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.
OverviewAI-generated
Isoniazid is a chemical compound with the formula C₆H₇N₃O. Its IUPAC name is pyridine-4-carbohydrazide, and it has a canonical SMILES representation of C1=CN=CC=C1C(=O)NN. The substance has a mass of 137.059 and a melting point of 172. It is classified under the MCN code 2933.39.92.
Chemical properties include an xlogp of -0.7, a topological polar surface area of 68, and a charge of 0. The molecule contains two hydrogen bond donors and three hydrogen bond acceptors. PubChem lists its weight as 137.14.
Isoniazid is referenced by 1,224 other encyclopedia articles. A PubMed query for the term yields a count of 28,800 entries.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
- Has part
- carbon
- Mass
- 137.059
- Has use
- medication
Show 9 more facts
- medical condition treated
- tuberculosis
- chemical formula
- C₆H₇N₃O
- canonical SMILES
- C1=CN=CC=C1C(=O)NN
- subject has role
- bactericide
- melting point
- 172
- Commons category
- Isoniazid
- MCN code
- 2933.39.92
- legal status (medicine)
- boxed warning
- significant drug interaction
- disulfiram
Sources (7)
via Wikidata · CC0
~14 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “isoniazid” article, available under the CC BY-SA 4.0 licence.