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
1910-68-5 YesY
ATC code J05AA01
ChEMBL ChEMBL1512080 N
ChemSpider 5259074
EC number 217-616-2
Jmol-3D images Image
KEGG D02496
MeSH D008720
PubChem 6861563
UNII K3QML4J07E N
Properties
C10H10N4OS
Molar mass 234.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

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]

Synthesis[edit]

Methisazone synthesis: Bauer, Sadler, Br. J. Pharmacol. 15, 101 (1960); GB 975357  (1964 to Wellcome Foundation).

When isatin is treated with NaH and MeI, the acidic hydrogen is alkylated to product 2. Then, reaction of the ketone carbonyl with thiosemicarbazine (3) leads to methisazone (4).

References[edit]

  1. ^ Methisazone, 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. 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.