Iproclozide

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

Identification

Name
Iproclozide
Accession Number
DB09247
Type
Small Molecule
Groups
Withdrawn
Description

Iproclozide is an irreversible and selective monoamine oxidase inhibitor (MAOI) of the hydrazine chemical class that was used as an antidepressant, but has since been discontinued. It has been known to cause fulminant hepatitis and there have been at least three reported fatalities due to administration of the drug.

Structure
Thumb
Synonyms
Not Available
External IDs
PC-603
International/Other Brands
Sinderesin / Sursum
Categories
UNII
1II9D6CB3J
CAS number
3544-35-2
Weight
Average: 242.7
Monoisotopic: 242.0822054
Chemical Formula
C11H15ClN2O2
InChI Key
GGECDTUJZOXAAR-UHFFFAOYSA-N
InChI
InChI=1S/C11H15ClN2O2/c1-8(2)13-14-11(15)7-16-10-5-3-9(12)4-6-10/h3-6,8,13H,7H2,1-2H3,(H,14,15)
IUPAC Name
2-(4-chlorophenoxy)-N'-(propan-2-yl)acetohydrazide
SMILES
CC(C)NNC(=O)COC1=CC=C(Cl)C=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 adverse effects can be increased when Iproclozide is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Iproclozide is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Iproclozide is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Iproclozide.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Iproclozide.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Iproclozide is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Iproclozide.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Iproclozide is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Iproclozide.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Iproclozide.
Food Interactions
Not Available

References

General References
  1. Suerinck A, Suerinck E: [Depressive states in a sanatorium milieu and monoamine oxidase inhibitors. (Therapeutic results by the combination of iproclozide and chlordiazepoxide). Apropos of 146 cases]. J Med Lyon. 1966 Apr 5;47(96):573-86. [PubMed:5930723]
  2. Pessayre D, de Saint-Louvent P, Degott C, Bernuau J, Rueff B, Benhamou JP: Iproclozide fulminant hepatitis. Possible role of enzyme induction. Gastroenterology. 1978 Sep;75(3):492-6. [PubMed:680506]
External Links
KEGG Drug
D07338
PubChem Compound
19063
PubChem Substance
310265150
ChemSpider
17998
ChEBI
134988
ChEMBL
CHEMBL91238
Wikipedia
Iproclozide
ATC Codes
N06AF06 — Iproclozide

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 Solubility0.2 mg/mLALOGPS
logP1.91ALOGPS
logP1.79ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)11.58ChemAxon
pKa (Strongest Basic)3.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area50.36 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.21 m3·mol-1ChemAxon
Polarizability25.21 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 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 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 / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Carboxylic acid hydrazides / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Phenoxy compound / Phenol ether / Alkyl aryl ether / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Carboxylic acid hydrazide / Carboxylic acid derivative
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on October 23, 2015 16:25 / Updated on November 02, 2018 07:00