Metisazone

Metisazone
Names
	IUPAC name [(1-Methyl-2-oxoindol-3-ylidene)amino]thiourea
	Other names Metisazone
Identifiers
CAS Number	1910-68-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1512080 ;
ChemSpider	5259074;
ECHA InfoCard	100.016.016
EC Number	217-616-2;
KEGG	D02496;
MeSH	D008720
PubChem CID	6861563;
UNII	K3QML4J07E ;
CompTox Dashboard (EPA)	DTXSID7046413 ;
	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
ATC code	J05AA01 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

References

^ 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
^ Fenner, Frank; Henderson, Donald A; Arita, Isa; Jezek, Zdenek; Ladnyi, Ivan Danilovich (1988). Smallpox and its eradication. Geneva: World Health Organization. p. 67. ISBN 9241561106.
^ 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.
^ 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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[Potopalsky-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. ISBN 9241561106.

[pmid4159212-3] 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.

[pmid15578369-4] 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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