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Identification
NameIsoniazid
Accession NumberDB00951  (APRD01055, EXPT01940)
TypeSmall Molecule
GroupsApproved
Description

Antibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis. [PubChem]

Structure
Thumb
Synonyms
4-pyridinecarbohydrazide
INH
Isoniazid
Isonicotinic acid hydrazide
Isonicotinic hydrazide
Isonicotinohydrazide
Isonicotinoylhydrazide
Isonicotinsaeurehydrazid
Isonicotinylhydrazine
Pyridine-4-carboxylic acid hydrazide
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-isoniazid 300mg Tabletstablet300 mgoralDominion Pharmacal1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isoniazidtablet300 mg/1oralEon Labs, Inc.1978-12-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralPreferred Pharmaceuticals Inc.2015-10-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralREMEDYREPACK INC.2013-05-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralREMEDYREPACK INC.2011-12-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralREMEDYREPACK INC.2011-07-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralREMEDYREPACK INC.2011-06-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralEon Labs, Inc.1978-12-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazid Syrup 50mg/5mlsyrup50 mgoralCarolina Medical Products Company1987-12-311999-07-26Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isoniazid Tab 100mgtablet100 mgoralSands Pharm1980-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isoniazid Tab 300mgtablet300 mgoralSands Pharm1974-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isoniazid Tab 50mgtablet50 mgoralSands Pharm1976-12-311996-09-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isoniazide 100mg Tabletstablet100 mgoralLaboratoires Confab IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isotamine Powderpowder500 goralValeant Canada Lp Valeant Canada S.E.C.1976-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isotamine Syr Pediatric 50mg/5mlsyrup10 mgoralValeant Canada Lp Valeant Canada S.E.C.1977-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isotamine-100tablet100 mgoralValeant Canada Lp Valeant Canada S.E.C.1972-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Isotamine-300tablet300 mgoralValeant Canada Lp Valeant Canada S.E.C.1972-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pdp-isoniazidsolution50 mgoralPendopharm Division Of De Pharmascience Inc1984-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pdp-isoniazidtablet300 mgoralPendopharm Division Of De Pharmascience Inc1984-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pdp-isoniazidtablet100 mgoralPendopharm Division Of De Pharmascience Inc1984-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Pdp-isoniazidtablet50 mgoralPendopharm Division Of De Pharmascience Inc1986-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Isoniazidtablet300 mg/1oralClinical Solutions Wholesale1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidsyrup50 mg/5mLoralMikart, Inc.1997-07-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralWest Ward Pharmaceuticals Corp1972-02-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralNorthwind Pharmaceuticals, LLC2014-07-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidinjection, solution100 mg/mLintramuscularSandoz Inc2006-01-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralPreferred Pharmaceuticals, Inc.2004-08-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralPhysicians Total Care, Inc.1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralREMEDYREPACK INC.2014-06-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralMylan Institutional Inc.1994-06-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralBarr Laboratories Inc.1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralContract Pharmacy Services Pa2010-08-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralA S Medication Solutions Llc1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralRebel Distributors