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Metisazone

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Metisazone
Skeletal formula of methisazone
Space-filling model of the methisazone molecule
Names
IUPAC name
[(1-Methyl-2-oxoindol-3-ylidene)amino]thiourea
Other names
Metisazone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.016.016 Edit this at Wikidata
EC Number
  • 217-616-2
KEGG
MeSH D008720
UNII
  • InChI=1S/C10H10N4OS/c1-14-7-5-3-2-4-6(7)8(9(14)15)12-13-10(11)16/h2-5H,1H3,(H3,11,13,16)/b12-8-
    Key: DLGSOJOOYHWROO-WQLSENKSSA-N
  • InChI=1/C10H10N4OS/c1-14-7-5-3-2-4-6(7)8(9(14)15)12-13-10(11)16/h2-5H,1H3,(H3,11,13,16)/b12-8-
    Key: DLGSOJOOYHWROO-WQLSENKSBL
  • CN1C2=CC=CC=C2C(=NNC(=S)N)C1=O
Properties
C10H10N4OS
Molar mass 234.28 g/mol
Pharmacology
J05AA01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methisazone (USAN) or metisazone (INN) is an antiviral drug that works by inhibiting mRNA and protein synthesis, especially in pox viruses. It has been used in the past to treat smallpox.[1]

Methisazone has been described as being used in prophylaxis since at least 1965.[2][3]

The condensation of N-methylisatin with thiosemicarbazide leads to methisazone.

References

  1. ^ Methisazone Archived 2012-07-10 at archive.today, Merriam-Webster's Medical Dictionary
  2. ^ do Valle, LA; de Melo, PR; de Gomes, LF; Proença, LM (13 Nov 1965). "Methisazone in prevention of variola minor among contacts". Lancet. 2 (7420): 976–8. doi:10.1016/s0140-6736(65)92840-0. PMID 4159212.
  3. ^ Weiss MM, Weiss PD, Mathisen G, Guze P (December 2004). "Rethinking smallpox". Clin. Infect. Dis. 39 (11): 1668–73. doi:10.1086/425745. PMID 15578369.