Metisazone

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

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
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
  • CN1C(=O)C(=NNC(N)=S)c2ccccc21
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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Infobox references

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. Fenner, Frank; Henderson, Donald A; Arita, Isa; Jezek, Zdenek; Ladnyi, Ivan Danilovich (1988). Smallpox and its eradication. Geneva: World Health Organization. p. 67. hdl:10665/39485. ISBN 9241561106.
  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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