Corp1981-07-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralREMEDYREPACK INC.2013-03-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralBarr Laboratories Inc.1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralbryant ranch prepack1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidsolution50 mg/5mLoralA S Medication Solutions Llc1983-11-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralSTAT Rx USA LLC2010-10-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralREMEDYREPACK INC.2011-09-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oral; oralLannett Company, Inc.2013-10-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralbryant ranch prepack1981-07-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralA S Medication Solutions Llc1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralBlenheim Pharmacal, Inc.2010-03-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralREMEDYREPACK INC.2011-09-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralLiberty Pharmaceuticals, Inc.1981-07-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidsolution50 mg/5mLoralbryant ranch prepack1983-11-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralBlenheim Pharmacal, Inc.2013-06-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralMikart, Inc.1997-06-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralLiberty Pharmaceuticals, Inc.1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralVersa Pharm Incorporated1997-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oral; oralAmerican Health Packaging2013-10-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralH.J. Harkins Company, Inc.1981-07-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralBlenheim Pharmacal, Inc.2012-09-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralClinical Solutions Wholesale1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidsolution50 mg/5mLoralCarolina Medical Products Company1983-11-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralVersa Pharm Incorporated1997-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralMikart, Inc.1997-06-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralWest Ward Pharmaceuticals Corp1981-07-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralREMEDYREPACK INC.2014-05-27Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralMajor Pharmaceuticals1972-02-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralPreferred Pharmaceuticals, Inc.2014-11-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet100 mg/1oralPd Rx Pharmaceuticals, Inc.1972-02-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Isoniazidtablet300 mg/1oralPd Rx Pharmaceuticals, Inc.1972-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
NicozidPiam
NidrazidZentiva
NydrazidSandoz
RimicidSopharma
RimifonRoche
ServizidNovartis
TibinideMeda
Brand mixtures
NameLabellerIngredients
IsonarifVersa Pharm Incorporated
Isotamine B 300Valeant Canada Lp Valeant Canada S.E.C.
RifamateSanofi Aventis U.S. Llc
RifaterSanofi Aventis U.S. Llc
SaltsNot Available
Categories
UNIIV83O1VOZ8L
CAS number54-85-3
WeightAverage: 137.1393
Monoisotopic: 137.058911861
Chemical FormulaC6H7N3O
InChI KeyInChIKey=QRXWMOHMRWLFEY-UHFFFAOYSA-N
InChI
InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)
IUPAC Name
pyridine-4-carbohydrazide
SMILES
NNC(=O)C1=CC=NC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. These 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
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of all forms of tuberculosis in which organisms are susceptible.
PharmacodynamicsIsoniazid 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.
Mechanism of actionIsoniazid 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.
AbsorptionReadily absorbed following oral administration; however, may undergo significant first pass metabolism. Absorption and bioavailability are reduced when isoniazid is administered with food.
Volume of distributionNot Available
Protein bindingVery low (0-10%)
Metabolism

