Phenoxypropazine

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

Identification

Name
Phenoxypropazine
Accession Number
DB09251
Type
Small Molecule
Groups
Withdrawn
Description

Phenoxypropazine is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine family. It was introduced as an antidepressant in 1961, but was subsequently withdrawn in 1966 due to hepatotoxicity concerns.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Drazine
Categories
UNII
8E92V52324
CAS number
3818-37-9
Weight
Average: 166.224
Monoisotopic: 166.110613079
Chemical Formula
C9H14N2O
InChI Key
QNEXFJFTGQBXBJ-UHFFFAOYSA-N
InChI
InChI=1S/C9H14N2O/c1-8(11-10)7-12-9-5-3-2-4-6-9/h2-6,8,11H,7,10H2,1H3
IUPAC Name
(1-phenoxypropan-2-yl)hydrazine
SMILES
[H]N([H])N([H])C(C)COC1=CC=CC=C1

Pharmacology

Indication

For the treatment of depression.

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
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Phenoxypropazine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Phenoxypropazine is combined with (S)-Warfarin.
2,4-thiazolidinedionePhenoxypropazine may increase the hypoglycemic activities of 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetaminePhenoxypropazine may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetaminePhenoxypropazine may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetaminePhenoxypropazine may increase the hypertensive activities of 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetaminePhenoxypropazine may increase the hypertensive activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Phenoxypropazine is combined with 4-hydroxycoumarin.
4-MethoxyamphetaminePhenoxypropazine 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 Phenoxypropazine.
Food Interactions
Not Available

References

General References
  1. LEAHY MR, ROSE JT, PLOWMAN R: A preliminary study of phenoxypropazine in the treatment of depression. Am J Psychiatry. 1963 Apr;119:986-7. [PubMed:13928824]
  2. IMLAH NW: Preliminary report on phenoxypropazine. Am J Psychiatry. 1963 May;119:1091-2. [PubMed:13956423]
  3. ROSE JT, LEAHY MR, PLOWMAN R: A COMPARISON OF PHENOXYPROPAZINE AND AMYTRYPTILINE IN DEPRESSION. Am J Psychiatry. 1963 Oct;120:393-5. [PubMed:14069469]
External Links
PubChem Compound
71467
PubChem Substance
310265154
ChemSpider
64548
ChEBI
134799
ChEMBL
CHEMBL1909286
Wikipedia
Phenoxypropazine

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 Solubility6.03 mg/mLALOGPS
logP1.37ALOGPS
logP1.25ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)5.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area47.28 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.87 m3·mol-1ChemAxon
Polarizability18.67 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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 phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Alkyl aryl ethers / Alkylhydrazines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Alkylhydrazine / Ether / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on October 23, 2015 22:12 / Updated on November 02, 2018 07:00