Structure via PubChem · Public domain (PubChem)
thioacetazone
Sign in to saveAlso known as Amithiozone
Thioacetazone (INN, BAN), also known as amithiozone (USAN), is an oral antibiotic which is used in the treatment of tuberculosis. It has fallen into almost complete disuse due to toxicity and the introduction of improved anti-tuberculosis drugs like isoniazid. The drug has only weak activity against Mycobacterium tuberculosis and is only useful in preventing resistance to more powerful drugs such as isoniazid and rifampicin. It is never used on its own to treat tuberculosis; it is used in a similar way to ethambutol.
Chemical data
- Formula
- C10H12N4OS
- Molecular weight
- 236.3 g/mol
- IUPAC name
- N-[4-[(E)-(carbamothioylhydrazinylidene)methyl]phenyl]acetamide
- SMILES
- CC(=O)NC1=CC=C(C=C1)/C=N/NC(=S)N
- InChIKey
- SRVJKTDHMYAMHA-WUXMJOGZSA-N
- XLogP
- 1
- Polar surface area
- 112 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- Mycobacterium avium complex disease, tuberculosis
via ChEMBL · EBI
Research
709 papers- Fluorescently labelled thioacetazone for detecting the interaction with Mycobacterium dehydratases HadAB and HadBC.Organic & biomolecular chemistry · 2022
- Tuberculosis.British medical journal · 1973
- Thioacetazone--a review.The Indian journal of chest diseases & allied sciences · 1982
- Tuberculosis--chemotherapy.British medical journal · 1972
- Further Insights into the Oxidative Pathway of Thiocarbonyl-Type Antitubercular Prodrugs: Ethionamide, Thioacetazone, and Isoxyl.Chemical research in toxicology · 2021
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 236.073
Show 5 more facts
- has characteristic
- bitterness
- chemical formula
- C₁₀H₁₂N₄OS
- Commons category
- Thioacetazone
- canonical SMILES
- CC(=O)NC1=CC=C(C=C1)C=NNC(=S)N
- isomeric SMILES
- CC(=O)NC1=CC=C(C=C1)/C=N/NC(=S)N
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Adverse effects
- See also
- References
- External links
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470606762 | IUPAC_name = N-{4-[(Ethanethioamidoimino)methyl]phenyl}acetamide | image = Thioacetazone.svg | image_class = skin-invert-image | alt = Structural formula of thioacetazone | width = 250 | image2 = Thioacetazone 3D spacefill.png | image_class2 = bg-transparent | alt2 = Space-filling model of thioacetazone | width2 = 225
| tradename = Conteben | Drugs.com = | routes_of_administration = Oral
Excerpted from Wikipedia’s “thioacetazone” article, available under the CC BY-SA 4.0 licence.