NAV

N-methylnicotinamide

Identification

Generic Name
N-methylnicotinamide
DrugBank Accession Number
DB08840
Background

N-methylnicotinamide is an experimental drug with no approved indication or marketed formulation. It is a metabolite of niacinamide/nicotinamide and niacin/nicotinic acid (vitamin B3), and as such N-methylnicotinamide is used to diagnose niacin deficiency by measuring N-methylnicotinamide in the urine.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 136.1512
Monoisotopic: 136.063662888
Chemical Formula
C7H8N2O
Synonyms
  • 3-(Methylcarbamoyl)pyridine
  • 3-(N-Methylcarbamoyl)pyridine
  • N-Methyl nicotineamide
  • N-Methyl-3-pyridinecarboxamide
  • N-methylpyridine-3-carboxamide
  • Nicotinic acid methylamide
  • Nicotinyl methylamide
External IDs
  • NSC-66521
  • SR-4415
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Pharmacology

Indication

N-methylnicotinamide is an experimental drug with no approved indication.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

N-methylnicotinamide is excreted in the urine.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAbacavir may decrease the excretion rate of N-methylnicotinamide which could result in a higher serum level.
AbemaciclibThe excretion of Abemaciclib can be decreased when combined with N-methylnicotinamide.
AceclofenacAceclofenac may decrease the excretion rate of N-methylnicotinamide which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of N-methylnicotinamide which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of N-methylnicotinamide which could result in a higher serum level.
Food Interactions
Not Available

Categories

ATC Codes
A05AB01 — Nicotinyl methylamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridinecarboxylic acids and derivatives
Direct Parent
Nicotinamides
Alternative Parents
Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Nicotinamide / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinecarboxamide (CHEBI:64399)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
X3I82S5L8I
CAS number
114-33-0
InChI Key
ZYVXHFWBYUDDBM-UHFFFAOYSA-N
InChI
InChI=1S/C7H8N2O/c1-8-7(10)6-3-2-4-9-5-6/h2-5H,1H3,(H,8,10)
IUPAC Name
N-methylpyridine-3-carboxamide
SMILES
CNC(=O)C1=CC=CN=C1

References

General References
Not Available
Human Metabolome Database
HMDB0003152
ChemSpider
58476
BindingDB
50420177
ChEBI
64399
ChEMBL
CHEMBL11978
ZINC
ZINC000000404444
PDBe Ligand
PJH
Wikipedia
Nicotinyl_methylamide
PDB Entries
6ynp
MSDS
Download (37.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers (HV)1

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)102 - 105 °C or 216 - 221 °FFrom MSDS.
Predicted Properties
PropertyValueSource
Water Solubility18.6 mg/mLALOGPS
logP-0.21ALOGPS
logP-0.17Chemaxon
logS-0.87ALOGPS
pKa (Strongest Acidic)13.75Chemaxon
pKa (Strongest Basic)3.62Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.99 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity37.88 m3·mol-1Chemaxon
Polarizability13.87 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9793
Blood Brain Barrier+0.9892
Caco-2 permeable+0.8039
P-glycoprotein substrateNon-substrate0.8312
P-glycoprotein inhibitor INon-inhibitor0.96
P-glycoprotein inhibitor IINon-inhibitor0.9928
Renal organic cation transporterNon-inhibitor0.8504
CYP450 2C9 substrateNon-substrate0.7839
CYP450 2D6 substrateNon-substrate0.8731
CYP450 3A4 substrateNon-substrate0.6717
CYP450 1A2 substrateNon-inhibitor0.6152
CYP450 2C9 inhibitorNon-inhibitor0.9711
CYP450 2D6 inhibitorNon-inhibitor0.972
CYP450 2C19 inhibitorNon-inhibitor0.9671
CYP450 3A4 inhibitorNon-inhibitor0.8823
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9181
Ames testNon AMES toxic0.965
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.7993
Rat acute toxicity1.7728 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9895
hERG inhibition (predictor II)Non-inhibitor0.9582
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-2900000000-94cc770fe8f431a31a23
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-52cc0474c9532715d413
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-066r-3900000000-241ac32d21314b2a8518
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-0900000000-98c215c9495562c5d309
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-eea0008770565759cae3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-9bae969f8e8938ee621b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-9fa157749144ceca4c15
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-127.8853886
predicted
DarkChem Lite v0.1.0
[M-H]-127.7225886
predicted
DarkChem Lite v0.1.0
[M-H]-124.977936
predicted
DeepCCS 1.0 (2019)
[M+H]+128.6499886
predicted
DarkChem Lite v0.1.0
[M+H]+128.4305886
predicted
DarkChem Lite v0.1.0
[M+H]+128.44186
predicted
DeepCCS 1.0 (2019)
[M+Na]+127.6897886
predicted
DarkChem Lite v0.1.0
[M+Na]+127.5884886
predicted
DarkChem Lite v0.1.0
[M+Na]+137.54266
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Aldehyde oxidase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xanthine dehydrogenase activity
Specific Function
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal...
Gene Name
AOX1
Uniprot ID
Q06278
Uniprot Name
Aldehyde oxidase
Molecular Weight
147916.735 Da
References
  1. Dick RA, Kanne DB, Casida JE: Identification of aldehyde oxidase as the neonicotinoid nitroreductase. Chem Res Toxicol. 2005 Feb;18(2):317-23. [Article]

Transporters

Details1. Solute carrier family 22 member 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [Article]
Details2. Multidrug and toxin extrusion protein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Ito S, Kusuhara H, Kumagai Y, Moriyama Y, Inoue K, Kondo T, Nakayama H, Horita S, Tanabe K, Yuasa H, Sugiyama Y: N-methylnicotinamide is an endogenous probe for evaluation of drug-drug interactions involving multidrug and toxin extrusions (MATE1 and MATE2-K). Clin Pharmacol Ther. 2012 Nov;92(5):635-41. doi: 10.1038/clpt.2012.138. Epub 2012 Oct 10. [Article]
Details3. Multidrug and toxin extrusion protein 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Drug transmembrane transporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name
SLC47A2
Uniprot ID
Q86VL8
Uniprot Name
Multidrug and toxin extrusion protein 2
Molecular Weight
65083.915 Da
References
  1. Ito S, Kusuhara H, Kumagai Y, Moriyama Y, Inoue K, Kondo T, Nakayama H, Horita S, Tanabe K, Yuasa H, Sugiyama Y: N-methylnicotinamide is an endogenous probe for evaluation of drug-drug interactions involving multidrug and toxin extrusions (MATE1 and MATE2-K). Clin Pharmacol Ther. 2012 Nov;92(5):635-41. doi: 10.1038/clpt.2012.138. Epub 2012 Oct 10. [Article]
  2. Bergagnini-Kolev MC, Hebert MF, Easterling TR, Lin YS: Pregnancy Increases the Renal Secretion of N(1)-methylnicotinamide, an Endogenous Probe for Renal Cation Transporters, in Patients Prescribed Metformin. Drug Metab Dispos. 2017 Mar;45(3):325-329. doi: 10.1124/dmd.116.073841. Epub 2017 Jan 9. [Article]

Drug created at February 22, 2013 20:46 / Updated at June 12, 2020 16:52