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Purity: ≥98%
Methisazone (Marboran) is an antiviral agent that inhibits mRNA and protein synthesis. Methisazone is also a SARS-CoV-2 (COVID-19) inhibitor and has also been used in pox viruses.
| Targets |
mRNA/protein synthesis; antiviral; SARS-CoV-2
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|---|---|
| ln Vitro |
Methisazone is an inhibitor of protein synthesis might become convenient treatment option as well against COVID-19.[1]
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| ln Vivo |
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. Suppressive activity was demonstrated in both systems, the immune system being more readily and more consistently susceptible. Evidence is presented which suggests that the insoluble particulate form of the drug has both stimulatory and suppressive effects on the colony-forming cell system, whereas the soluble form is only suppressive. Methisazone increased the mortality from ectromelia in adjuvant-treated animals[3].
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| Enzyme Assay |
SARS-CoV-2 currently lacks effective first-line drug treatment. We present promising data from in silico docking studies of new Methisazone compounds (modified with calcium, Ca; iron, Fe; magnesium, Mg; manganese, Mn; or zinc, Zn) designed to bind more strongly to key proteins involved in replication of SARS-CoV-2. In this in silico molecular docking study, we 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). We 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. We also found that the metal-modified Methisazone had higher affinity for PlPr and MPro. In addition, we identified multiple binding pockets that could be singly or multiply occupied on all proteins tested. The best binding energy was with Mn-Methisazone versus spike protein, and the largest cumulative increases in binding energies were found with PlPr. We suggest that further studies are warranted to identify whether these compounds may be effective for treatment and/or prophylaxis[2].
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| Cell Assay |
Culture of hemopoietic colony-forming cells. [3]
Hemopoietic colony-forming cells were cultured in Nunclon 30-mm plastic dishes by use of the media and underlayer technique previously described. Bone marrow and spleen cells were suspended in collecting medium and kept at 4 C prior to culture. Counts of total cells per femur were made by removing the complete contents of a femur into 2 ml of ethylenediaminetetraacetate. Gentle pipetting after 30 min of incubation at 37 C ensured a single-cell suspension. Serum colony-stimulating activity. [3] The colonystimulating activity of serum was measured by counting the number of colonies stimulated when 0.05 ml of serum was added to cultures of 5 X 104 normal C57B1 bone marrow cells. To compare activity of different sera, all were tested in the same batch of cultures. |
| Animal Protocol |
Mice. [3]
Female C57B1 mice, 6 to 12 weeks old, were used for most experiments on cellular responses. In some confirmatory experiments, female CBA mice were used. Mice of each strain were from inbred colonies maintained in this Department. The experiments on ectromelia infection were performed on BSVS mice as our earlier studies -on ectromelia used mice of this strain. [3] Methisazone. [3] The following preparations of methisazone were used: (i) whole suspension, (ii) clarified suspension, and (iii) pure solution. The whole and clarified suspensions were prepared from commercially available sachets. The whole suspension consisted of a 1: 20 dilution of this material (10 mg/ml) in normal sterile saline. The clarified preparation was prepared from this by centrifugation (2,000 rev/min for 10 min in a bench centrifuge) and filtration of the supernatant fluid through a 220-nm membrane. The powder was dissolved in dimethylformamide (23 mg in 0.5 ml), added to 900 ml of water, and autoclaved for 10 min at 10 psi. This solution was stored at 56 C and mixed with 10 times concentrated Eagle's tissue culture medium in a ratio of one part medium to nine parts methisazone.[3] |
| References |
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| Additional Infomation |
Metisazone is a member of indoles.
Methisazone is a thiosemicarbazone with activity against poxviruses. Methisazone inhibits the synthesis of structural viral proteins and interrupts full assembly of mature virus. An antiviral agent effective against pox viruses. |
| Molecular Formula |
C10H10N4OS
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|---|---|
| Molecular Weight |
234.2776
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| Exact Mass |
234.058
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| Elemental Analysis |
C, 51.27; H, 4.30; N, 23.92; O, 6.83; S, 13.68
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| CAS # |
1910-68-5
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| Related CAS # |
26153-15-1 (Z-isomer);
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| PubChem CID |
667492
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.47 g/cm3
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| Boiling Point |
410.3ºC at 760 mmHg
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| Melting Point |
245°
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| Flash Point |
202ºC
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| Vapour Pressure |
6.07E-07mmHg at 25°C
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| Index of Refraction |
1.732
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| LogP |
1.356
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
16
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| Complexity |
309
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CN1C2C(=CC=CC=2)/C(=N\NC(=S)N)/C1=O
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| InChi Key |
TTZUCVNWOZLIGL-UHFFFAOYSA-N
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| InChi Code |
InChI:
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| Chemical Name |
(2-hydroxy-1-methylindol-3-yl)iminothiourea
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| Synonyms |
ethisazone; Metisazone; 1910-68-5; Marboran; Kemoviran; Metisazon; Metisazonum; Viruzona;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2684 mL | 21.3420 mL | 42.6840 mL | |
| 5 mM | 0.8537 mL | 4.2684 mL | 8.5368 mL | |
| 10 mM | 0.4268 mL | 2.1342 mL | 4.2684 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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