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Key Documents

JN0006

Sigma-Aldrich

Draflazine

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C30H33Cl2F2N5O2
CAS Number:
Molecular Weight:
604.52
UNSPSC Code:
12352200
NACRES:
NA.77

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

SMILES string

Fc1ccc(cc1)C(CCCCN3CC(N(CC3)CC(=O)Nc4c(cc(cc4Cl)N)Cl)C(=O)N)c2ccc(cc2)F

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

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.
Potent nucleoside transporter ENT1 (SLC29A1) inhibitor with 370-fold selectivity over ENT2 (SLC29A2) and cardioprotective efficacy in vivo.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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