| Synonyms |
1-b-D-ribafuranosyl-1H-1,2,4-triazole-3-carboxamide; MegaRibavirin; NSC 163039; Ravanex; Rebetol; Ribamide; Ribamidil; Ribasphere; Ribavarin; Tribavirin; Vilona; Viramid; Virazole; Virizadole; 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxamide |
| IUPAC Name |
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide |
| Molecular Weight |
244.20 |
| Molecular Formula |
C8H12N4O5 |
| Canonical SMILES |
C1=NC(=NN1C2C(C(C(O2)CO)O)O)C(=O)N |
| InChI |
InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1 |
| InChIKey |
IWUCXVSUMQZMFG-AFCXAGJDSA-N |
| Boiling Point |
639.8°C at 760 mmHg |
| Melting Point |
174-176°C |
| Flash Point |
340.7±34.3 °C |
| Purity |
≥95% |
| Density |
2.08 g/cm3 |
| Solubility |
Soluble in DMF, DMSO |
| Appearance |
White Crystalline Powder |
| Storage |
Store at -20°C |
| Animal Admin |
The in vivo efficacy experiments are largely performed, using a dengue viremia model in AG129 mouse (defective of both type I and type II interferon receptors). The mice are challenged with DENV (serotype 2, TSV01 strain), at 5 × 106 pfu/mouse via i.p. injection. Imino sugars are dosed twice daily at 12 hr intervals, and ribavirin is dosed once daily, for 3 consecutive days post-infection. Blood samples are drawn 3 days post-infection for determination of plasma virus titer by plaque assay. |
| Complexity |
304 |
| Exact Mass |
244.08076950 |
| Index Of Refraction |
1.823 |
| In Vitro |
Ribavirin (5, 10 and 20 μM) does not produce any significant effect on neither cell viability nor nitrites level in non-stimulated microglia. Treatmentof LPS-stimulated microglia with 5, 10 and 20 μM Ribavirin induces reduction of NO2 levels for 43% (p<0.05), 53% (p<0.05) and 59% (p<0.05), respectively. Ribavirin (10 mM) insignificantly decreases the cell surface area in non-stimulated culture, but significantly reduces cell surface area (by 32%, p<0.05) in LPS-stimulated microglia. Ribavirin is active against DENV, with an EC50 of 3 μM in A549 cells, and combination of CM-10-18 with ribavirin demonstrates a clear enhancement in the reduction of virus replication. |
| In Vivo |
ALT, AST activities and bilirubin levels are significantly loared by administration of JAT in combination with interferon and ribavirin (p<0.01). JAT, interferon or ribavirin alone with CCl4, livers appear to exhibit some liver protection against CCl4 as evident by the presence of normal hepatic cords. Groups treated with JAT, Peg-interferon and ribavirin separately or in combination shows reduction in the expression of TGF-β and Bax. In the group treated by triple combination of interferon, ribavirin, and JAT, the expression level of p53 is markedly reduced. Ribavirin (40 mg/kg, p.o.) significantly improves the antiviral efficacy of CM-10-18 in mice. Ribavirin inhibits DENV virus infection in cultured cells, but it is ineffective in reducing viremia in monotherapy. |
| PSA |
143.72000 |
| Target |
HCV; RSV; Orthopoxvirus; Antibiotic |
| Vapor Pressure |
0.0±2.0 mmHg at 25°C |
| XLogP3-AA |
-1.8 |
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