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
  • 1910-68-5 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1512080 ☒N
ChemSpider
  • 5259074
ECHA InfoCard 100.016.016 Edit this at Wikidata
EC Number
  • 217-616-2
KEGG
  • D02496
MeSH D008720
PubChem CID
  • 6861563
UNII
  • K3QML4J07E ☒N
CompTox Dashboard (EPA)
  • DTXSID7046413 Edit this at Wikidata
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
  • 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
Chemical compound

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]

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.[citation needed]

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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DNA virus antivirals (primarily J05, also S01AD and D06BB)
Baltimore I
Herpesvirus
DNA-synthesis
inhibitor
TK activated
Purine analogue
Pyrimidine analogue
Not TK activated
Other
HPV/MC
Vaccinia
Poxviridae
Hepatitis B (VII)Multiple/general
Nucleic acid inhibitors
Interferon
Multiple/unknown
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