Identification

Name
Isoniazid
Accession Number
DB00951  (APRD01055, EXPT01940)
Type
Small Molecule
Groups
Approved, Investigational
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 IDs
NSC-9659
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IsoniazidTablet100 mg/1OralPd Rx Pharmaceuticals, Inc.1978-12-11Not applicableUs
IsoniazidTablet300 mg/1OralEon Labs, Inc.1978-12-11Not applicableUs0185 435020180907 15195 1gwklmc
IsoniazidTablet100 mg/1OralRemedy Repack2016-09-012016-09-01Us
IsoniazidTablet300 mg/1OralPreferreed Pharmaceuticals Inc.2015-10-07Not applicableUs00185 4350 01 nlmimage10 6b083581
IsoniazidTablet300 mg/1OralPd Rx Pharmaceuticals, Inc.1978-12-11Not applicableUs
IsoniazidTablet300 mg/1OralRemedy Repack2011-12-072012-12-07Us
IsoniazidTablet300 mg/1OralRemedy Repack2013-03-202014-05-01Us
IsoniazidTablet100 mg/1OralRemedy Repack2016-05-04Not applicableUs
IsoniazidTablet100 mg/1OralEon Labs, Inc.1978-12-11Not applicableUs
IsoniazidTablet100 mg/1OralRemedy Repack2016-09-012016-09-01Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-isoniazid 300mg TabletsTablet300 mgOralDominion Pharmacal1995-12-31Not applicableCanada
IsoniazidTablet300 mg/1OralMikart, Inc.1997-06-26Not applicableUs
IsoniazidTablet100 mg/1OralREMEDYREPACK INC.2013-09-252017-06-09Us
IsoniazidTablet300 mg/1OralAmerincan Health Packaging2016-02-23Not applicableUs
IsoniazidTablet100 mg/1Oralbryant ranch prepack1972-09-01Not applicableUs63629 370720180907 15195 1n1iu15
IsoniazidTablet300 mg/1OralProficient Rx LP1972-09-01Not applicableUs
IsoniazidTablet100 mg/1OralDepartment Of State Health Services, Pharmacy Branch1972-09-01Not applicableUs
IsoniazidTablet300 mg/1OralA S Medication Solutions1972-09-01Not applicableUs00555 0071 01 nlmimage10 bf2b5faa
IsoniazidTablet100 mg/1OralRemedy Repack2013-02-012014-09-12Us
IsoniazidTablet300 mg/1Oralbryant ranch prepack1981-07-14Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
IsonaRifIsoniazid (150 mg/1) + Rifampicin (300 mg/1)CapsuleOralVersaPharm Incorporated1997-07-21Not applicableUs
Isotamine B 300Isoniazid (300 mg) + Pyridoxine hydrochloride (15 mg)TabletOralValeant Canada Lp Valeant Canada S.E.C.1967-12-31Not applicableCanada
RifamateIsoniazid (150 mg/1) + Rifampicin (300 mg/1)CapsuleOralsanofi-aventis U.S. LLC1975-07-11Not applicableUs
RifaterIsoniazid (50 mg) + Pyrazinamide (300 mg) + Rifampicin (120 mg)TabletOralSanofi Aventis1995-12-312017-03-29Canada
RifaterIsoniazid (50 mg/1) + Pyrazinamide (300 mg/1) + Rifampicin (120 mg/1)Tablet, sugar coatedOralsanofi-aventis U.S. LLC1994-05-31Not applicableUs
RifaterIsoniazid (50 mg/1) + Pyrazinamide (300 mg/1) + Rifampicin (120 mg/1)Tablet, sugar coatedOralRemedy Repack2010-09-152010-09-16Us
International/Other Brands
Nicozid (Piam) / Nidrazid (Zentiva) / Nydrazid (Sandoz) / Rimicid (Sopharma) / Rimifon (Roche) / Servizid (Novartis) / Tibinide (Meda)
Categories
UNII
V83O1VOZ8L
CAS number
54-85-3
Weight
Average: 137.1393
Monoisotopic: 137.058911861
Chemical Formula
C6H7N3O
InChI Key
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

Pharmacology

Indication

For the treatment of all forms of tuberculosis in which organisms are susceptible.

Associated Conditions
Pharmacodynamics

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.

Mechanism of action

Isoniazid 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.