Primarily 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 eliminationFrom 50 to 70 percent of a dose of isoniazid is excreted in the urine within 24 hours.
Half lifeFast acetylators: 0.5 to 1.6 hours. Slow acetylators: 2 to 5 hours.
ClearanceNot Available
ToxicityLD50 100 mg/kg (Human, oral). 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.
Affected organisms
  • Mycobacteria
  • Mycobacterium tuberculosis
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
Cytochrome P450 2E1
Gene symbol: CYP2E1
UniProt: P05181
rs6413419 CYP2E1 *1AG Allele, homozygoteHepatotoxicity16770646
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9892
Blood Brain Barrier+0.9895
Caco-2 permeable+0.6959
P-glycoprotein substrateNon-substrate0.8315
P-glycoprotein inhibitor INon-inhibitor0.9778
P-glycoprotein inhibitor IINon-inhibitor0.996
Renal organic cation transporterNon-inhibitor0.9054
CYP450 2C9 substrateNon-substrate0.9088
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7557
CYP450 1A2 substrateInhibitor0.6482
CYP450 2C9 inhibitorNon-inhibitor0.9273
CYP450 2D6 inhibitorNon-inhibitor0.9443
CYP450 2C19 inhibitorNon-inhibitor0.9513
CYP450 3A4 inhibitorNon-inhibitor0.5111
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9342
Ames testAMES toxic0.8557
CarcinogenicityNon-carcinogens0.7514
BiodegradationNot ready biodegradable0.981
Rat acute toxicity2.0713 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9872
hERG inhibition (predictor II)Non-inhibitor0.9586
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sandoz canada inc
  • Sandoz inc
  • Hoffmann la roche inc
  • Carolina medical products co
  • Mikart inc
  • Lannett co inc
  • Dow pharmaceutical corp sub dow chemical co
  • Medpointe pharmaceuticals medpointe healthcare inc
  • Novartis pharmaceuticals corp
  • Barr laboratories inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Halsey drug co inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Eli lilly and co
  • Mk laboratories inc
  • Mutual pharmaceutical co inc
  • Nexgen pharma inc
  • Panray corp sub ormont drug and chemical co inc
  • L perrigo co
  • Pharmavite pharmaceuticals
  • Phoenix laboratories inc
  • Purepac pharmaceutical co
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Whiteworth towne paulsen inc
  • Bristol myers squibb co
  • Everylife
Packagers
Dosage forms
FormRouteStrength
Tabletoral300 mg
Injection, solutionintramuscular100 mg/mL
Solutionoral50 mg/5mL
Syruporal50 mg/5mL
Tabletoral100 mg/1
Tabletoral300 mg/1
Tabletoral; oral300 mg/1
Syruporal50 mg
Tabletoral
Powderoral500 g
Syruporal10 mg
Tabletoral100 mg
Solutionoral50 mg
Tabletoral50 mg
Capsuleoral
Tablet, sugar coatedoral
Prices
Unit descriptionCostUnit
Isoniazid 100 mg/ml vial27.37USD ml
Rifamate 150-300 mg capsule4.36USD capsule
Rifamate capsule4.19USD capsule
Isoniazid 100 mg tablet0.28USD tablet
Isoniazid 300 mg tablet0.18USD tablet
Isoniazid 50 mg/5ml Syrup0.16USD ml
Isoniazid powder0.11USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point171.4 °CPhysProp
water solubility1.4E+005 mg/L (at 25 °C)MERCK INDEX (2001)
logP-0.70HANSCH,C ET AL. (1995)
logS0.01ADME Research, USCD
pKa1.82 (at 20 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility34.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.46 m3·mol-1ChemAxon
Polarizability13.21 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.21 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-zq00000000-f04526999a9b68d31861View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot 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.

