File:Isoniazid_skeletal.svg · Wikimedia Commons · See Wikimedia Commons
isoniazid
Sign in to saveAlso known as Rimifon, Stanozide, Laniazid, Pyridine-4-carboxylic acid hydrazide, Isonicotinsaeurehydrazid, Isonicotinohydrazide, 4-pyridinecarbohydrazide, INH
Isoniazid, also known as isonicotinic acid hydrazide (INH), is an antibiotic used for the treatment of tuberculosis. For active tuberculosis, it is often used together with rifampicin, pyrazinamide, and either streptomycin or ethambutol. It may also be used for atypical types of mycobacteria, such as M. avium, M. kansasii, and M. xenopi. It is usually taken by mouth, but may be used by injection into muscle.
Chemical data
- Formula
- C6H7N3O
- Molecular weight
- 137.14 g/mol
- IUPAC name
- pyridine-4-carbohydrazide
- SMILES
- C1=CN=CC=C1C(=O)NN
- InChIKey
- QRXWMOHMRWLFEY-UHFFFAOYSA-N
- XLogP
- -0.7
- Polar surface area
- 68 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
28,800 papers- [ISONIAZID AND VITAMIN B6].Le Poumon et le coeur · 1964
- [Primary isoniazid preventive therapy : A strategy still relevant in the era of test and treat ; literature review].Revue d'epidemiologie et de sante publique · 2022
- [Isoniazid].Revue de la tuberculose · 1953
- [Isoniazid].Concours medical · 1953
- Theophylline-isoniazid interaction.DICP : the annals of pharmacotherapy · 1989
via PubMed
Wikidata facts
- Mass
- 137.059
Show 5 more facts
- chemical formula
- C₆H₇N₃O
- canonical SMILES
- C1=CN=CC=C1C(=O)NN
- melting point
- 172
- Commons category
- Isoniazid
- MCN code
- 2933.39.92
Sources (7)
via Wikidata · CC0
~14 min read
Article
20 sectionsContents
- Medical uses
- Tuberculosis
- Non-tuberculous mycobacteria
- Special populations
- History
- Synthesis
- Discovery of anti-TB activity
- Elucidation of mechanism of action
- Modern usage
- Adverse effects
- Side effects
- Drug interactions
- Mechanism of action
- Metabolism
- Overdose
- Preparation
- Brand names
- Other uses
- Chromatography
- References
Isoniazid, also known as isonicotinic acid hydrazide (INH), is an antibiotic used for the treatment of tuberculosis. For active tuberculosis, it is often used together with rifampicin, pyrazinamide, and either streptomycin or ethambutol. It may also be used for atypical types of mycobacteria, such as M. avium, M. kansasii, and M. xenopi. It is usually taken by mouth, but may be used by injection into muscle.
Isoniazid is a prodrug that, when activated by catalase-peroxidase KatG, generates adducts and radicals that inhibits the formation of the mycobacterial cell wall. Side effects in those treated with isoniazid include vitamin B6 deficiency, liver toxicity, peripheral neuropathy, and a reduction in blood cell production. Mutations in the ahpC, inhA, kasA, katG, genes of M. tuberculosis may result in isoniazid resistance.