TargetActionsOrganism
ACatalase-peroxidase
other/unknown
Mycobacterium tuberculosis
AEnoyl-[acyl-carrier-protein] reductase [NADH]
adduct
Mycobacterium tuberculosis
UCytochrome P450 2C8Not AvailableHuman
UCytochrome P450 1A2Not AvailableHuman
UCytochrome P450 3A4Not AvailableHuman
UCytochrome P450 2C19Not AvailableHuman
UDihydrofolate reductaseNot AvailableMycobacterium tuberculosis
Absorption

Readily absorbed following oral administration; however, may undergo significant first pass metabolism. Absorption and bioavailability are reduced when isoniazid is administered with food.

Volume of distribution
Not Available
Protein binding

Very 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 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.

Clearance
Not Available
Toxicity

LD50 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2E1CYP2E1*4(A;A)---ADR Directly StudiedThe presence of this genotype in CYP2E1 may be associated with an increased risk of drug-induced hepatotoxicity from isoniazid treatment.Details
Arylamine N-acetyltransferase 1NAT1*14ANot AvailableG > A | T > A | C > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 1NAT1*14BNot AvailableG > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 1NAT1*15Not AvailableC > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 1NAT1*17Not AvailableC > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 1NAT1*19ANot AvailableC > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 1NAT1*19BNot AvailableC > T | C > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 1NAT1*22Not AvailableA > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5ANot AvailableT > C | C > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5BNot AvailableT > C | C > T | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5CNot AvailableT > C | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5DNot AvailableT > CADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5ENot AvailableT > C | G > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5FNot AvailableT > C | C > T | C > T | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5GNot AvailableT > C | C > T | C > T | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5HNot AvailableT > C | C > T | A > G | S287 FrameshiftADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5INot AvailableT > C | C > T | A > T | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*5JNot AvailableT > C | C > T | G > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*6ANot AvailableG > A | C > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*6BNot AvailableG > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*6CNot AvailableG > A | C > T | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*6DNot AvailableG > A | C > T | T > CADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*6ENot AvailableG > A | C > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*7ANot AvailableG > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*7BNot AvailableG > A | C > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*10Not AvailableG > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*12DNot AvailableG > A | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*14ANot AvailableG > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*14BNot AvailableG > A | C > TADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*14CNot AvailableG > A | T > C | C > T | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*14DNot AvailableG > A | C > T | G > AADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*14ENot AvailableG > A | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*14FNot AvailableG > A | T > C | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*14GNot AvailableG > A | C > T | A > GADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*17Not AvailableA > CADR InferredIncreased risk of toxic reactions.Details
Arylamine N-acetyltransferase 2NAT2*19Not AvailableC > TADR InferredIncreased risk of toxic reactions.Details

Interactions

Drug Interactions
DrugInteraction
16-BromoepiandrosteroneThe serum concentration of Isoniazid can be decreased when it is combined with 16-Bromoepiandrosterone.
19-norandrostenedioneThe serum concentration of Isoniazid can be decreased when it is combined with 19-norandrostenedione.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Isoniazid.
5-androstenedioneThe serum concentration of Isoniazid can be decreased when it is combined with 5-androstenedione.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Isoniazid.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Isoniazid.
AcetaminophenThe risk or severity of adverse effects can be increased when Isoniazid is combined with Acetaminophen.
AcetylcholineThe metabolism of Acetylcholine can be decreased when combined with Isoniazid.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Isoniazid which could result in a higher serum level.
Adefovir DipivoxilAdefovir Dipivoxil may decrease the excretion rate of Isoniazid which could result in a higher serum level.
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.