US5399589
General ReferencesNot Available
External Links
ATC CodesJ04AC01
AHFS Codes
  • 08:16.04
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.1 KB)
Interactions
Drug Interactions
Drug
AcetaminophenThe risk or severity of adverse effects can be increased when Isoniazid is combined with Acetaminophen.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Isoniazid resulting in a reduced serum concentration and potentially a decrease in efficacy.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Isoniazid.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Isoniazid.
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Isoniazid resulting in a loss in efficacy.
BetamethasoneThe serum concentration of Isoniazid can be decreased when it is combined with Betamethasone.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Isoniazid.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Isoniazid.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Isoniazid resulting in a reduced serum concentration and potentially a decrease in efficacy.
CarbamazepineThe metabolism of Carbamazepine can be decreased when combined with Isoniazid.
ChlorzoxazoneThe metabolism of Chlorzoxazone can be decreased when combined with Isoniazid.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Isoniazid.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Isoniazid.
ClopidogrelThe serum concentration of the active metabolites of Clopidogrel can be reduced when Clopidogrel is used in combination with Isoniazid resulting in a loss in efficacy.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Isoniazid.
CorticotropinThe serum concentration of Isoniazid can be decreased when it is combined with Corticotropin.
Cortisone acetateThe serum concentration of Isoniazid can be decreased when it is combined with Cortisone acetate.
CycloserineThe risk or severity of adverse effects can be increased when Isoniazid is combined with Cycloserine.
Cyproterone acetateThe serum concentration of Isoniazid can be decreased when it is combined with Cyproterone acetate.
DacarbazineThe metabolism of Dacarbazine can be decreased when combined with Isoniazid.
DexamethasoneThe serum concentration of Isoniazid can be decreased when it is combined with Dexamethasone.
DisulfiramThe risk or severity of adverse effects can be increased when Disulfiram is combined with Isoniazid.
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Isoniazid.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Isoniazid.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Isoniazid.
EthionamideThe serum concentration of Isoniazid can be increased when it is combined with Ethionamide.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Isoniazid.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Isoniazid.
FludrocortisoneThe serum concentration of Isoniazid can be decreased when it is combined with Fludrocortisone.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Isoniazid.
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Isoniazid.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Isoniazid.
HydrocortisoneThe serum concentration of Isoniazid can be decreased when it is combined with Hydrocortisone.
IsofluraneThe metabolism of Isoflurane can be decreased when combined with Isoniazid.
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Isoniazid.
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Isoniazid.
LevodopaThe therapeutic efficacy of Levodopa can be decreased when used in combination with Isoniazid.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Isoniazid.
Magnesium hydroxideMagnesium hydroxide can cause a decrease in the absorption of Isoniazid resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Isoniazid resulting in a reduced serum concentration and potentially a decrease in efficacy.
MethylprednisoloneThe serum concentration of Isoniazid can be decreased when it is combined with Methylprednisolone.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Isoniazid.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Isoniazid.
NicotineThe metabolism of Nicotine can be decreased when combined with Isoniazid.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Isoniazid.
PantoprazoleThe metabolism of Pantoprazole can be decreased when combined with Isoniazid.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Isoniazid.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Isoniazid.
PrednisoloneThe serum concentration of Isoniazid can be decreased when it is combined with Prednisolone.
PrednisoneThe serum concentration of Isoniazid can be decreased when it is combined with Prednisone.
PropacetamolIsoniazid may increase the hepatotoxic activities of Propacetamol.
PropafenoneThe serum concentration of Isoniazid can be increased when it is combined with Propafenone.
Repository corticotropinThe serum concentration of Isoniazid can be decreased when it is combined with Repository corticotropin.
RifabutinRifabutin may increase the hepatotoxic activities of Isoniazid.
RifampicinRifampicin may increase the hepatotoxic activities of Isoniazid.
RifapentineRifapentine may increase the hepatotoxic activities of Isoniazid.
SevofluraneThe metabolism of Sevoflurane can be decreased when combined with Isoniazid.
Sodium bicarbonateSodium bicarbonate can cause a decrease in the absorption of Isoniazid resulting in a reduced serum concentration and potentially a decrease in efficacy.
TamoxifenThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Isoniazid resulting in a loss in efficacy.
TegafurThe serum concentration of the active metabolites of Tegafur can be reduced when Tegafur is used in combination with Isoniazid resulting in a loss in efficacy.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Isoniazid.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Isoniazid.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Isoniazid.
TramadolThe therapeutic efficacy of Tramadol can be decreased when used in combination with Isoniazid.
TriamcinoloneThe serum concentration of Isoniazid can be decreased when it is combined with Triamcinolone.
Food Interactions
  • Avoid aged foods (cheese, red wine), pickled foods, cured foods (bacon/ham), chocolate, fava beans, beer, unless approved by your physician.
  • Avoid alcohol.
  • Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication.
  • Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
  • Take on empty stomach: 1 hour before or 2 hours after meals.
  • Take with a full glass of water.

