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Identification
NameIproniazid
Accession NumberDB04818
Typesmall molecule
Groupswithdrawn
Description

Withdrawn from the Canadian market in July 1964 due to interactions with food products containing tyrosine.

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
IpronidA.F.I.
MarsilidGenopharm
RivivolZambeletti
Brand mixturesNot Available
CategoriesNot Available
CAS number54-92-2
WeightAverage: 179.219
Monoisotopic: 179.105862053
Chemical FormulaC9H13N3O
InChI KeyNYMGNSNKLVNMIA-UHFFFAOYSA-N
InChI
InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13)
IUPAC Name
N'-(propan-2-yl)pyridine-4-carbohydrazide
SMILES
CC(C)NNC(=O)C1=CC=NC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassPyridinecarboxylic Acids and Derivatives
Direct parentPyridinecarboxylic Acids and Derivatives
Alternative parentsCarboxylic Acid Hydrazides; Enolates; Carboxylic Acid Amides; Polyamines; Hydrazines and Derivatives
Substituentscarboxamide group; carboxylic acid hydrazide; carboxylic acid derivative; enolate; polyamine; hydrazine derivative; amine; organonitrogen compound
Classification descriptionThis compound belongs to the pyridinecarboxylic acids and derivatives. These are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.
Pharmacology
IndicationFor the treatment of depression (originally intended to treat tuberculosis).
PharmacodynamicsIproniazid is a monoamine oxidase inhibitor (MAOI) that was developed as the first anti-depressant.
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9929
Blood Brain Barrier + 0.9799
Caco-2 permeable + 0.6657
P-glycoprotein substrate Non-substrate 0.7484
P-glycoprotein inhibitor I Non-inhibitor 0.9191
P-glycoprotein inhibitor II Non-inhibitor 0.9932
Renal organic cation transporter Non-inhibitor 0.9166
CYP450 2C9 substrate Non-substrate 0.8608
CYP450 2D6 substrate Non-substrate 0.873
CYP450 3A4 substrate Non-substrate 0.614
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9316
CYP450 2D6 substrate Non-inhibitor 0.9522
CYP450 2C19 substrate Non-inhibitor 0.9293
CYP450 3A4 substrate Non-inhibitor 0.7165
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9221
Ames test Non AMES toxic 0.5653
Carcinogenicity Non-carcinogens 0.7081
Biodegradation Not ready biodegradable 0.9893
Rat acute toxicity 2.6600 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9869
hERG inhibition (predictor II) Non-inhibitor 0.943
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point161-161.5U.S. Patent 2,685,585.
logP0.37HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility6.74e-01 g/lALOGPS
logP0.02ALOGPS
logP0.31ChemAxon
logS-2.4ALOGPS
pKa (strongest acidic)13.66ChemAxon
pKa (strongest basic)3.82ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area54.02ChemAxon
rotatable bond count3ChemAxon
refractivity60.96ChemAxon
polarizability19.19ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,685,585.

General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD02579
KEGG CompoundC11777
PubChem Compound3748
PubChem Substance46505059
ChemSpider3617
BindingDB29136
WikipediaIproniazid
ATC CodesN06AF05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Amine oxidase [flavin-containing] B

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details
Comments
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Drug created on September 11, 2007 14:12 / Updated on May 02, 2014 13:46