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 References
Not Available
External Links
Human Metabolome Database
HMDB0015086
KEGG Drug
D00346
KEGG Compound
C07054
PubChem Compound
3767
PubChem Substance
46506039
ChemSpider
3635
BindingDB
50336507
ChEBI
6030
ChEMBL
CHEMBL64
Therapeutic Targets Database
DAP000011
PharmGKB
PA450112
HET
NIZ
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Isoniazid
ATC Codes
J04AM04 — Thioacetazone and isoniazidJ04AM06 — Rifampicin, pyrazinamide, ethambutol and isoniazidJ04AM02 — Rifampicin and isoniazidJ04AM01 — Streptomycin and isoniazidJ04AM05 — Rifampicin, pyrazinamide and isoniazidJ04AM03 — Ethambutol and isoniazidJ04AC01 — IsoniazidJ04AC51 — Isoniazid, combinations
AHFS Codes
  • 08:16.04 — Antituberculosis Agents
PDB Entries
3wxo / 4pae / 5ksg / 5ksn / 5kt8 / 5sxq / 5sxs / 5sxt / 5syi / 5syj
show 2 more
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
0RecruitingTreatmentTuberculosis1
1CompletedOtherTuberculosis2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis2
1CompletedTreatmentTuberculosis2
1RecruitingOtherHealthy Volunteers2
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
1RecruitingTreatmentTuberculosis1
1, 2Active Not RecruitingTreatmentTuberculosis1
1, 2CompletedNot AvailableDiabetes, Diabetes Mellitus Type 11
1, 2CompletedTreatmentTB Multi-drug Resistant1
1, 2RecruitingTreatmentTuberculous Meningitis1
2Active Not RecruitingPreventionTuberculosis1
2CompletedTreatmentTuberculosis4
2CompletedTreatmentTuberculosis, Pulmonary1
2RecruitingTreatmentDrug-resistant Tuberculosis / Drug-Resistant Tuberculosis, Extremely / Tuberculosis / Tuberculosis, MDR / Tuberculosis, Multidrug Resistant / Tuberculosis, Pulmonary1
2RecruitingTreatmentTuberculosis1
2SuspendedTreatmentTuberculosis, Pulmonary1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
2TerminatedTreatmentTuberculosis1
2Unknown StatusTreatmentTuberculosis1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
2, 3CompletedTreatmentTuberculosis, Multidrug Resistant1
2, 3Enrolling by InvitationPreventionTuberculosis1
2, 3Not Yet RecruitingTreatmentTuberculosis, Pulmonary1
2, 3RecruitingTreatmentExtensively-drug Resistant Tuberculosis / Tuberculosis / Tuberculosis, Multidrug Resistant1
2, 3RecruitingTreatmentTuberculosis, Pulmonary1
2, 3TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Interstitial Plasma Cell / Tuberculosis1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) / Tuberculosis1
3Active Not RecruitingPreventionLatent Tuberculosis Infection (LTI)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis, Pulmonary1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis2
3CompletedPreventionHuman Immunodeficiency Virus (HIV) / Tuberculosis1
3CompletedPreventionLatent Tuberculosis Infection (LTI)1
3CompletedPreventionTuberculosis1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Tuberculosis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
3CompletedTreatmentLatent Tuberculosis Infection (LTI)2
3CompletedTreatmentTuberculosis3
3CompletedTreatmentTuberculosis, Pulmonary2
3CompletedTreatmentTuberculosis, Pulmonary, Drug Sensitive / Tuberculosis, Pulmonary, Multi Drug-resistant1
3Not Yet RecruitingPreventionTuberculosis, MDR1
3RecruitingPreventionSilicosis / Tuberculosis1
3RecruitingTreatmentMDR-TB1
3RecruitingTreatmentTuberculosis1
3TerminatedTreatmentInfection in Solid Organ Transplant Recipients / Latent Tuberculosis Infection (LTI)1
3TerminatedTreatmentMultiple System Atrophy (MSA)1
3TerminatedTreatmentTuberculosis, Pulmonary1
3Unknown StatusPreventionTuberculosis1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4Active Not RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4Active Not RecruitingTreatmentDiabetes Mellitus (DM) / Tuberculin (Skin Test) Positive1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedDiagnosticTuberculosis1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4CompletedTreatmentTuberculosis, Pulmonary1
4RecruitingHealth Services ResearchAddictions / Hepatitis / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Opioid Dependence / Tuberculosis1
4RecruitingOtherAlcohol Abuse / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Tuberculosis1
4RecruitingTreatmentAIDS With Tuberculosis1
4RecruitingTreatmentCompliance, Patient1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingTreatmentTuberculosis, Pulmonary1
4RecruitingTreatmentTuberculosis, Spinal1
4Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Latent Tuberculosis Infection (LTI) / Tuberculosis (TB)1
4Unknown StatusTreatmentHepatitis / Tuberculosis, Pulmonary1
4Unknown StatusTreatmentHepatotoxicity / Tuberculosis1
4Unknown StatusTreatmentReinfection Pulmonary Tuberculosis1
4WithdrawnPreventionDiabetes Mellitus (DM) / Late phase Tuberculosis1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Latent Tuberculosis Infection (LTI) / Tuberculosis1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
Not AvailableCompletedSupportive CareBody Weight Changes / Motor Activities / Tuberculosis, Pulmonary1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis4
Not AvailableCompletedTreatmentKidney Transplant Recipients1
Not AvailableCompletedTreatmentTuberculosis2
Not AvailableRecruitingNot AvailableTuberculosis1
Not AvailableRecruitingPreventionAdverse Drug Events / Drug-Induced Liver Injury / Tuberculosis1
Not AvailableRecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Tuberculosis, Pulmonary1
Not AvailableRecruitingTreatmentDrug-resistant Tuberculosis / Tuberculosis / Tuberculosis, Multidrug Resistant1
Not AvailableTerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Tuberculosis1
Not AvailableTerminatedTreatmentErythropoietic Protoporphyria (EPP) / X Linked Erythropoietic Protoporphyria1
Not AvailableUnknown StatusNot AvailableTuberculosis, Pulmonary1
Not AvailableUnknown StatusPreventionTuberculosis1
Not AvailableUnknown StatusSupportive CareHepatotoxicity1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1

