50924-49-7
Mizoribine
CAS: 50924-49-7
Molecular Formula: C9H13N3O6
50924-49-7 - Names and Identifiers
| Name | Mizoribine |
| Synonyms | MZR HE-69 Bredinin Bredinine Mizoribina MIZORIBINE Mizoribine Brn 4151713 BRN 4151713 Mizoribinum UNII-4JR41A10VP Mizoribine Control Mizoribina [INN-Spanish] 5-hydroxy-1-pentofuranosyl-1H-imidazole-4-carboxamide 4-carbamoyl-1-beta-d-ribofuranosyl-imidazolium-5-olate 4-Carbamoyl-1-beta-D-ribofuranosyl-imidazolium-5-olate 5-Hydroxy-1-beta-D-ribofuranosylimidazole-4-carboxamide N'-[BETA-D-RIBOFURANOSYL]-5-HYDROXYIMIDAZOLE-4-CARBOXAMIDE 5-Hydroxy-1-beta-D-ribofuranosyl-1H-imidazole-4-carboxamide 5-hydroxy-1-(beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide 1H-Imidazole-4-carboxamide, 5-hydroxy-1-beta-D-ribofuranosyl- Anhydro-4-carbamoyl-5-hydroxy-1-b-D-ribofuranosyl-imidazolium-hydroxide Anhydro-4-carbamoyl-5-hydroxy-1-beta-D-ribofuranosyl-imidazolium hydroxide |
| CAS | 50924-49-7 |
| EINECS | 637-144-4 |
| InChI | InChI=1/C9H13N3O6/c10-7(16)4-8(17)12(2-11-4)9-6(15)5(14)3(1-13)18-9/h2-3,5-6,9,13-15,17H,1H2,(H2,10,16) |
| InChIKey | HZQDCMWJEBCWBR-UUOKFMHZSA-N |
50924-49-7 - Physico-chemical Properties
| Molecular Formula | C9H13N3O6 |
| Molar Mass | 259.22 |
| Density | 1.4155 (rough estimate) |
| Melting Point | >2000C |
| Boling Point | 402.47°C (rough estimate) |
| Specific Rotation(α) | D27 -35° (c = 0.8 in H2O) |
| Flash Point | 410.9°C |
| Solubility | Soluble in water (52 mg/ml), DMSO (52 mg/ml), ethanol (<1 mg/ml), and methanol |
| Vapor Presure | 5.2E-24mmHg at 25°C |
| Appearance | Solid |
| Color | White to Off-White |
| Maximum wavelength(λmax) | ['280nm(lit.)'] |
| Merck | 14,6222 |
| pKa | 6.75(at 25℃) |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to heat |
| Refractive Index | 1.5100 (estimate) |
| MDL | MFCD00057221 |
| Use | An imidazole nucleoside immunosuppressant agent. |
| In vitro study | Mizoribine(1-50 mg/ml) was able to dose-dependently inhibit T-cell proliferation by 10-100% under all facilitator factors tested. Mizoribine causes a decrease in intracellular GTP levels, and the filling of GTP reverses its anti-malignant proliferative effect. Mizoribine dose-dependently inhibited T-cell proliferation, and the inhibition was reversible when 50mm guanosine was added to the guanine-filled nucleotide pool. Mizoribine selectively inhibits guanine nucleotide formation in pure T cells, whereas the effect of 6-mercaptopurine (6MP) appears to be more dependent on adenine nucleotide depletion. Mizoribine inhibits HCV RNA replication with an IC50 value of 100 μm. |
| In vivo study | Mizoribine (5 or 10 mg/kg) inhibits urinary albumin excretion in rats in vivo. In the rat kidney, Mizoribine (5 or 10 mg/kg) inhibited the development of Glomerulosclerosis, renal interstitial fibrosis, and macrophage infiltration. Mizoribine (5 or 10 mg/kg) increased the expression of MCP-1, OPN, and TGF-β1 mRNA in untreated Olef rats. |
50924-49-7 - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R46 - May cause heritable genetic damage R60 - May impair fertility R61 - May cause harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| RTECS | NI3980000 |
| HS Code | 29349990 |
| Toxicity | LD50 in mice (g/kg): >1.5 i.v., >2.4 i.p. (Mizuno, 1975) |
50924-49-7 - Introduction
Mizoribine is an imidazole nucleoside, an immunosuppressant, with an IC50 of about 100 μM
Last Update：2022-10-16 17:25:39
50924-49-7 - Reference Information
| Overview | Imidazolibine, also known as brebenicillin, buredinine, imidazole glycoside, and eucystin, is a kind of imidazole nucleoside isolated from the culture filtrate of the M-2166 strain of Ascomycetes isolated from the soil by the Japanese scholar Asahi Asahi. It is a metabolite that inhibits the purine synthesis pathway of nucleic acids. It is mainly used to inhibit rejection before and after kidney transplantation, it is also used for liver transplantation and autoimmune diseases. As an immunosuppressive agent, imidazoribine is related to its inhibitory effect on purine nucleotide synthesis and increase the transcriptional activity of glucocorticoid receptors. It has been used in clinical kidney transplantation in Japan since December 1991. Many clinical transplant centers in Japan have adopted mizoribine as a routine immunosuppressive drug after renal transplantation. In recent years, China has also used it as anti-rejection medicine for kidney transplantation in clinical practice. Compared with the similar drug azathioprine, mizoribine has less hepatotoxicity and bone marrow suppression. Its main adverse reactions are gastrointestinal reactions, blood system disorders and allergic symptoms, occasionally bone marrow function inhibition and acute renal failure. |
