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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Withdrawn from the Canadian market in July 1964 due to interactions with food products containing tyrosine.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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EuphozidNot Available
IprazidNot Available
IpronidA.F.I.
IproninNot Available
MarsilidGenopharm
RivivolZambeletti
Brand mixturesNot Available
SaltsNot Available
Categories
UNIID892HFI3XA
CAS number54-92-2
WeightAverage: 179.219
Monoisotopic: 179.105862053
Chemical FormulaC9H13N3O
InChI KeyInChIKey=NYMGNSNKLVNMIA-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
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 inhibitorNon-inhibitor0.9316
CYP450 2D6 inhibitorNon-inhibitor0.9522
CYP450 2C19 inhibitorNon-inhibitor0.9293
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 ReferencesNot 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

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular Weight:
58762.475 Da
Comments
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Drug created on September 11, 2007 14:12 / Updated on October 23, 2015 16:28