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 CN1C2=CC=CC=C2C(=NNC(=S)N)C1=O;
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) 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

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

^ Methisazone, Merriam-Webster's Medical Dictionary
^ 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. PMID 15578369.

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[1] Methisazone, Merriam-Webster's Medical Dictionary

[pmid4159212-2] 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.

[pmid15578369-3] 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.

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