Identification
- Generic Name
- Nialamide
- DrugBank Accession Number
- DB04820
- Background
Withdrawn from the Canadian, US, and UK markets in 1963 due to interactions with food products containing tyrosine.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Nialamide (DB04820)
- Weight
- Average: 298.3397
Monoisotopic: 298.14297584 - Chemical Formula
- C16H18N4O2
- Synonyms
- 1-(2-(Benzylcarbamoyl)ethyl)-2-isonicotinoylhydrazine
- 2-(2-(Benzylcarbamoyl)ethyl)hydrazide isonicotinic acid
- 2-(2-(Benzylcarbamyl)ethyl)hydrazide isonicotinic acid
- BEIH
- Isonicotinic acid 2-((2-benzylcarbamoyl)ethyl)hydrazide
- Isonicotinic acid, 2-(2-(benzylcarbamoyl)ethyl)hydrazide
- N-(2-(Benzylcarbamyl)ethylamino)isonicotinamide
- N-benzyl-beta-(isonicotinoylhydrazine)propionamide
- N-benzyl-beta-(isonicotinylhydrazino)propionamide
- N-Isonicotinoyl-N'(beta-N-benzylcarboxamidoethyl)hydrazine
- Nialamida
- Nialamide
- Nialamidum
- External IDs
- Lopac-N-1392
Pharmacology
- Indication
Not Available
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
Not Available
- Mechanism of action
Nialamide was one of the first MAOI (monoamine oxidase inhibitor) antidepressants. It is chemically related to iproniazide, another MAOI derived from isonicotinic acid. //
Target Actions Organism UAmine oxidase [flavin-containing] B Not Available Humans UAmine oxidase [flavin-containing] A Not Available Humans UCatechol O-methyltransferase Not Available Humans - 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 Nialamide is combined with 1,2-Benzodiazepine. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Nialamide is combined with Abciximab. Acarbose Nialamide may increase the hypoglycemic activities of Acarbose. Acebutolol Nialamide may increase the hypotensive activities of Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Nialamide is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Nialamide is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Nialamide is combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Nialamide. Acetohexamide Nialamide may increase the hypoglycemic activities of Acetohexamide. Acetophenazine The risk or severity of extrapyramidal symptoms can be increased when Nialamide is combined with Acetophenazine. 
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.- International/Other Brands
- Delmoneurina / Niamid / Niamide / Nuredal / Surgex
Categories
- ATC Codes
- N06AF02 — Nialamide
- Drug Categories
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Enzyme Inhibitors
- Isonicotinic Acids
- 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
- Benzene and substituted derivatives / Heteroaromatic compounds / Carboxylic acid hydrazides / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid derivative / Carboxylic acid hydrazide / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety show 9 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- T2Q0RYM725
- CAS number
- 51-12-7
- InChI Key
- NOIIUHRQUVNIDD-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H18N4O2/c21-15(18-12-13-4-2-1-3-5-13)8-11-19-20-16(22)14-6-9-17-10-7-14/h1-7,9-10,19H,8,11-12H2,(H,18,21)(H,20,22)
- IUPAC Name
- N-benzyl-3-[(pyridin-4-yl)formohydrazido]propanamide
- SMILES
- O=C(CCNNC(=O)C1=CC=NC=C1)NCC1=CC=CC=C1
References
- General References
- Benady DR, Clein LJ, Pare CM: Intramuscular nialamide in intractable depression. Dis Nerv Syst. 1965 Dec;26(12):792-4. [Article]
- OULES J, CAZABON: [TREATMENT OF DEPRESSIVE STATES WITH INTRAVENOUS NIAMIDE]. Toulouse Med. 1964 Dec;65:1298-302. [Article]
- VAISBERG M, McGAHEE CL, RADINGER N, SAUNDERS JC: Nialamide for the treatment of anergy and depression. Dis Nerv Syst. 1959 Aug;20(Suppl):22-5. [Article]
- External Links
- PubChem Compound
- 4472
- PubChem Substance
- 46506047
- ChemSpider
- 4317
- BindingDB
- 163693
- 7394
- ChEBI
- 94510
- ChEMBL
- CHEMBL1256841
- ZINC
- ZINC000001713761
- Wikipedia
- Nialamide
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) 151.6 °C PhysProp logP 0.87 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0873 mg/mL ALOGPS logP 0.65 ALOGPS logP 0.39 ChemAxon logS -3.5 ALOGPS pKa (Strongest Acidic) 13.65 ChemAxon pKa (Strongest Basic) 3.41 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 83.12 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 93.91 m3·mol-1 ChemAxon Polarizability 32.07 Å3 ChemAxon Number of Rings 2 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 + 0.9828 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.5586 P-glycoprotein substrate Non-substrate 0.589 P-glycoprotein inhibitor I Inhibitor 0.5514 P-glycoprotein inhibitor II Non-inhibitor 0.8207 Renal organic cation transporter Non-inhibitor 0.6666 CYP450 2C9 substrate Non-substrate 0.8668 CYP450 2D6 substrate Non-substrate 0.7826 CYP450 3A4 substrate Non-substrate 0.6434 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Inhibitor 0.8818 CYP450 2D6 inhibitor Inhibitor 0.816 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7334 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.7368 Biodegradation Not ready biodegradable 0.9791 Rat acute toxicity 2.2756 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7944 hERG inhibition (predictor II) Inhibitor 0.5599
Spectra
- Mass Spec (NIST)
- Download (8.64 KB)
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - EI-B GC-MS splash10-056u-9500000000-09562bed5beb21b860eb 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 LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0002-0981000000-1b525a17732679e11621 MS/MS Spectrum - , positive LC-MS/MS splash10-0fk9-4900000000-edf91905d0d264f001ea
Targets
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- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- MAOB
- Uniprot ID
- P27338
- Uniprot Name
- Amine oxidase [flavin-containing] B
- Molecular Weight
- 58762.475 Da
References
- Hovevey-Sion D, Kopin IJ, Stull RW, Goldstein DS: Effects of monoamine oxidase inhibitors on levels of catechols and homovanillic acid in striatum and plasma. Neuropharmacology. 1989 Aug;28(8):791-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Hovevey-Sion D, Kopin IJ, Stull RW, Goldstein DS: Effects of monoamine oxidase inhibitors on levels of catechols and homovanillic acid in striatum and plasma. Neuropharmacology. 1989 Aug;28(8):791-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- O-methyltransferase activity
- Specific Function
- Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
- Gene Name
- COMT
- Uniprot ID
- P21964
- Uniprot Name
- Catechol O-methyltransferase
- Molecular Weight
- 30036.77 Da
References
- Parvez S, Parvez SH, Youdim MB: Variation in activity of monoamine metabolizing enzymes in rat liver during pregnancy. Br J Pharmacol. 1975 Feb;53(2):241-6. [Article]
Drug created at September 11, 2007 20:20 / Updated at February 21, 2021 18:51