Metisazone

Metisazone

Names
IUPAC name [(1-Methyl-2-oxoindol-3-ylidene)amino]thiourea
Other names Metisazone
Identifiers
CAS Number	1910-68-5
ChEMBL	ChEMBL1512080
ChemSpider	5259074
EC Number	217-616-2
Jmol interactive 3D	Image
KEGG	D02496
MeSH	D008720
PubChem	6861563
UNII	K3QML4J07E
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 CN1C2=CC=CC=C2C(=NNC(=S)N)C1=O
Properties
Chemical formula	C10H10N4OS
Molar mass	234.28 g/mol
Pharmacology
ATC code	J05AA01
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) 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

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

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. 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.