Metisazone: Difference between revisions

| Verifiedfields = changed

| verifiedrevid = 384087307

| ImageFile = Methisazone.png

| ImageSize = 180

| ImageAlt = Skeletal formula of methisazone

| ImageFile1 = Methisazone-3D-spacefill.png

| ImageSize1 = 170

| ImageAlt1 = Space-filling model of the methisazone molecule

| IUPACName=[(1-Methyl-2-oxoindol-3-ylidene)amino]thiourea

| OtherNames=Metisazone

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=1910-68-5

| PubChem=6861563

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1512080

| EINECS = 217-616-2

| MeSHName = D008720

| ChEBI =

| KEGG = D02496

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = K3QML4J07E

| SMILES= CN1C(=O)C(=NNC(N)=S)c2ccccc21

| 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-

| InChIKey = DLGSOJOOYHWROO-WQLSENKSBL

| StdInChI = 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-

| StdInChIKey = DLGSOJOOYHWROO-WQLSENKSSA-N

| ChemSpiderID = 5259074

| Formula=C₁₀H₁₀N₄OS

| MolarMass=234.28 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

|Section6={{Chembox Pharmacology

| ATCCode_prefix = J05

| ATCCode_suffix = AA01

}}

|Section7={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

'''Methisazone''' ([[United States Adopted Name|USAN]]) or '''metisazone''' ([[International Nonproprietary Name|INN]])<ref name="Potopalsky">[http://www.biopolymers.org.ua/pdf/12/2/074/biopolym.cell-1996-12-2-074-en.pdf 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</ref> 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.<ref>{{cite book |last1=Fenner |first1=Frank |last2=Henderson |first2=Donald A |last3=Arita |first3=Isa |last4=Jezek |first4=Zdenek |last5=Ladnyi |first5=Ivan Danilovich |title=Smallpox and its eradication |date=1988 |publisher=World Health Organization |location=Geneva |isbn=9241561106 |page=67 |hdl=10665/39485 |url=https://apps.who.int/iris/handle/10665/39485}}</ref>

Methisazone has been described as being used in prophylaxis since at least 1965.<ref name="pmid4159212 ">{{Cite journal|pmid=4159212|journal=Lancet|date=13 Nov 1965|volume=2|issue=7420|pages=976–8|title=Methisazone in prevention of variola minor among contacts|last1=do Valle|first1=LA|last2=de Melo|first2=PR|last3=de Gomes|first3=LF|last4=Proença|first4=LM|doi=10.1016/s0140-6736(65)92840-0}}</ref><ref name="pmid15578369">{{Cite journal |vauthors=Weiss MM, Weiss PD, Mathisen G, Guze P |title=Rethinking smallpox |journal=Clin. Infect. Dis. |volume=39 |issue=11 |pages=1668–73 |date=December 2004|pmid=15578369 |doi=10.1086/425745 |pmc=7107961 |doi-access=free }}</ref>

The condensation of N-methyl[[isatin]] with [[thiosemicarbazide]] leads to methisazone.{{cn|date=January 2023}}

[[Category:Antiviral drugs]]

[[Category:Thiosemicarbazones]]

[[Category:Oxindoles]]