Metisazone

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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.016.016
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EC Number
  • 217-616-2
KEGG
MeSH D008720
PubChem CID
UNII
InChI
  • 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
SMILES
  • CN1C(=O)C(=NNC(N)=S)c2ccccc21
Properties
Chemical formula
 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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Infobox references

Methisazone (USAN) or metisazone (INN)[1] 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.[2]

Methisazone has been described as being used in prophylaxis since at least 1965.[3][4]

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

References

  1. ↑ Aromatic thiosemicarbazones, their antiviral action and interferon. 1. The decreasing of adenovirus type 1 resistance against interferon by methisazone in vitro, Yuriy V. Patskovsky*, Emma N. Negrebetskaya, Alexandra A. Chernomaz, Tamara P. Voloshchuk, Eugeniy L. Rubashevsky, Oleg E. Kitam, Mikhail I. Tereshchenko, Lidiya N. Nosach, Anatoliy I. Potopalsky
  2. ↑ Methisazone Archived 2012-07-10 at archive.today, Merriam-Webster's Medical Dictionary
  3. ↑ 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.
  4. ↑ Weiss MM, Weiss PD, Mathisen G, Guze P (December 2004). "Rethinking smallpox". Clin. Infect. Dis. 39 (11): 1668–73. doi:10.1086/425745. PMC 7107961. PMID 15578369.
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