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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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5 MG
$100.00
25 MG
$406.00

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Available to ship onApril 01, 2025Details

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5 MG
$100.00
25 MG
$406.00

About This Item

Empirical Formula (Hill Notation):
C30H33Cl2F2N5O2
CAS Number:
138681-29-5
Molecular Weight:
604.52
UNSPSC Code:
12352200
NACRES:
NA.77

$100.00

Available to ship onApril 01, 2025Details

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000321772
0000321772

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H Van Belle et al.
Cardiovascular research, 27(1), 111-115 (1993-01-01)
R 75,231, a potent and specific nucleoside transport inhibitor, largely prevents cardiac damage and death in catecholamine challenged rabbits. The major biochemical effect of nucleoside transport inhibition in ischaemic and reperfused myocardium is a prolonged accumulation of adenosine. The cardioprotection
Nucleoside and nucleobase transport systems of mammalian cells.
D A Griffith et al.
Biochimica et biophysica acta, 1286(3), 153-181 (1996-10-29)
M W Beukers et al.
European journal of pharmacology, 266(1), 57-62 (1994-01-01)
In this study, we determined whether R75231, (+/-)-2-(aminocarbonyl)-N-(4-amino-2,6-dichlorophenyl)-4-[5,5-bis( 4-fluoro- phenyl)pentyl]-1-piperazineacetamide, and its two enantiomers, all nucleoside transport inhibitors, could play a role as anti-aggregatory agents. First, we determined the binding characteristics of [3H]nitrobenzylthioinosine, also a nucleoside transport inhibitor, on intact
A P IJzerman et al.
Naunyn-Schmiedeberg's archives of pharmacology, 345(5), 558-563 (1992-05-01)
The tritiated analogue of R75231 ((+-)-2-(aminocarbonyl)-N-(4-amino-2,6-dichlorophenyl)-4-[5,5-bis (4-fluorophenyl)pentyl]-1-piperazineacetamide) has been examined as a new radioligand for (nitrobenzylthioinosine sensitive) nucleoside transport proteins. [3H]R75231 was prepared in two steps from R69064 ((+-)-4-[5,5-bis[4-fluorophenyl)-4-pentenyl]-2-piperazinecarboxamide+ ++ dihydrochloride) with a specific activity of 0.23 TBq/mmol (6.3 Ci/mmol).
J R Hammond
Naunyn-Schmiedeberg's archives of pharmacology, 361(4), 373-382 (2000-04-14)
The equilibrative nucleoside transporters of mammalian cells play an important role in the regulation of extracellular adenosine concentrations, and inhibition of these transporters potentiates the biological effects of adenosine. Two subtypes of equilibrative transporters have been defined by their differential

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