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Sigma-Aldrich

Atrasentan hydrochloride

≥98% (HPLC)

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Synonym(s):
(2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)-3-pyrrolidinecarboxylic acid hydrochloride, 2R-(4-Methoxyphenyl)-4S-(1,3-benzodioxol-5-yl)-1-(N, N-di(n-butyl)aminocarbonyl-methyl)-pyrrolidine-3R-carboxylic acid hydrochloride, A-147627 hydrochloride, ABT-627 hydrochloride
Empirical Formula (Hill Notation):
C29H38N2O6 · HCl
CAS Number:
195733-43-8
Molecular Weight:
547.08
MDL number:
MFCD13194884
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

[H]Cl.CCCCN(CCCC)C(CN1C[C@H](C2=CC=C(OCO3)C3=C2)[C@@H](C(O)=O)[C@@H]1C4=CC=C(OC)C=C4)=O

InChI

1S/C29H38N2O6.ClH/c1-4-6-14-30(15-7-5-2)26(32)18-31-17-23(21-10-13-24-25(16-21)37-19-36-24)27(29(33)34)28(31)20-8-11-22(35-3)12-9-20;/h8-13,16,23,27-28H,4-7,14-15,17-19H2,1-3H3,(H,33,34);1H/t23-,27-,28+;/m1./s1

InChI key

IJFUJIFSUKPWCZ-SQMFDTLJSA-N

Related Categories

General description

Atrasentan has also been used to treat cardiovascular disease.

Biochem/physiol Actions

Atrasentan is a selective endothelin ETA receptor antagonist with an IC50 of 0.2 nM for ETA compared to 190 nM for ETB receptors. It blocks blocks endothelin induced cell proliferation, and has been investigated as a possible treatment for prostate cancer, and more recently for therapy for diabetic kidney disease.

WGK

WGK 3

Certificates of Analysis (COA)

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Margien G S Boels et al.
Diabetes, 65(8), 2429-2439 (2016-05-22)
Atrasentan, a selective endothelin A receptor antagonist, has been shown to reduce albuminuria in type 2 diabetes. We previously showed that the structural integrity of a glomerular endothelial glycocalyx is required to prevent albuminuria. Therefore we tested the potential of
Carmen De Miguel et al.
Scientific reports, 7, 43152-43152 (2017-02-24)
Endothelin-1 (ET-1) promotes renal damage during cardiovascular disease; yet, the molecular mechanisms involved remain unknown. Endoplasmic reticulum (ER) stress, triggered by unfolded protein accumulation in the ER, contributes to apoptosis and organ injury. These studies aimed to determine whether the
Determination of atrasentan by high performance liquid chromatography with fluorescence detection in human plasma.
Bryan P D, et al.
Biomedical Chromatography, 15(8), 525-533 (2001)
Chunhua Jin et al.
The Journal of pharmacology and experimental therapeutics, 351(2), 467-473 (2014-09-06)
Experiments determined whether the combination of endothelin A (ETA) receptor antagonist [ABT-627, atrasentan; (2R,3R,4S)-4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid] and a thiazide diuretic (chlorthalidone) would be more effective at lowering blood pressure and reducing renal injury in a rodent model of metabolic syndrome compared

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