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Showing Compound Isoniazid (FDB029229)

Record Information
Version1.0
Creation date2011-09-21 01:52:13 UTC
Update date2015-07-21 06:59:39 UTC
Primary IDFDB029229
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoniazid
DescriptionIsoniazid (also called isonicotinyl hydrazine or INH; sold as Laniazid, Nydrazid) is an organic compound that is the first-line antituberculosis medication in prevention and treatment. First discovered in 1912 as an inhibitor of the MAO enzyme, it was first used as an antidepressant, but discontinued due to side effects. In 1951, it was later discovered that isoniazid was effective against TB. Isoniazid is never used on its own to treat active tuberculosis because resistance quickly develops.; Isoniazid is a bactericidal agent active against organisms of the genus Mycobacterium, specifically M. tuberculosis, M. bovis and M. kansasii. It is a highly specific agent, ineffective against other microorganisms. Isoniazid is bactericidal to rapidly-dividing mycobacteria, but is bacteriostatic if the mycobacterium is slow-growing.; Isoniazid is a prodrug and must be activated by bacterial catalase. It is activated by catalase-peroxidase enzyme KatG which couples the isonicotinic acyl with NADH to form isonicotinic acyl-NADH complex. This complex binds tightly to ketoenoylreductase known as InhA, thereby blocking the natural enoyl-AcpM substrate and the action of fatty acid synthase. This process inhibits the synthesis of mycolic acid required for the mycobacterial cell wall. A range of radicals are produced by KatG activation of Isoniazid, including nitric oxide, that has also been shown to be important in the action of another antimycobacterial prodrug PA824. [HMDB]
CAS Number54-85-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
(HBD) Human beta-defensin-1 & INHhmdb
4-(Hydrazinocarbonyl)pyridinehmdb
4-Pyridinecarbonylhydrazinehmdb
4-Pyridinecarboxylic acid hydrazidehmdb
4-Pyridinecarboxylic acid, hydrazidehmdb
4-Pyridinecarboxylic hydrazidehmdb
4-Pyridylcarbonyl hydrazidehmdb
4-Pyridylcarbonylhydrazidehmdb
Abdizidehmdb
Amidonhmdb
Andrazidehmdb
Anidrasonahmdb
Antimicinahmdb
Antituberkulosumhmdb
Armacidehmdb
Armazidhmdb
Armazidehmdb
Atcotibinehmdb
Azt + isoniazidhmdb
Azurenhmdb
Bacillenhmdb
Bacillinhmdb
Cedinhmdb
Cedin (aerosol)hmdb
Cemidonhmdb
Chemiazidhmdb
Chemidonhmdb
Continazinehmdb
Cortinazinehmdb
Cotinazinhmdb
Cotinizinhmdb
Defoninhmdb
Dibutinhmdb
Diforinhmdb
Dinacrinhmdb
Ditubinhmdb
Dom-Isoniazid 300mg Tabletshmdb
Dow-isoniazidhmdb
Ebidenehmdb
Eralonhmdb
Ertubanhmdb
Eutizonhmdb
Evalonhmdb
Fetefuhmdb
Fimalenehmdb
FRS-3hmdb
FSR 3hmdb
FSR-3hmdb
GINKhmdb
Hid rasonilhmdb
Hidranizilhmdb
Hidrasonilhmdb
Hidrultahmdb
Hidrunhmdb
Hycozidhmdb
Hydrahmdb
Hyozidhmdb
Hyzydhmdb
I.a.Ihmdb
I.a.I.hmdb
I3377_FLUKAhmdb
I3377_SIGMAhmdb
Ido-tebinhmdb
Idrazide dell'acido isonicotinico [italian]hmdb
Idrazilhmdb
INAHhmdb
Inh-burgthalhmdb
INHd20hmdb
Inizidhmdb
Iscotinhmdb
Isidrinahmdb
Ismazidehmdb
Isobicinahmdb
Isocidhmdb
Isocidenehmdb
Isoco tinhmdb
Isocotinhmdb
Isokinhmdb
Isolynhmdb
Isonerithmdb
Isoniacidhmdb
Isoniazid (JP15/USP/INN)hmdb
Isoniazid [ban:inn:jan]hmdb
Isoniazid [inn:ban:jan]hmdb
Isoniazid & CRL8131hmdb
Isoniazid & eephmdb
Isoniazid & propolishmdb
Isoniazid daily for 9 monthshmdb
Isoniazid sahmdb
Isoniazid(isonicotinic acid)hmdb
Isoniazida [inn-spanish]hmdb
Isoniazidehmdb
Isoniazidum [inn-latin]hmdb
Isonicazidehmdb
Isonicidhmdb
Isonicohmdb
Isonicotanhmdb
Isonicotilhmdb
isonicotinohydrazide (ACD/Name 4.0)hmdb
Isonicotinoylhydrazinehmdb
Isonicotinsaeurehydrazid [german]hmdb
Isonicotinylhydrazidehmdb
Isonidehmdb
Isonidrinhmdb
Isonikazidhmdb
Isonilexhmdb
Isoninhmdb
Isonindonhmdb
Isonirithmdb
Isonitonhmdb
Isonizidahmdb
Isonizidehmdb
Isopyrinhmdb
Isotaminehmdb
Isotamine powderhmdb
Isotamine Syr Pediatric 50mg/5mlhmdb
Isotamine-100hmdb
Isotamine-300hmdb
Isotebehmdb
Isotebezidhmdb
Isotinylhmdb
Isozidhmdb
Isozid ehmdb
Isozidehmdb
Isozydhmdb
ISZhmdb
Laniazid (TN)hmdb
Laniozidhmdb
