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MedKoo Cat#: 584311 | Name: Methisazone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methisazone is an antiviral agent effective against pox viruses.

Chemical Structure

Methisazone
Methisazone
CAS#1910-68-5

Theoretical Analysis

MedKoo Cat#: 584311

Name: Methisazone

CAS#: 1910-68-5

Chemical Formula: C10H10N4OS

Exact Mass: 234.0575

Molecular Weight: 234.28

Elemental Analysis: C, 51.27; H, 4.30; N, 23.92; O, 6.83; S, 13.68

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
26153-15-1 (Z-isomer)
Synonym
Methisazone; Compound 33T57
IUPAC/Chemical Name
(Z)-2-(1-methyl-2-oxoindolin-3-ylidene)hydrazine-1-carbothioamide
InChi Key
DLGSOJOOYHWROO-WQLSENKSSA-N
InChi Code
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-
SMILES Code
O=C1N(C)C2=C(C=CC=C2)/C1=N/NC(N)=S
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methisazone (Marboran) is an antiviral agent that works by inhibiting mRNA and protein synthesis.
In vitro activity:
This in silico molecular docking study investigated the inhibiting role of Methisazone and the modified drugs against SARS-CoV-2 proteins: ribonucleic acid (RNA)-dependent RNA polymerase (RdRp), spike protein, papain-like protease (PlPr), and main protease (MPro). This study found that the highest binding interactions were found with the spike protein (6VYB), with the highest overall binding being observed with Mn-bound Methisazone at -8.3 kcal/mol, followed by Zn and Ca at -8.0 kcal/mol, and Fe and Mg at -7.9 kcal/mol. Reference: Int J Mol Sci. 2021 Mar 15;22(6):2977. https://pubmed.ncbi.nlm.nih.gov/33804129/
In vivo activity:
The antiviral drug methisazone (N-methylisatin beta-thiosemicarbazone) was tested for its effect on immune responses to sheep erythrocytes and on hemopoietic colony-forming cell (granulocyte-macrophage progenitor cell) responses to complete Freund's adjuvant in mice. Methisazone increased the mortality from ectromelia in adjuvant-treated animals. Reference: Antimicrob Agents Chemother. 1972 Jan;1(1):1-5. https://pubmed.ncbi.nlm.nih.gov/4670426/