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
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Amend
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Blenheim Pharmacal
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Carolina Medical Products Co.
  • Consolidated Midland Corp.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • E.R. Squibb and Sons LLC
  • Eon Labs
  • Golden State Medical Supply Inc.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Huffman Laboratories
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nexgen Pharma Inc.
  • Nucare Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Sandoz
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • UDL Laboratories
  • Versapharm Inc.
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
CapsuleOral50 mg/5mL
Injection, solutionIntramuscular100 mg/1mL
SolutionOral50 mg/5mL
SyrupOral50 mg/5mL
TabletOral100 mg/1
TabletOral300 mg/1
SyrupOral50 mg
TabletOral50 mg
PowderOral500 g
SyrupOral10 mg
SolutionOral50 mg
TabletOral100 mg
TabletOral300 mg
CapsuleOral
TabletOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)171.4 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0kdr-9600000000-f04526999a9b68d31861
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0900000000-3cf8f43d0df46334dcd9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-052r-7900000000-3d43394feacded48669d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-263a0bcadf2e21536983
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-002f-9000000000-17100430370d37f834ce
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-9466b9291244c1a61f01
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0900000000-afcf227eec118bec08a4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-1900000000-d63af1f463124dbf7b65
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00fr-9600000000-1d50dedb0eea7ff8dccb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9100000000-371fd6d67c48f373e2e5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9000000000-dee0012ebd004444b3d8
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridinecarboxylic acids and derivatives
Direct Parent
Pyridinecarboxylic acids and derivatives
Alternative Parents
Heteroaromatic compounds / Carboxylic acid hydrazides / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
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
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
carbohydrazide (CHEBI:6030) / a small molecule (ISONIAZIDE)

