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Identification
NameNicotinamide
Accession NumberDB02701  (EXPT02307)
Typesmall molecule
Groupsexperimental
Description

An important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and pellagra. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number98-92-0
WeightAverage: 122.1246
Monoisotopic: 122.048012824
Chemical FormulaC6H6N2O
InChI KeyInChIKey=DFPAKSUCGFBDDF-UHFFFAOYSA-N
InChI
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
IUPAC Name
pyridine-3-carboxamide
SMILES
NC(=O)C1=CC=CN=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassPyridinecarboxylic Acids and Derivatives
Direct parentNicotinamides
Alternative parentsPrimary Carboxylic Acid Amides; Polyamines; Enolates; Carboxylic Acids
Substituentscarboxamide group; primary carboxylic acid amide; carboxylic acid derivative; polyamine; enolate; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Nicotinate and Nicotinamide MetabolismMetabolicSMP00048
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9831
Blood Brain Barrier + 0.9911
Caco-2 permeable + 0.8077
P-glycoprotein substrate Non-substrate 0.8778
P-glycoprotein inhibitor I Non-inhibitor 0.9816
P-glycoprotein inhibitor II Non-inhibitor 0.9955
Renal organic cation transporter Non-inhibitor 0.8727
CYP450 2C9 substrate Non-substrate 0.8702
CYP450 2D6 substrate Non-substrate 0.8913
CYP450 3A4 substrate Non-substrate 0.7653
CYP450 1A2 substrate Non-inhibitor 0.832
CYP450 2C9 substrate Non-inhibitor 0.9339
CYP450 2D6 substrate Non-inhibitor 0.9399
CYP450 2C19 substrate Non-inhibitor 0.9523
CYP450 3A4 substrate Non-inhibitor 0.9274
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.943
Ames test Non AMES toxic 0.9483
Carcinogenicity Non-carcinogens 0.9097
Biodegradation Not ready biodegradable 0.7807
Rat acute toxicity 1.5739 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9947
hERG inhibition (predictor II) Non-inhibitor 0.9581
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point130 °CPhysProp
boiling point157 °C at 5.00E-04 mm HgPhysProp
water solubility5E+005 mg/L (at 25 °C)MERCK INDEX (1996)
logP-0.37HANSCH,C ET AL. (1995)
logS0.61ADME Research, USCD
pKa3.35 (at 20 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
water solubility5.01e+01 g/lALOGPS
logP-0.45ALOGPS
logP-0.39ChemAxon
logS-0.39ALOGPS
pKa (strongest acidic)13.39ChemAxon
pKa (strongest basic)3.63ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area55.98ChemAxon
rotatable bond count1ChemAxon
refractivity32.98ChemAxon
polarizability11.71ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

Helmut Beschke, Heinz Friedrich, Klaus-Peter Muller, Gerd Schreyer, “Process for the production of nicotinamide.” U.S. Patent US4314064, issued May, 1949.

US4314064
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00036
KEGG CompoundC00153
PubChem Compound936
PubChem Substance46507386
ChemSpider911
BindingDB27507
ChEBI17154
ChEMBL
Therapeutic Targets DatabaseDAP001410
HETNCA
Drug Product Database39853
Drugs.comhttp://www.drugs.com/cdi/niacinamide-gel.html
WikipediaNicotinamide
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Exotoxin A

Kind: protein

Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)

Pharmacological action: unknown

Components

Name UniProt ID Details
Exotoxin A P11439 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. L-lactate dehydrogenase A chain

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
L-lactate dehydrogenase A chain P00338 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Poly [ADP-ribose] polymerase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Poly [ADP-ribose] polymerase 1 P09874 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. NAD-dependent protein deacylase sirtuin-5, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
NAD-dependent protein deacylase sirtuin-5, mitochondrial Q9NXA8 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. ADP-ribosyl cyclase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
ADP-ribosyl cyclase 2 Q10588 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18