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JN0006 Sigma-Aldrich

Draflazine

≥98% (HPLC)

Synonym: (-)-R 75,231, (-)-R 75231, (-)-R-75231, (-)-R75231, (-)-1-[2-(4-Amino-2,6-dichloro-anilino)-2-oxo-ethyl]-4-[5,5-bis(4-fluorophenyl)pentyl]piperazine-2-carboxamide, (S)-R 75,231, (S)-R 75231, (S)-R-75231, (S)-R75231, (S)-2-(Aminocarbonyl)-N-(4-amino-2,6-dichlorophenyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide, R 88,021, R 88021, R-88021, R88021

  • CAS Number 138681-29-5

  • Empirical Formula (Hill Notation) C30H33Cl2F2N5O2

  • Molecular Weight 604.52

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, DIG-DY
assay   ≥98% (HPLC)
form   powder
optical activity   [α]/D -23 to -29°, c = 0.5 in ethanol
color   white to beige
solubility   DMSO: 2 mg/mL, clear
storage temp.   room temp
InChI   1S/C30H33Cl2F2N5O2/c31-25-15-23(35)16-26(32)29(25)37-28(40)18-39-14-13-38(17-27(39)30(36)41)12-2-1-3-24(19-4-8-21(33)9-5-19)20-6-10-22(34)11-7-20/h4-11,15-16,24,27H,1-3,12-14,17-18,35H2,(H2,36,41)(H,37,40)
InChI key   IWMYIWLIESDFRZ-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Draflazine (R88021; (-)-R75231), is a potent nucleoside transporter ENT1 (SLC29A1) inhibitor with 370-fold selectivity over ENT2 (SLC29A2). R88021 exhibits 30- and 40-times higher affinity as (+)-R75231 (R88016) using calf lung membrane preparation (by [3H]R75231 & [3H]NBI displacement) and intact human erythrocytes (by [3H]NBMPR displacement), respectively. Draflazine is 20-times more potent as R88016 in enhancing adenosine potency against ADP-induced aggregation in human whole blood (IC50 = 0.5 μM vs 10 μM with 1 μM respective inhibitor), Draflazine and R75231, but not R88016, show cardioprotective efficacy against catecholamines infusion in rabbits in vivo.

Safety & Documentation

Safety Information

WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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