Preparing Stock Solutions

The following data is based on the product molecular weight 234.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Abdelaal Ahmed Mahmoud M Alkhatip A, Georgakis M, Montero Valenzuela LR, Hamza M, Farag E, Hodgkinson J, Hosny H, Kamal AM, Wagih M, Naguib A, Yassin H, Algameel H, Elayashy M, Abdelhaq M, Younis MI, Mohamed H, Abdulshafi M, Elramely MA. Metal-Bound Methisazone; Novel Drugs Targeting Prophylaxis and Treatment of SARS-CoV-2, a Molecular Docking Study. Int J Mol Sci. 2021 Mar 15;22(6):2977. doi: 10.3390/ijms22062977. PMID: 33804129; PMCID: PMC8001373. 2. McNeill TA. Effect of methisazone and other drugs on mouse hemophoietic colony formation in vitro. Antimicrob Agents Chemother. 1972 Jan;1(1):6-11. doi: 10.1128/AAC.1.1.6. PMID: 4670431; PMCID: PMC444157. 3. Borysiewicz J, Witaliński W. Effect of N,N'-bis(methylisatin-beta-thiosemicarbazone)-2-methylpiperazine on vaccinia virus replication in vitro and in vivo. Brief report. Arch Virol. 1979;62(1):83-6. doi: 10.1007/BF01314907. PMID: 539911. 4. McNeill TA, Fleming WA, McClure SF, Killen M. Suppression of immune and hemopoietic cellular responses by methisazone. Antimicrob Agents Chemother. 1972 Jan;1(1):1-5. doi: 10.1128/AAC.1.1.1. PMID: 4670426; PMCID: PMC444156.
In vitro protocol:
1. Abdelaal Ahmed Mahmoud M Alkhatip A, Georgakis M, Montero Valenzuela LR, Hamza M, Farag E, Hodgkinson J, Hosny H, Kamal AM, Wagih M, Naguib A, Yassin H, Algameel H, Elayashy M, Abdelhaq M, Younis MI, Mohamed H, Abdulshafi M, Elramely MA. Metal-Bound Methisazone; Novel Drugs Targeting Prophylaxis and Treatment of SARS-CoV-2, a Molecular Docking Study. Int J Mol Sci. 2021 Mar 15;22(6):2977. doi: 10.3390/ijms22062977. PMID: 33804129; PMCID: PMC8001373. 2. McNeill TA. Effect of methisazone and other drugs on mouse hemophoietic colony formation in vitro. Antimicrob Agents Chemother. 1972 Jan;1(1):6-11. doi: 10.1128/AAC.1.1.6. PMID: 4670431; PMCID: PMC444157.
In vivo protocol:
1. Borysiewicz J, Witaliński W. Effect of N,N'-bis(methylisatin-beta-thiosemicarbazone)-2-methylpiperazine on vaccinia virus replication in vitro and in vivo. Brief report. Arch Virol. 1979;62(1):83-6. doi: 10.1007/BF01314907. PMID: 539911. 2. McNeill TA, Fleming WA, McClure SF, Killen M. Suppression of immune and hemopoietic cellular responses by methisazone. Antimicrob Agents Chemother. 1972 Jan;1(1):1-5. doi: 10.1128/AAC.1.1.1. PMID: 4670426; PMCID: PMC444156.
1: Teitz Y, Ronen D, Vansover A, Stematsky T, Riggs JL. Inhibition of human immunodeficiency virus by N-methylisatin-beta 4':4'-diethylthiosemicarbazone and N-allylisatin-beta-4':4'-diallythiosemicarbazone. Antiviral Res. 1994 Aug;24(4):305-14. PubMed PMID: 7993075. 2: MARSDEN JP. Case of malignant smallpox treated with compound 33T57. Br Med J. 1962 Aug 25;2(5303):524. PubMed PMID: 14470219; PubMed Central PMCID: PMC1925910. 3: Ronen D, Sherman L, Bar-Nun S, Teitz Y. N-methylisatin-beta-4',4'-diethylthiosemicarbazone, an inhibitor of Moloney leukemia virus protein production: characterization and in vitro translation of viral mRNA. Antimicrob Agents Chemother. 1987 Nov;31(11):1798-802. PubMed PMID: 3501701; PubMed Central PMCID: PMC175042. 4: BAUER DJ, STVINCENT L, KEMPE CH, DOWNIE AW. PROPHYLACTIC TREATMENT OF SMALL POX CONTACTS WITH N-METHYLISATIN BETA-THIOSEMICARBAZONE (COMPOUND 33T57, MARBORAN). Lancet. 1963 Sep 7;2(7306):494-6. PubMed PMID: 14065422. 5: Borysiewicz J, Witaliński W. Effect of N,N'-bis(methylisatin-beta-thiosemicarbazone)-2-methylpiperazine on vaccinia virus replication in vitro and in vivo. Brief report. Arch Virol. 1979;62(1):83-6. PubMed PMID: 539911. 6: McLean DM. Methisazone therapy in pediatric vaccinia complications. Ann N Y Acad Sci. 1977 Mar 4;284:118-21. PubMed PMID: 280134. 7: Rada B, Zgórniak-Nowosielska I. Site of action of N,N'-bis(methylisatin-beta-thiosemicarbazone)-2-methylpiperazine in the vaccinia virus replication cycle. Acta Virol. 1984 Sep;28(5):428-32. PubMed PMID: 6151358. 8: Zgórniak-Nowosielska I, Gatkiewicz A, Veckenstedt A, Béládi I. Effect of N, N'-bis(methylisatin-beta-thiosemicarbazone)-2-methylpiperazine against virus-induced encephalitis in mice). Acta Virol. 1980 Dec;24(6):439-44. PubMed PMID: 6111204. 9: Hermans PE, Cockerill FR 3rd. Antiviral agents. Mayo Clin Proc. 1983 Apr;58(4):217-22. Review. PubMed PMID: 6339831. 10: Tomashevskaia MF, Turkevich MM. Spectorphotometric determination of methisazone and its extraction from mixtures. Farm Zh. 1975 Mar-Apr;(2):73-5. Ukrainian. PubMed PMID: 1140365. 11: McLean DM. Vaccinia complications and methisazone therapy. Clin Infect Dis. 2006 Jun 1;42(11):1653. PubMed PMID: 16652327. 12: Lee KC, Hersey JA. Crystal modification of methisazone by grinding. J Pharm Pharmacol. 1977 Apr;29(4):249-50. PubMed PMID: 17681. 13: Borysiewicz J, Mizerski J, Pryjma J. Effect of methisazone on immune response in mice. Chemotherapy. 1977;23(4):276-81. PubMed PMID: 862459. 14: Chang TW, Snydman DR. Antiviral agents: action and clinical use. Drugs. 1979 Nov;18(5):354-76. Review. PubMed PMID: 92398. 15: Zgórniak-Nowosielska I, Cwiek D, Sławińska B. Immune response in vaccinia virus infected mice treated with N,N'-bis/methylisatin-beta-thiosemicarbazone/-2-methylpiperazine. Arch Immunol Ther Exp (Warsz). 1985;33(6):769-76. PubMed PMID: 3868962. 16: Ronen D, Nir E, Teitz Y. Effect of N-methylisatin-beta-4':4'-diethylthiosemicarbazone on intracellular Moloney leukemia virus constituents. Antiviral Res. 1985 Aug;5(4):249-54. PubMed PMID: 2412491. 17: Bauer DJ. A history of the discovery and clinical application of antiviral drugs. Br Med Bull. 1985 Oct;41(4):309-14. Review. PubMed PMID: 2996681. 18: Teitz Y, Ladizensky E, Barko N, Burstein E. Selective repression of v-abl-encoded protein by N-methylisatin-beta-4',4'-diethylthiosemicarbazone and N-allylisatin-beta-4',4'-diallylthiosemicarbazone. Antimicrob Agents Chemother. 1993 Nov;37(11):2483-5. PubMed PMID: 8285639; PubMed Central PMCID: PMC192414. 19: Schroeder C, Presber W. [Current problems in medical virology. VI. Virostatics--what we need and what we have]. Z Arztl Fortbild (Jena). 1981 Apr 1;75(7):223-9. German. PubMed PMID: 6169209. 20: Walter M, Kolarz B, Zgórniak-Nowosielska I. Evaluation of ectodermal lesions in intravenous vaccinia infected mice as a method to investigate the antiviral activity of isatin beta-thiosemicarbazone derivative (TSK VI compound). Arch Immunol Ther Exp (Warsz). 1981;29(2):187-94. PubMed PMID: 7305631.