| Pharmacological action | This product is an imidazole nucleoside antimetabolic drug. Mizoribine is a prodrug and needs to be phosphorylated in cells. Its immunosuppressive mechanism is mainly through inhibiting hypoxanthine nucleotide dehydrogenase (IMPDH) and guanine nucleoside monophosphate synthase (GMP), reducing the synthesis of guanylate, reducing the synthesis of RNA and DNA, thereby inhibiting lymphocyte proliferation and inhibiting the production of antibodies, prolonging the survival time after organ transplantation, and preventing cells from entering S phase from G1 phase. Because lymphocytes cannot synthesize purines through remedial means, this product selectively inhibits its activation. In addition, this product can interfere with the expression of cytokine receptors and antagonize the activation of cytokines on lymphocytes. This product has lighter bone marrow suppression than azathioprine. The oral bioavailability is low and individual differences are large. The average peak time of blood drug concentration after oral administration is 3~4 hours. This product is widely distributed in various tissues in the body, and the concentration is higher than that in blood, especially in kidney and stomach. It is not easy to pass through the blood-brain barrier, but it can pass through the placental barrier and move a small amount to milk. It is mainly excreted through the kidney in the original form, and the clearance half-life is 2~5 hours. |
| pharmacodynamics | this product can inhibit the rejection of gastric transplantation, has the pharmacological effect of specifically inhibiting lymphocyte proliferation, inhibits the embryo cell-like transformation reaction caused by various mitotic factors, and can prolong the life of transplanted organs. By antagonizing the synthesis process of purines, the pathway from inosinic acid to uranide inhibits nucleic acid synthesis, but does not penetrate into polymer nucleic acids. |
| adverse reactions | mizoribine has myelosuppression reactions, such as leukopenia, platelets and erythrocytes. Occasionally liver damage, increased blood urea nitrogen, gastrointestinal bleeding, allergies, fever, hair removal, lung infection, glossitis, stomatitis, etc., there are also loss of appetite, nausea, vomiting, diarrhea, abdominal fullness, etc. |
| precautions | (1) for those who are allergic to this product, the white blood cell count is below 3 × 109/L, and pregnant and lactating women are prohibited. Patients with bone marrow suppression, postoperative bacterial or viral infection, bleeding tendency, liver and kidney insufficiency should be used with caution. (2) The safety of this product for children and women of childbearing age has not been established. (3) During treatment, close attention should be paid to bleeding, infection and other conditions. Blood, liver and kidney functions should be checked regularly, and the drug should be stopped or the dose adjusted according to the condition. |
| biological activity | Mizoribine (Bredinin, NSC 289637) is an imidazole nucleoside, an immunosuppressant that inhibits the replication of HCV RNA, and its anti-HCV activity The IC50 is about μM. Mizoribine is a selective inhibitor of inosine-5 '-monophosphate dehydrogenase (IMPDH) and guanosine monophosphate synthetase. Mizoribine can also inhibit SARS-CoV. |
| Target | Value |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral administration-rat LD50: 3100 mg/kg; Abdominal cavity-mouse LD50: 5000 mg/kg |
| flammability hazard characteristics | thermal decomposition discharges toxic nitrogen oxide gas |
| storage and transportation characteristics | warehouse ventilation, low temperature, drying |
| fire extinguishing agent | water, foam, sand, carbon dioxide, dry powder |
Last Update：2024-04-09 20:02:46
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Product Name: Mizoribine Visit Supplier Webpage Request for quotationCAS: 50924-49-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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