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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Withdrawn from the Canadian market in July 1964 due to interactions with food products containing tyrosine.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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
IpronidA.F.I.
MarsilidGenopharm
RivivolZambeletti
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. These are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pyridine carboxylic acid or derivatives
  • Heteroaromatic compound
  • Carboxylic acid hydrazide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9929
Blood Brain Barrier+0.9799
Caco-2 permeable+0.6657
P-glycoprotein substrateNon-substrate0.7484
P-glycoprotein inhibitor INon-inhibitor0.9191
P-glycoprotein inhibitor IINon-inhibitor0.9932
Renal organic cation transporterNon-inhibitor0.9166
CYP450 2C9 substrateNon-substrate0.8608
CYP450 2D6 substrateNon-substrate0.873
CYP450 3A4 substrateNon-substrate0.614
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.9316
CYP450 2D6 substrateNon-inhibitor0.9522
CYP450 2C19 substrateNon-inhibitor0.9293
CYP450 3A4 substrateNon-inhibitor0.7165
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9221
Ames testNon AMES toxic0.5653
CarcinogenicityNon-carcinogens0.7081
BiodegradationNot ready biodegradable0.9893
Rat acute toxicity2.6600 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9869
hERG inhibition (predictor II)Non-inhibitor0.943
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 Solubility0.674 mg/mLALOGPS
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 Area54.02 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.96 m3·mol-1ChemAxon
Polarizability19.19 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,685,585.

General ReferenceNot Available
External Links
ATC CodesNot Available
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
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Drug created on September 11, 2007 14:12 / Updated on May 02, 2014 13:46