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Identification
NameNialamide
Accession NumberDB04820
TypeSmall Molecule
GroupsWithdrawn
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Withdrawn from the Canadian, US, and UK markets in 1963 due to interactions with food products containing tyrosine.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
1-[2-(Benzylcarbamoyl)ethyl]-2-isonicotinoylhydrazine
2-(2-(Benzylcarbamoyl)ethyl)hydrazide isonicotinic acid
2-(2-(Benzylcarbamoyl)ethyl)hydrazide, isonicotinic acid
2-(2-(Benzylcarbamyl)ethyl)hydrazide isonicotinic acid
2-[2-(Benzylcarbamoyl)ethyl]hydrazide isonicotinic acid
BEIH
Isonicitinic acid 2-[(2-benzylcarbamoyl)ethyl]hydrazide
Isonicotinic acid 2-((2-benzylcarbamoyl)ethyl)hydrazide
Isonicotinic acid, {2-[2-(benzylcarbamoyl)ethyl]hydrazide}
Isonicotinic acid, {2-[2-(benzylcarbamoylethyl]hydrazide}
Isonicotinic acid, 2-(2-(benzylcarbamoyl)ethyl)hydrazide
Isonicotinic acid, 2-[2- (benzylcarbamoyl)ethyl]hydrazide
Isonicotinic acid, 2-[2-(benzylcarbamoyl)ethyl]hydrazide
Isonicotinic acid, 2-[2-(benzylcarbamoylethyl]hydrazide
N-(2-(Benzylcarbamyl)ethylamino)isonicotinamide
N-Benzyl-3-(2-isonicotinoylhydrazino)propanamide
N-benzyl-beta-(isonicotinoylhydrazine)propionamide
N-benzyl-beta-(isonicotinylhydrazino)propionamide
N-isonicotinoyl-n'(beta-n-benzylcarboxamidoethyl)hydrazine
N-isonicotinyl hydrazide
Nialamida
Nialamidum
Pyridine-4-carboxylic 2-[2-(benzylcarbamoyl)ethyl]hydrazide
External Identifiers
  • Lopac-N-1392
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DelmoneurinaNot Available
EsprilNot Available
IsalizinaNot Available
MygalNot Available
NF-xIIINot Available
NialamidNot Available
NiamidNot Available
NiamidalNot Available
NiamideNot Available
NiaquitilNot Available
NiazinNot Available
NovazidNot Available
NuredalNot Available
NyazinNot Available
NyezinNot Available
PsicodistenNot Available
SurgexNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIT2Q0RYM725
CAS number51-12-7
WeightAverage: 298.3397
Monoisotopic: 298.14297584
Chemical FormulaC16H18N4O2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Phenylmethylamine
  • Benzylamine
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxylic acid hydrazide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNialamide was one of the first MAOI (monoamine oxidase inhibitor) antidepressants. It is chemically related to iproniazide, another MAOI derived from isonicotinic acid. //
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+0.9828
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point151.6 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.64 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesN06AF02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
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-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
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 ]
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Drug created on September 11, 2007 14:20 / Updated on September 16, 2013 17:25