Atrasentan

Title: Atrasentan
CAS Registry Number: 173937-91-2
CAS Name: (2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)-3-pyrrolidinecarboxylic acid
Additional Names: trans,trans-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-1-[[(dibutylamino)carbonyl]methyl]pyrrolidine-3-carboxylic acid
Manufacturers' Codes: (+)-A-127722
Molecular Formula: C29H38N2O6
Molecular Weight: 510.62
Percent Composition: C 68.21%, H 7.50%, N 5.49%, O 18.80%
Literature References: Endothelin (ET) antagonist with selectivity for the ETA subtype. Prepn: M. Winn et al., WO 9606905; eidem, US 5767144 (1996, 1998 both to Abbott); eidem, J. Med. Chem. 39, 1039 (1996). Synthesis: S. J. Wittenberger, M. A. McLaughlin, Tetrahedron Lett. 40, 7175 (1999). HPLC determn in pharmaceutical formulations: J. A. Morley et al., J. Pharm. Biomed. Anal. 19, 777 (1999); in plasma: P. D. Bryan et al., Biomed. Chromatogr. 15, 525 (2001). In vitro inhibition of ovarian carcinoma: D. Salani et al., Clin. Sci. 103, Suppl. 48, 318S (2002). Clinical pharmacokinetics and dynamics: M. C. Verhaar et al., Br. J. Clin. Pharmacol. 49, 562 (2000); and safety: M. A. Carducci et al., J. Clin. Oncol. 20, 2171 (2002). Clinical evaluation in prostate cancer: M. Fisher, Clin. Prostate Cancer 1, 79 (2002). Review of clinical development in prostate cancer: A. Jimeno, M. Carducci, Expert Opin. Invest. Drugs 13, 1631-1640 (2004).
Properties: mp 122-124°.
Melting point: mp 122-124°
Derivative Type: Hydrochloride
CAS Registry Number: 195733-43-8
Manufacturers' Codes: ABT-627; A-147627.1
Trademarks: Xinlay (Abbott)
Molecular Formula: C29H38N2O6.HCl
Molecular Weight: 547.08
Percent Composition: C 63.67%, H 7.19%, N 5.12%, O 17.55%, Cl 6.48%
Properties: Crystalline, non-hygroscopic solid. Readily sol in water.
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Endothelin Receptor Antagonist.
Atrazine Atrial Natriuretic Peptide Atrolactamide Atrolactic Acid Atropic Acid

Atrasentan
Atrasentan.svg
Systematic (IUPAC) name
(2R,3R,4S)-4-(1,3-benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid
Clinical data
Legal status  ?
Identifiers
CAS number 173937-91-2 N
ATC code None
PubChem CID 159594
ChemSpider 140321 YesY
UNII V6D7VK2215 YesY
ChEMBL CHEMBL9194 YesY
Chemical data
Formula C29H38N2O6 
Mol. mass 510.621 g/mol
 N (what is this?)  (verify)

Atrasentan is an experimental drug that is being studied for the treatment of various types of cancer,[1] including non-small cell lung cancer.[2]

It is an endothelin receptor antagonist selective for subtype A (ETA). While other drugs of this type (sitaxentan, ambrisentan) exploit the vasoconstrictive properties of endothelin and are mainly used for the treatment of pulmonary arterial hypertension, atrasentan blocks endothelin induced cell proliferation.