Lanizidhmdb
Mixture namehmdb
Mybasanhmdb
nchembio884-comp3hmdb
Neo-tizidehmdb
Neotebenhmdb
Neoxinhmdb
Neumandinhmdb
Nevinhmdb
Niadrinhmdb
Niazidhmdb
Nicazidehmdb
Nicetalhmdb
Nicizinahmdb
Niconylhmdb
Nicotibinahmdb
Nicotibinehmdb
Nicotisanhmdb
Nicozidehmdb
Nidatonhmdb
Nidra zidhmdb
Nidrazidhmdb
Nikozidhmdb
Niplenhmdb
Nitadonhmdb
Nitebanhmdb
Nitebannsc 9659hmdb
Nydrazidhmdb
Nyscozidhmdb
Pelazidhmdb
Percinhmdb
Phthisenhmdb
Pms-Isoniazid 100mg/Tabhmdb
Pms-Isoniazid 300mg/Tabhmdb
Pms-Isoniazid Syrup 50mg/5mlhmdb
Pms-Isoniazid Tab 50mghmdb
Preparation 6424hmdb
Prestwick_578hmdb
Pycazidehmdb
Pyreazidhmdb
Pyricidinhmdb
Pyridicinhmdb
pyridine-4-carbohydrazidehmdb
Pyrizidinhmdb
Raumanonhmdb
Razidehmdb
Retozidehmdb
Rifamatehmdb
Rifaterhmdb
Rimicidhmdb
Rimif onhmdb
Rimifonhmdb
Rimiphonehmdb
Rimitsidhmdb
Robiselinhmdb
Robisellinhmdb
Roxifenhmdb
Ru-ef-TBhmdb
RY-ef-TBhmdb
Sanohidrazinahmdb
Sauterazidhmdb
Sauterzidhmdb
Stanozidehmdb
TB-phloginhmdb
TB-razidehmdb
TB-vishmdb
Tebecidhmdb
Tebemidhmdb
Tebenichmdb
Tebexinhmdb
Tebilonhmdb
Teboshmdb
Teebaconinhmdb
Tekazinhmdb
Tibazidehmdb
Tibemidhmdb
Tibiazidehmdb
Tibisonhmdb
Tibivishmdb
Tibusanhmdb
Tubazidhmdb
Tubecohmdb
Tubecotubercidhmdb
Tubercidhmdb
Tuberianhmdb
Tubiconhmdb
Tubilysinhmdb
Tubizidhmdb
Tubomelhmdb
Tyvidhmdb
Unicocydehmdb
Unicozydehmdb
Usaf cb-2hmdb
Vazadrinehmdb
Vederonhmdb
WLN: T6NJ DVMZhmdb
Zidafimiahmdb
Zinadonhmdb
Zonazidehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H7N3O
IUPAC namepyridine-4-carbohydrazide
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
Isomeric SMILESNNC(=O)C1=CC=NC=C1
Average Molecular Weight137.1393
Monoisotopic Molecular Weight137.058911861
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0kdr-9600000000-f04526999a9b68d318612014-09-20View Spectrum
Predicted GC-MSIsoniazid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-2900000000-d379ce585203e68cb06aSpectrum
Predicted GC-MSIsoniazid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-3cf8f43d0df46334dcd92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-7900000000-3d43394feacded48669d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-263a0bcadf2e215369832017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002f-9000000000-17100430370d37f834ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9466b9291244c1a61f012017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-afcf227eec118bec08a42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-1900000000-d63af1f463124dbf7b652017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00fr-9600000000-1d50dedb0eea7ff8dccb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-371fd6d67c48f373e2e52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-dee0012ebd004444b3d82017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-2900848c5042f3badc642016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-aeda0fc92729a25612482016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9200000000-8cdf3d4be1d99712a8392016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-0de7d57696bde8b4ad722016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-4900000000-8760bef4d7b9a5b3360c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9100000000-7dfda590da30abf9e3292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-37604552ea11c4e9ae142021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-0fe0a0315394b81d8b4e2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9100000000-3169da9068df634af7d42021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-7900000000-1e1d0995890b4dca17722021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-c2850ce6846335b0374d2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fdff89cf4c9b7fb7a6532021-10-11View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC07054
Pubchem Compound ID3767
Pubchem Substance IDNot Available
ChEBI ID6030
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12982
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDisoniazid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference