1-{6-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-2-yl}-N-methyl-1H-pyrazole-4-carboxamide

• ChemBase ID: 177337
• Molecular Formular: C15H18N8O5
• Molecular Mass: 390.35402
• Monoisotopic Mass: 390.14001572
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)n1cc(cn1)C(=O)NC)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc2c1nc(nc2N)n1ncc(c1)C(=O)NC
• InChI: InChI=1S/C15H18N8O5/c1-17-13(27)6-2-19-23(3-6)15-20-11(16)8-12(21-15)22(5-18-8)14-10(26)9(25)7(4-24)28-14/h2-3,5,7,9-10,14,24-26H,4H2,1H3,(H,17,27)(H2,16,20,21)/t7-,9?,10+,14-/m1/s1
• InChIKey: LZPZPHGJDAGEJZ-DHRRVFGLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{6-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-2-yl}-N-methyl-1H-pyrazole-4-carboxamide
• IUPAC Traditional name: 1-{6-amino-9-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl}-N-methylpyrazole-4-carboxamide
• Synonyms: Regadenoson; 2-[4-[(Methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine

Database IDs

• CAS Number: 313348-27-5
• PubChem SID: 164233247
• PubChem CID: 71751956

CALCULATED PROPERTIES

• Acid pKa: 12.370096
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.2520862
• LogD (pH = 7.4): -2.252048
• Log P: -2.252043
• Molar Refractivity: 95.4784 cm^3
• Polarizability: 35.725533 Å^3
• Polar Surface Area: 186.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 194-196°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R142800

A selective A2A adenosine receptor agonist in myocardial imaging.

REFERENCES

• Palle, V.P., et al.: J. A. Drug Dev. Res., 50, 64 (2000)
• Gordi, T., et al.: J. Clin. Pharmacol., 47, 825 (2000)
• Zhao, G., et al.: J. Cardiovas. Pharmacol., 52, 467 (2000)
• Botvinick, E., et al.: J. Nuc. Med. Technol., 37, 14 (2000)