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Yes
Actions
Other/unknown
General Function
Bifunctional enzyme with both catalase and broad-spectrum peroxidase activity, oxidizing various electron donors including NADP(H) (PubMed:9006925, PubMed:18178143). Protects M.tuberculosis against toxic reactive oxygen species (ROS) including hydrogen peroxide as well as organic peroxides and thus contributes to its survival within host macrophages by countering the phagocyte oxidative burst (PubMed:8658136, PubMed:15165233). Also displays efficient peroxynitritase activity, which may help the bacterium to persist in macrophages (PubMed:10080924).
Specific Function
Catalase activity
Gene Name
katG
Uniprot ID
P9WIE5
Uniprot Name
Catalase-peroxidase
Molecular Weight
80604.275 Da
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:11401695]
  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:7746145]
  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:7623658]
  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:18035606]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Yes
Actions
Adduct
General Function
Enoyl-ACP reductase of the type II fatty acid syntase (FAS-II) system, which is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls (PubMed:25227413). Catalyzes the NADH-dependent reduction of the double bond of 2-trans-enoyl-[acyl-carrier protein], an essential step in the fatty acid elongation cycle of the FAS-II pathway (PubMed:7599116). Shows preference for long-chain fatty acyl thioester substrates (>C16), and can also use 2-trans-enoyl-CoAs as alternative substrates (PubMed:7599116). The mycobacterial FAS-II system utilizes the products of the FAS-I system as primers to extend fatty acyl chain lengths up to C56, forming the meromycolate chain that serves as the precursor for final mycolic acids (PubMed:25227413).
Specific Function
Enoyl-[acyl-carrier-protein] reductase (nadh) activity
Gene Name
inhA
Uniprot ID
P9WGR1
Uniprot Name
Enoyl-[acyl-carrier-protein] reductase [NADH]
Molecular Weight
28527.55 Da
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:15908576]
  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:7623658]
  3. Broussy S, Coppel Y, Nguyen M, Bernadou J, Meunier B: 1H and 13C NMR characterization of hemiamidal isoniazid-NAD(H) adducts as possible inhibitors of InhA reductase of Mycobacterium tuberculosis. Chemistry. 2003 May 9;9(9):2034-8. [PubMed:12740851]
  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:18035606]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
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:16248836]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
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:16248836]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
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:16248836]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
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:16248836]
Details
7. Dihydrofolate reductase
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Specific Function
Dihydrofolate reductase activity
Gene Name
folA
Uniprot ID
P9WNX1
Uniprot Name
Dihydrofolate reductase
Molecular Weight
17872.18 Da
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:20566771]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Polasek TM, Elliot DJ, Lewis BC, Miners JO: Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. J Pharmacol Exp Ther. 2004 Dec;311(3):996-1007. doi: 10.1124/jpet.104.071803. Epub 2004 Aug 10. [PubMed:15304522]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
Curator comments
Isoniazid tends to inhibit 2E1 while it is in the body, followed by induction once it is stopped and its plasma concentration becomes undetectable - CPS Compendium of Pharmaceuticals and Specialties.
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Madan A, Graham RA, Carroll KM, Mudra DR, Burton LA, Krueger LA, Downey AD, Czerwinski M, Forster J, Ribadeneira MD, Gan LS, LeCluyse EL, Zech K, Robertson P Jr, Koch P, Antonian L, Wagner G, Yu L, Parkinson A: Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos. 2003 Apr;31(4):421-31. [PubMed:12642468]
  2. Zand R, Nelson SD, Slattery JT, Thummel KE, Kalhorn TF, Adams SP, Wright JM: Inhibition and induction of cytochrome P4502E1-catalyzed oxidation by isoniazid in humans. Clin Pharmacol Ther. 1993 Aug;54(2):142-9. [PubMed:8354023]
  3. Caro AA, Cederbaum AI: Inhibition of CYP2E1 catalytic activity in vitro by S-adenosyl-L-methionine. Biochem Pharmacol. 2005 Apr 1;69(7):1081-93. [PubMed:15763544]
  4. Spracklin DK, Emery ME, Thummel KE, Kharasch ED: Concordance between trifluoroacetic acid and hepatic protein trifluoroacetylation after disulfiram inhibition of halothane metabolism in rats. Acta Anaesthesiol Scand. 2003 Jul;47(6):765-70. [PubMed:12803597]
  5. Leclercq I, Desager JP, Horsmans Y: Inhibition of chlorzoxazone metabolism, a clinical probe for CYP2E1, by a single ingestion of watercress. Clin Pharmacol Ther. 1998 Aug;64(2):144-9. doi: 10.1016/S0009-9236(98)90147-3. [PubMed:9728894]
  6. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L57). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Clin-info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L56). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Details
4. Cytochrome P450 1A2
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
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:19754423]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L56). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Details
6. Cytochrome P450 2C19
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Nishimura Y, Kurata N, Sakurai E, Yasuhara H: Inhibitory effect of antituberculosis drugs on human cytochrome P450-mediated activities. J Pharmacol Sci. 2004 Nov;96(3):293-300. Epub 2004 Nov 5. [PubMed:15528841]
  3. Desta Z, Soukhova NV, Flockhart DA: Inhibition of cytochrome P450 (CYP450) isoforms by isoniazid: potent inhibition of CYP2C19 and CYP3A. Antimicrob Agents Chemother. 2001 Feb;45(2):382-92. doi: 10.1128/AAC.45.2.382-392.2001. [PubMed:11158730]
  4. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L56). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Arylamine n-acetyltransferase activity
Specific Function
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name
NAT2
Uniprot ID
P11245
Uniprot Name
Arylamine N-acetyltransferase 2
Molecular Weight
33542.235 Da
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:11703656]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Catalyzes the transfer of the acetyl group from acetyl coenzyme A to the free amino group of arylamines and hydrazines (PubMed:18795795). Is able to utilize not only acetyl-CoA, but also n-propionyl-CoA and acetoacetyl-CoA as acyl donors, although at a lower rate (PubMed:19014350). As acetyl-CoA and propionyl-CoA are products of cholesterol catabolism and the nat gene is likely present in the same operon than genes involved in cholesterol degradation, this enzyme could have a role in the utilization and regulation of these CoA species (PubMed:19014350).
Specific Function
Arylamine n-acetyltransferase activity
Gene Name
nat
Uniprot ID
P9WJI5
Uniprot Name
Arylamine N-acetyltransferase
Molecular Weight
31028.88 Da
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:11703656]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L56). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Meng X, Maggs JL, Usui T, Whitaker P, French NS, Naisbitt DJ, Park BK: Auto-oxidation of Isoniazid Leads to Isonicotinic-Lysine Adducts on Human Serum Albumin. Chem Res Toxicol. 2015 Jan 20;28(1):51-8. doi: 10.1021/tx500285k. Epub 2014 Dec 9. [PubMed:25489718]

Drug created on June 13, 2005 07:24 / Updated on September 25, 2018 17:45