1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboximidamide hydrochloride

• ChemBase ID: 179529
• Molecular Formular: C8H14ClN5O4
• Molecular Mass: 279.68086
• Monoisotopic Mass: 279.07343163
• SMILES: n1c(nn(c1)[C@H]1[C@H](C(O)[C@@H](CO)O1)O)C(=N)N.Cl
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)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
• InChIKey: PIGYMBULXKLTCJ-KIAAEPDXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboximidamide hydrochloride
• IUPAC Traditional name: 1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboximidamide hydrochloride
• Synonyms: 1-β-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboximidamide Monohydrochloride; AVS 206; ICN 3142; Ribamidine Hydrochloride; Taribavirin Hydrochloride; Viramidine Hydrochloride

Database IDs

• CAS Number: 40372-00-7
• PubChem SID: 164235439
• PubChem CID: 46783248

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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 167-172°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V673000

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)