Identification
- Generic Name
- Iproniazid
- DrugBank Accession Number
- DB04818
- Background
Withdrawn from the Canadian market in July 1964 due to interactions with food products containing tyrosine.
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
Structure for Iproniazid (DB04818)
- Weight
- Average: 179.219
Monoisotopic: 179.105862053 - Chemical Formula
- C9H13N3O
- Synonyms
- Iproniazid
- Iproniazida
- Iproniazide
- Iproniazidum
- External IDs
- P 887
- Ro 2-4572
Pharmacology
- Indication
For the treatment of depression (originally intended to treat tuberculosis).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Iproniazid is a monoamine oxidase inhibitor (MAOI) that was developed as the first anti-depressant.
- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Iproniazid is combined with 1,2-Benzodiazepine. Abaloparatide Iproniazid may increase the orthostatic hypotensive activities of Abaloparatide. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Iproniazid is combined with Abciximab. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Iproniazid. Acarbose Iproniazid may increase the hypoglycemic activities of Acarbose. Acebutolol Iproniazid may increase the hypotensive activities of Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Iproniazid is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Iproniazid is combined with Acemetacin. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Iproniazid. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Iproniazid. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Iproniazid phosphate 8DE00V62TV 305-33-9 YPDVTKJXVHYWFY-UHFFFAOYSA-N - International/Other Brands
- Euphozid / Iprazid / Ipronid (A.F.I.) / Marsilid (Genopharm) / Rivivol (Zambeletti)
Categories
- ATC Codes
- N06AF05 — Iproniazide
- Drug Categories
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Hydrazines
- Isonicotinic Acids
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Monoamine Oxidase Inhibitors
- Monoamine Oxidase Inhibitors, Non-Selective
- Nervous System
- Psychoanaleptics
- Psychotropic Drugs
- Pyridines
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Pyridinecarboxylic acids and derivatives
- Direct Parent
- Pyridinecarboxylic acids and derivatives
- Alternative Parents
- Heteroaromatic compounds / Carboxylic acid hydrazides / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid derivative / Carboxylic acid hydrazide / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- carbohydrazide, pyridines (CHEBI:5958) / a small molecule (IPRONIAZID)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- D892HFI3XA
- CAS number
- 54-92-2
- InChI Key
- 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
References
- Synthesis Reference
U.S. Patent 2,685,585.
- General References
- Not Available
- External Links
- KEGG Drug
- D02579
- KEGG Compound
- C11777
- PubChem Compound
- 3748
- PubChem Substance
- 46505059
- ChemSpider
- 3617
- BindingDB
- 29136
- 5981
- ChEBI
- 5958
- ChEMBL
- CHEMBL92401
- ZINC
- ZINC000000001579
- Wikipedia
- Iproniazid
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 161-161.5 U.S. Patent 2,685,585. logP 0.37 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.674 mg/mL ALOGPS logP 0.02 ALOGPS logP 0.31 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 13.66 Chemaxon pKa (Strongest Basic) 3.82 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 54.02 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 60.96 m3·mol-1 Chemaxon Polarizability 19.19 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9316 CYP450 2D6 inhibitor Non-inhibitor 0.9522 CYP450 2C19 inhibitor Non-inhibitor 0.9293 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Polasek TM, Elliot DJ, Somogyi AA, Gillam EM, Lewis BC, Miners JO: An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84. doi: 10.1111/j.1365-2125.2006.02627.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Polasek TM, Elliot DJ, Somogyi AA, Gillam EM, Lewis BC, Miners JO: An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84. doi: 10.1111/j.1365-2125.2006.02627.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Serotonin binding
- 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...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Fisar Z, Hroudova J, Raboch J: Inhibition of monoamine oxidase activity by antidepressants and mood stabilizers. Neuro Endocrinol Lett. 2010;31(5):645-56. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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...
- Gene Name
- MAOB
- Uniprot ID
- P27338
- Uniprot Name
- Amine oxidase [flavin-containing] B
- Molecular Weight
- 58762.475 Da
References
- Fisar Z, Hroudova J, Raboch J: Inhibition of monoamine oxidase activity by antidepressants and mood stabilizers. Neuro Endocrinol Lett. 2010;31(5):645-56. [Article]
Drug created at September 11, 2007 20:12 / Updated at February 21, 2021 18:51