(1S,2S,3R,5S)-3-(7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-[(2H7)propylsulfanyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

• ChemBase ID: 178638
• Molecular Formular: C23H28F2N6O4S
• Molecular Mass: 522.5680264
• Monoisotopic Mass: 522.18608085
• SMILES: c1c(c(cc(c1)[C@H]1[C@@H](C1)Nc1nc(nc2c1nnn2[C@@H]1C[C@@H]([C@H]([C@H]1O)O)OCCO)SCCC)F)F
• Canonical SMILES: CCCSc1nc(N[C@@H]2C[C@H]2c2ccc(c(c2)F)F)c2c(n1)n(nn2)[C@@H]1C[C@@H]([C@H]([C@H]1O)O)OCCO
• InChI: InChI=1S/C23H28F2N6O4S/c1-2-7-36-23-27-21(26-15-9-12(15)11-3-4-13(24)14(25)8-11)18-22(28-23)31(30-29-18)16-10-17(35-6-5-32)20(34)19(16)33/h3-4,8,12,15-17,19-20,32-34H,2,5-7,9-10H2,1H3,(H,26,27,28)/t12-,15+,16+,17-,19-,20+/m0/s1
• InChIKey: OEKWJQXRCDYSHL-FNOIDJSQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,5S)-3-(7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-[(^2H₇)propylsulfanyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
• IUPAC Traditional name: (1S,2S,3R,5S)-3-(7-{[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino}-5-[(^2H₇)propylsulfanyl]-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
• Synonyms: (1S,2S,3R,5S)-3-[7-[[(1R,2S)-2-(3,4-D1,2-Cyclopentanediolifluorophenyl)cyclopropyl]amino]-5-(propylthio-d7)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)-1,2-cyclopentanediol; AR-C 126532XX-d7; AZD 6140-d7; Ticagrelor-d7

Database IDs

• PubChem SID: 164234548
• PubChem CID: 71752570

CALCULATED PROPERTIES

• Acid pKa: 12.944779
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 2.2786
• LogD (pH = 7.4): 2.2786658
• Log P: 2.278668
• Molar Refractivity: 142.1332 cm^3
• Polarizability: 49.540337 Å^3
• Polar Surface Area: 138.44 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T437702

Labelled Ticagrelor (T437700), the first reversible oral P2Y12 receptor antagonist, provides faster, greater, and more consistent ADP-receptor inhibition than Clopidogrel. Used in the treatment of acute coronary syndromes (ACS).

REFERENCES

• Matetzky, S., et al.: Circulation, 109, 3171 (2004)
• Bassand, J., et al.: Eur. Heart J., 28, 1598 (2004)
• Jakubowski, J., et al.: Cardiovasc. Drug Rev., 25, 357 (2004)