Structure via PubChem · Public domain (PubChem)
metisazone
Sign in to saveAlso known as methisazone
Methisazone (USAN) or metisazone (INN) is an antiviral drug that works by inhibiting mRNA and protein synthesis, especially in pox viruses. During trials in the 1960s it showed promising results against smallpox infection, but widespread use was considered logistically impractical in the developing countries facing smallpox cases, and it saw only limited use. In developed countries able to cope with the logistic challenge, treatment of smallpox could be achieved just as effectively with immunoglobulin therapy, without the severe nausea associated with metisazone.
Chemical data
- Formula
- C10H10N4OS
- Molecular weight
- 234.28 g/mol
- IUPAC name
- (2-hydroxy-1-methylindol-3-yl)iminothiourea
- SMILES
- CN1C2=CC=CC=C2C(=C1O)N=NC(=S)N
- InChIKey
- TTZUCVNWOZLIGL-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 108 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- viral disease
via ChEMBL · EBI
Research
132 papers- Progressive vaccinia.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2003
- Rethinking smallpox.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2004
- Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives.Archiv der Pharmazie · 2019
- Ligand-Promoted Fluorinated Olefination of Isatins at the C5 Position via a Palladium Catalyst.Organic letters · 2022
- Arenavirus chemotherapy--retrospect and prospect.Bulletin of the World Health Organization · 1975
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 234.057532
Show 3 more facts
- canonical SMILES
- CN1C2=CC=CC=C2C(=NNC(=S)N)C1=O
- chemical formula
- C₁₀H₁₀N₄OS
- Commons category
- Methisazone
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Methisazone (USAN) or metisazone (INN) is an antiviral drug that works by inhibiting mRNA and protein synthesis, especially in pox viruses. During trials in the 1960s it showed promising results against smallpox infection, but widespread use was considered logistically impractical in the developing countries facing smallpox cases, and it saw only limited use. In developed countries able to cope with the logistic challenge, treatment of smallpox could be achieved just as effectively with immunoglobulin therapy, without the severe nausea associated with metisazone.
Methisazone has been described as being used in prophylaxis since at least 1965.
Excerpted from Wikipedia’s “metisazone” article, available under the CC BY-SA 4.0 licence.