Nialamide

Identification

Name
Nialamide
Accession Number
DB04820
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1963 due to interactions with food products containing tyrosine.

Structure
Thumb
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
International/Other Brands
Delmoneurina / Espril / Isalizina / Mygal / NF-xIII / Nialamid / Niamid / Niamidal / Niamide / Niaquitil / Niazin / Novazid / Nuredal / Nyazin / Nyezin / Psicodisten / Surgex
Categories
UNII
T2Q0RYM725
CAS number
51-12-7
Weight
Average: 298.3397
Monoisotopic: 298.14297584
Chemical Formula
C16H18N4O2
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-ylformohydrazido)propanamide
SMILES
O=C(CCNNC(=O)C1=CC=NC=C1)NCC1=CC=CC=C1

Pharmacology

Indication
Not Available
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. //

TargetActionsOrganism
UAmine oxidase [flavin-containing] BNot AvailableHuman
UAmine oxidase [flavin-containing] ANot AvailableHuman
UCatechol O-methyltransferaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Nialamide is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Nialamide is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidNialamide may increase the hypotensive activities of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Nialamide.
2,4-thiazolidinedioneNialamide may increase the hypoglycemic activities of 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineNialamide may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineNialamide may increase the hypertensive activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineNialamide may increase the hypertensive activities of 3,4-Methylenedioxyamphetamine.
3,5-DinitrocatecholThe risk or severity of adverse effects can be increased when 3,5-Dinitrocatechol is combined with Nialamide.
4-Bromo-2,5-dimethoxyamphetamineNialamide may increase the hypertensive activities of 4-Bromo-2,5-dimethoxyamphetamine.
Food Interactions
Not Available

References

General References
  1. Benady DR, Clein LJ, Pare CM: Intramuscular nialamide in intractable depression. Dis Nerv Syst. 1965 Dec;26(12):792-4. [PubMed:5321917]
  2. OULES J, CAZABON: [TREATMENT OF DEPRESSIVE STATES WITH INTRAVENOUS NIAMIDE]. Toulouse Med. 1964 Dec;65:1298-302. [PubMed:14272189]
  3. 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. [PubMed:13840714]
External Links
PubChem Compound
4472
PubChem Substance
46506047
ChemSpider
4317
BindingDB
163693
ChEBI
94510
ChEMBL
CHEMBL1256841
Wikipedia
Nialamide
ATC Codes
N06AF02 — Nialamide

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)151.6 °CPhysProp
logP0.87HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0873 mg/mLALOGPS
logP0.65ALOGPS
logP0.39ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.65ChemAxon
pKa (Strongest Basic)3.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.12 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.91 m3·mol-1ChemAxon
Polarizability32.07 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9828
Blood Brain Barrier+0.9382
Caco-2 permeable-0.5586
P-glycoprotein substrateNon-substrate0.589
P-glycoprotein inhibitor IInhibitor0.5514
P-glycoprotein inhibitor IINon-inhibitor0.8207
Renal organic cation transporterNon-inhibitor0.6666
CYP450 2C9 substrateNon-substrate0.8668
CYP450 2D6 substrateNon-substrate0.7826
CYP450 3A4 substrateNon-substrate0.6434
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8818
CYP450 2D6 inhibitorInhibitor0.816
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7334
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7368
BiodegradationNot ready biodegradable0.9791
Rat acute toxicity2.2756 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7944
hERG inhibition (predictor II)Inhibitor0.5599
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.64 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-056u-9500000000-09562bed5beb21b860eb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0981000000-1b525a17732679e11621
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fk9-4900000000-edf91905d0d264f001ea

Taxonomy

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
Pyridine carboxylic acid or derivatives / Monocyclic benzene moiety / Benzenoid / Heteroaromatic compound / Carboxylic acid hydrazide / Azacycle / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboxylic acid derivative / Carboximidic acid derivative
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. 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. [PubMed:2506486]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:2506486]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:1170911]

Drug created on September 11, 2007 14:20 / Updated on December 14, 2018 05:38