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Record Information
Version1.0
Creation Date2014-09-11 05:16:08 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003734
Identification
Common NameIsoniazid
ClassSmall Molecule
DescriptionAntibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Antitubercular Agent
  • Drug
  • Ester
  • Fatty Acid Synthesis Inhibitor
  • Food Toxin
  • Hydrazine
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
4-PyridinecarbohydrazideChEBI
Isonicotinic acid hydrazideChEBI
Isonicotinic hydrazideChEBI
IsonicotinohydrazideChEBI
IsonicotinoylhydrazideChEBI
IsonicotinsaeurehydrazidChEBI
Pyridine-4-carboxylic acid hydrazideChEBI
LaniazidKegg
Isonicotinate hydrazideGenerator
Pyridine-4-carboxylate hydrazideGenerator
HIAHMDB
HydrazidHMDB
HydrazideHMDB
INHHMDB
IsohydrazideHMDB
IsonicotinhydrazidHMDB
Isonicotinoyl hydrazideHMDB
Isonicotinyl hydrazideHMDB
Isonicotinyl hydrazineHMDB
IsonicotinylhydrazineHMDB
Hydrazide, isonicotinic acidHMDB
IsonexHMDB
TubazideHMDB
Vanillylidenehydrazide, isonicotinic acidHMDB
Acid vanillylidenehydrazide, isonicotinicHMDB
Isonicotinic acid vanillylidenehydrazideHMDB
FtivazideHMDB
PhthivazideHMDB
PhthivazidHMDB
IsoniazidChEBI
Chemical FormulaC6H7N3O
Average Molecular Mass137.139 g/mol
Monoisotopic Mass137.059 g/mol
CAS Registry Number54-85-3
IUPAC Namepyridine-4-carbohydrazide
Traditional Nameisoniazid
SMILESNNC(=O)C1=CC=NC=C1
InChI IdentifierInChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)
InChI KeyQRXWMOHMRWLFEY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pyridine carboxylic acid or derivatives
  • Heteroaromatic compound
  • Carboxylic acid hydrazide
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point171.4°C
Boiling PointNot Available
Solubility1.4E+005 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility34.9 g/LALOGPS
logP-0.71ALOGPS
logP-0.69ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)3.35ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.01 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.46 m³·mol⁻¹ChemAxon
Polarizability13.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0a4i-2900000000-d379ce585203e68cb06aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-3cf8f43d0df46334dcd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-7900000000-3d43394feacded48669dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-263a0bcadf2e21536983View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002f-9000000000-17100430370d37f834ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9466b9291244c1a61f01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-afcf227eec118bec08a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-1900000000-d63af1f463124dbf7b65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00fr-9600000000-1d50dedb0eea7ff8dccbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-371fd6d67c48f373e2e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-dee0012ebd004444b3d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-2900848c5042f3badc64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-aeda0fc92729a2561248View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9200000000-8cdf3d4be1d99712a839View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-0de7d57696bde8b4ad72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4900000000-8760bef4d7b9a5b3360cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9100000000-7dfda590da30abf9e329View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0kdr-9600000000-f04526999a9b68d31861View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureReadily absorbed following oral administration; however, may undergo significant first pass metabolism. Absorption and bioavailability are reduced when isoniazid is administered with food.
Mechanism of ToxicityIsoniazid is a prodrug and must be activated by bacterial catalase. Specficially, activation is associated with reduction of the mycobacterial ferric KatG catalase-peroxidase by hydrazine and reaction with oxygen to form an oxyferrous enzyme complex. Once activated, isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. At therapeutic levels isoniazid is bacteriocidal against actively growing intracellular and extracellular Mycobacterium tuberculosis organisms. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA.
MetabolismPrimarily hepatic. Isoniazid is acetylated by N -acetyl transferase to N -acetylisoniazid; it is then biotransformed to isonicotinic acid and monoacetylhydrazine. Monoacetylhydrazine is associated with hepatotoxicity via formation of a reactive intermediate metabolite when N-hydroxylated by the cytochrome P450 mixed oxidase system. The rate of acetylation is genetically determined. Slow acetylators are characterized by a relative lack of hepatic N -acetyltransferase. Route of Elimination: From 50 to 70 percent of a dose of isoniazid is excreted in the urine within 24 hours. Half Life: Fast acetylators: 0.5 to 1.6 hours. Slow acetylators: 2 to 5 hours.
Toxicity ValuesLD50 100 mg/kg (Human, oral).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesFor the treatment of all forms of tuberculosis in which organisms are susceptible.
Minimum Risk LevelNot Available
Health Effects Adverse reactions include rash, abnormal liver function tests, hepatitis, peripheral neuropathy, mild central nervous system (CNS) effects. In vivo, Isoniazid reacts with pyridoxal to form a hydrazone, and thus inhibits generation of pyridoxal phosphate. Isoniazid also combines with pyridoxal phosphate; high doses interfere with the coenzyme function of the latter.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00951
HMDB IDHMDB0015086
FooDB IDFDB029229
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDISONIAZIDE
METLIN IDNot Available
PDB IDNIZ
Wikipedia LinkIsoniazid
Chemspider ID3635
ChEBI ID6030
PubChem Compound ID3767
Kegg Compound IDC07054
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Costin Rentzea, Albrecht Harreus, Eberhard Ammermann, Gisela Lorenz, “Oxalyl hydrazide-hydroxamic acid derivatives, their preparation and their use as fungicides.” U.S. Patent US5399589, issued November, 1969.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15013786
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18220565
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19183459
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=445303