1-[(2R,3S,5R)-3,4-dihydroxy-5-[hydroxy(13C)methyl](2,3,4,5-13C4)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide

• ChemBase ID: 177511
• Molecular Formular: C8H12N4O5
• Molecular Mass: 249.16795419
• Monoisotopic Mass: 249.09754369
• SMILES: [13C@@H]1([13CH]([13C@H](O[13C@H]1n1nc(nc1)C(=O)N)[13CH2]O)O)O
• Canonical SMILES: O[13CH2][13C@H]1O[13C@H]([13C@H]([13CH]1O)O)n1cnc(n1)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/i1+1,3+1,4+1,5+1,8+1
• InChIKey: IWUCXVSUMQZMFG-ZWMFLENSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3S,5R)-3,4-dihydroxy-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
• IUPAC Traditional name: 1-[(2R,3S,5R)-3,4-dihydroxy-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
• Synonyms: 1-β-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide-13C5; Copegus-13C5; ICN 1229-13C5; MegaRibavirin-13C5; NSC 163039-13C5; Ravanex-13C5; Rebetol-13C5; Ribamide-13C5; Ribamidil-13C5; Ribasphere-13C5; Ribavarin-13C5; Tribavirin-13C5; Vilona-13C5; Viramid-13C5; Virazole-13C5; Virizadole-13C5; Ribavirin-13C5

Database IDs

• PubChem SID: 164233421
• PubChem CID: 71752066

CALCULATED PROPERTIES

• Acid pKa: 11.878701
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.7682977
• LogD (pH = 7.4): -2.7683082
• Log P: -2.7682974
• Molar Refractivity: 64.5744 cm^3
• Polarizability: 20.505037 Å^3
• Polar Surface Area: 143.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 166-168°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R414477

Labelled Rivavirin. Purine nucleoside analog; inhibits inosine monophosphate dehydrogenase (IMPDH). Used as an antiviral agent.

REFERENCES

• Fernandez, H., et al.: Eur. J. Epidemiol., 2, 1 (1986)
• Liao, H.J. and Stollar, V.: Antiviral Res., 22, 285 (1986)
• Honda, Y., et al.: Antimicrob. Agents Chemother., 38, 653 (1986)
• Reichard, O., et al.: Lancet, 351, 83 (1998)