1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide

• ChemBase ID: 106043
• Molecular Formular: C8H12N4O5
• Molecular Mass: 244.20468
• Monoisotopic Mass: 244.0807695
• SMILES: NC(=O)c1nn(cn1)C1OC(CO)C(O)C1O
• Canonical SMILES: OCC1OC(C(C1O)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)
• InChIKey: IWUCXVSUMQZMFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide
• IUPAC Traditional name: ribavirin; @ribavirin
• Synonyms: 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide; 1-β-D-Ribofuranosyl-1,2,4-triazole-3-caroxamide; RIBAVIRIN

Database IDs

• CAS Number: 36791-04-5
• MDL Number: MFCD01544655
• PubChem SID: 162087271
• PubChem CID: 5064

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

• Melting Point: 173°C
• Hydrophobicity(logP): -2.849

Safety Information

• Storage Condition: 2-8°C
• RTECS: XZ4250000

Product Information

• Purity: 95%

DETAILS

MP Biomedicals - 02196066

A general antiviral reported to be active against RSV, HIV, HCV, and other infectious agents. Its metabolite, ribavirin-5'-phosphate, inhibits inosine monophosphate (IMP) dehydrogenase.

REFERENCES

• Honda, Y., et al., Antimicrob. Agents Chemother., 38: 653, (1994).
• Liao, H.J. and Stollar, V.,Antiviral Res., 22: 285, (1993).