Targets

1. Catalase-peroxidase

Kind: Protein

Organism: Mycobacterium tuberculosis

Pharmacological action: yes

Actions: other/unknown

Components

Name UniProt ID Details
Catalase-peroxidase Q08129 Details

References:

  1. Pym AS, Domenech P, Honore N, Song J, Deretic V, Cole ST: Regulation of catalase-peroxidase (KatG) expression, isoniazid sensitivity and virulence by furA of Mycobacterium tuberculosis. Mol Microbiol. 2001 May;40(4):879-89. Pubmed
  2. Heym B, Alzari PM, Honore N, Cole ST: Missense mutations in the catalase-peroxidase gene, katG, are associated with isoniazid resistance in Mycobacterium tuberculosis. Mol Microbiol. 1995 Jan;15(2):235-45. Pubmed
  3. Wilson TM, de Lisle GW, Collins DM: Effect of inhA and katG on isoniazid resistance and virulence of Mycobacterium bovis. Mol Microbiol. 1995 Mar;15(6):1009-15. Pubmed
  4. Vilcheze C, Jacobs WR Jr: The mechanism of isoniazid killing: clarity through the scope of genetics. Annu Rev Microbiol. 2007;61:35-50. Pubmed

2. Enoyl-[acyl-carrier-protein] reductase [NADH]

Kind: Protein

Organism: Mycobacterium tuberculosis

Pharmacological action: yes

Actions: adduct

Components

Name UniProt ID Details
Enoyl-[acyl-carrier-protein] reductase [NADH] P0A5Y6 Details

References:

  1. Schroeder EK, Basso LA, Santos DS, de Souza ON: Molecular dynamics simulation studies of the wild-type, I21V, and I16T mutants of isoniazid-resistant Mycobacterium tuberculosis enoyl reductase (InhA) in complex with NADH: toward the understanding of NADH-InhA different affinities. Biophys J. 2005 Aug;89(2):876-84. Epub 2005 May 20. Pubmed
  2. Wilson TM, de Lisle GW, Collins DM: Effect of inhA and katG on isoniazid resistance and virulence of Mycobacterium bovis. Mol Microbiol. 1995 Mar;15(6):1009-15. Pubmed
  3. Broussy S, Coppel Y, Nguyen M, Bernadou J, Meunier B: 1H and 13C NMR characterization of hemiamidal isoniazid-NAD adducts as possible inhibitors of InhA reductase of Mycobacterium tuberculosis. Chemistry. 2003 May 9;9(9):2034-8. Pubmed
  4. Vilcheze C, Jacobs WR Jr: The mechanism of isoniazid killing: clarity through the scope of genetics. Annu Rev Microbiol. 2007;61:35-50. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Cytochrome P450 2C8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Fontana E, Dansette PM, Poli SM: Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab. 2005 Oct;6(5):413-54. Pubmed

4. Cytochrome P450 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Fontana E, Dansette PM, Poli SM: Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab. 2005 Oct;6(5):413-54. Pubmed

5. Cytochrome P450 3A4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Fontana E, Dansette PM, Poli SM: Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab. 2005 Oct;6(5):413-54. Pubmed

6. Cytochrome P450 2C19

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Fontana E, Dansette PM, Poli SM: Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab. 2005 Oct;6(5):413-54. Pubmed

7. Dihydrofolate reductase

Kind: Protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Components

Name UniProt ID Details
Dihydrofolate reductase P0A546 Details

References:

  1. Wang F, Jain P, Gulten G, Liu Z, Feng Y, Ganesula K, Motiwala AS, Ioerger TR, Alland D, Vilcheze C, Jacobs WR Jr, Sacchettini JC: Mycobacterium tuberculosis dihydrofolate reductase is not a target relevant to the antitubercular activity of isoniazid. Antimicrob Agents Chemother. 2010 Sep;54(9):3776-82. doi: 10.1128/AAC.00453-10. Epub 2010 Jun 21. Pubmed

Enzymes

1. Cytochrome P450 2E1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

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

2. Cytochrome P450 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. Pubmed
  2. 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 2C9

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. 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

4. 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

5. Cytochrome P450 2C19

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 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

6. 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

7. Arylamine N-acetyltransferase 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Arylamine N-acetyltransferase 2 P11245 Details

References:

  1. Upton AM, Mushtaq A, Victor TC, Sampson SL, Sandy J, Smith DM, van Helden PV, Sim E: Arylamine N-acetyltransferase of Mycobacterium tuberculosis is a polymorphic enzyme and a site of isoniazid metabolism. Mol Microbiol. 2001 Oct;42(2):309-17. Pubmed

8. Arylamine N-acetyltransferase

Kind: Protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Arylamine N-acetyltransferase P0A5L8 Details

References:

  1. Upton AM, Mushtaq A, Victor TC, Sampson SL, Sandy J, Smith DM, van Helden PV, Sim E: Arylamine N-acetyltransferase of Mycobacterium tuberculosis is a polymorphic enzyme and a site of isoniazid metabolism. Mol Microbiol. 2001 Oct;42(2):309-17. Pubmed

9. Cytochrome P450 2A6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 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

10. Cytochrome P450 2C8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12