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Antiviral API
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Mitoguazone
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| Category | Human immunodeficiency Virus (HIV) |
| CAS | 459-86-9 |
| Description | Mitoguazone is a guanylhydrazone with potential antineoplastic activity. Mitoguazone competitively inhibits S-adenosyl-L-methionine decarboxylase (SAMD), an enzyme involved in the synthesis of polyamines, resulting in decreased proliferation of tumor cells, antimitochondrial effects, and p53-independent apoptosis. Polyamines, specifically spermine and spermidine, are essential for thymidine kinase production, DNA synthesis, and cell proliferation. |
Product Information
| Synonyms | MeGAG; methyl-G; methyl-GAG; MGBG; MGGH; DRG-0223; DRG 0223; DRG0223; NSC32946; NSC 32946; NSC-32946 |
| IUPAC Name | 2-[(E)-[(1E)-1-(diaminomethylidenehydrazinylidene)propan-2-ylidene]amino]guanidine |
| Molecular Weight | 184.21 |
| Molecular Formula | C5H12N8 |
| Canonical SMILES | CC(=NN=C(N)N)C=NN=C(N)N |
| InChI | InChI=1S/C5H12N8/c1-3(11-13-5(8)9)2-10-12-4(6)7/h2H,1H3,(H4,6,7,12)(H4,8,9,13)/b10-2+,11-3+ |
| InChIKey | MXWHMTNPTTVWDM-NXOFHUPFSA-N |
| Boiling Point | 323.8±25.0 °C at 760 mmHg |
| Melting Point | 256-257°C |
| Flash Point | 217.8°C |
| Purity | 99.38% |
| Density | 1.55±0.1 g/cm3 |
| Solubility | In vitro: 10 mM in DMSO |
| Appearance | Light brown to brown (Solid) |
| Storage | 4°C, sealed storage, away from moisture * In solvent : -80°C, 6 months -20°C, 1 month (sealed storage, away from moisture) |
| Complexity | 264 |
| Exact Mass | 184.11849242 |
| Index Of Refraction | 1.692 |
| In Vitro | Mitoguazone competitively inhibits spermidine synthesis in lymphocytes at concentrations as low as 0.5 μg/mL. Levels of 30 μg/mL or more inhibit protein synthesis and mitochondrial respiration. The ability of Mitoguazone to induce Apoptosis by inhibiting the polyamine pathway is assessed in three Burkitt's lymphoma cell lines (Raji, Ramos and Daudi) and one prostate carcinoma cell line (MPC 3). Mitoguazone induces Apoptosis in all the different human cancer cell lines tested in a concentration- and time-dependent way, and triggers a p53-independent programmed cell death in the human breast cancer MCF7 cell line. |
| In Vivo | The influence of different stages of leukemia P388 on the pharmacokinetics of the antineoplastic agent Mitoguazone in mice is investigated. Independent of the tumor stage investigated, the total clearance of mitoguazone is slightly reduced reflecting a moderate increase of AUC in the serum of leukemia-bearing animals. Furthermore, in an advanced tumor stage the drug levels in kidneys, liver, spleen and serum are found to be elevated to some extent in comparison to tumor-free controls in contrast to an earlier stage of leukemia. |
| PSA | 148.52000 |
| Target | HIV; Apoptosis |
| Vapor Pressure | 7.99E-08mmHg at 25°C |
| XLogP3-AA | -2.2 |
