawn
Description

Pheniprazine is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class that was used as an antidepressant in the 1960s. It was also used in the treatment of angina pectoris and schizophrenia. Pheniprazine has been largely discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Pheniprazine hydrochloride5B3OM8452C66-05-7HXCTUSBYMZQLKB-UHFFFAOYSA-N
International/Other Brands
Catron / Cavodil
Categories
UNII
37VKD7067M
CAS number
55-52-7
Weight
Average: 150.225
Monoisotopic: 150.115698459
Chemical Formula
C9H14N2
InChI Key
VXTWEDPZMSVFEF-UHFFFAOYSA-N
InChI
InChI=1S/C9H14N2/c1-8(11-10)7-9-5-3-2-4-6-9/h2-6,8,11H,7,10H2,1H3
IUPAC Name
(1-phenylpropan-2-yl)hydrazine
SMILES
CC(CC1=CC=CC=C1)NN

Pharmacology

Indication

For the treatment of depression, schizophrenia, and angina pectoris.

Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Pheniprazine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Pheniprazine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Pheniprazine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Pheniprazine.
4-MethoxyamphetaminePheniprazine may increase the hypertensive activities of 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Pheniprazine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolinePheniprazine may increase the hypertensive activities of 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbediterolThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Abediterol.
AcarbosePheniprazine may increase the hypoglycemic activities of Acarbose.
AcebutololPheniprazine may increase the hypotensive activities of Acebutolol.
Food Interactions
Not Available

References

General References
  1. LEAR TE, BROWNE MW, GREEVES JA: A controlled trial of cavodil (pheniprazine) in depression. J Ment Sci. 1962 Nov;108:856-58. [PubMed:13928843]
  2. SANDLER G: Clinical evaluation of pheniprazine in angina pectoris. Br Med J. 1961 Mar 18;1(5228):792-4. [PubMed:13746179]
  3. WICKSTROM L, HAHN N: [beta-Phenylisoprophlhydrazine (Catran) in schizophrenia]. Nord Med. 1962 Sep 13;68:1165-7. [PubMed:14000469]
External Links
PubChem Compound
5929
PubChem Substance
310265153
ChemSpider
5716
ChEBI
134773
ChEMBL
CHEMBL22498
Wikipedia
Pheniprazine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.75 mg/mLALOGPS
logP1.69ALOGPS
logP1.62ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)5.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area38.05 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.68 m3·mol-1ChemAxon
Polarizability17.47 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Alkylhydrazines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amphetamine or derivatives / Phenylpropane / Alkylhydrazine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Hydrazine derivative / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on October 23, 2015 22:06 / Updated on August 02, 2018 07:51