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-carboximidamide hydrochloride

• ChemBase ID: 179530
• Molecular Formular: C8H14ClN5O4
• Molecular Mass: 284.64413419
• Monoisotopic Mass: 284.09020582
• SMILES: n1c(nn(c1)[13C@H]1[13C@H]([13CH](O)[13C@@H]([13CH2]O)O1)O)C(=N)N.Cl
• Canonical SMILES: O[13CH2][13C@H]1O[13C@H]([13C@H]([13CH]1O)O)n1cnc(n1)C(=N)N.Cl
• InChI: InChI=1S/C8H13N5O4.ClH/c9-6(10)7-11-2-13(12-7)8-5(16)4(15)3(1-14)17-8;/h2-5,8,14-16H,1H2,(H3,9,10);1H/t3-,4?,5+,8-;/m1./s1/i1+1,3+1,4+1,5+1,8+1
• InChIKey: PIGYMBULXKLTCJ-AZYYQSMBSA-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-carboximidamide hydrochloride
• 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-carboximidamide hydrochloride
• Synonyms: 1-β-D-(Ribofuranosyl-13C5-1H-1,2,4-triazole-3-carboximidamide Monohydrochloride; AVS 206-13C5; ICN 3142-13C5; Ribamidine-13C5 Hydrochloride; Taribavirin-13C5 Hydrochloride; Viramidine-13C5 Hydrochloride

Database IDs

• PubChem SID: 164235440
• PubChem CID: 46783250

CALCULATED PROPERTIES

• Acid pKa: 12.420825
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.7653656
• LogD (pH = 7.4): -2.5410306
• Log P: -2.5372574
• Molar Refractivity: 77.1685 cm^3
• Polarizability: 21.263273 Å^3
• Polar Surface Area: 150.5 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V673002

Liver-targeting antiviral nucleoside analog; 3-carboxamidine prodrug of Ribavirin.

REFERENCES

• Lin, C., et al.: Antivir. Chem. Chemother., 14, 145 (2003)
• Wu, J.Z., et al.: Antimicrob. Agents Chemother., 48, 4006 (2003)
• Aora, S., et al.: J. Clin. Pharmacol., 45, 275 (2003)