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MedKoo Cat#: 200370 | Name: Atrasentan HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Atrasentan, also known as ABT-627, is a orally available ETA receptor antagonist with potential antineoplastic activity. As a selective antagonist of the endothelin-A (ETA) receptor, atrasentan binds selectively to the ETA receptor, which may result in inhibition of endothelin-induced angiogenesis and tumor cell proliferation.

Chemical Structure

Atrasentan HCl
Atrasentan HCl
CAS#195733-43-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 200370

Name: Atrasentan HCl

CAS#: 195733-43-8 (HCl)

Chemical Formula: C29H39ClN2O6

Exact Mass: 0.0000

Molecular Weight: 547.09

Elemental Analysis: C, 63.67; H, 7.19; Cl, 6.48; N, 5.12; O, 17.55

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Related CAS #
195733-43-8 (HCl) 173937-91-2 (free base) 178738-96-0 (sodium) 195704-72-4 (free base)
Synonym
(+)A 127722; A 127722; ABT627 HCl; ABT 627 HCl; ABT-627 HCl; NSC720763; A147627; Atrasentan HCl;
IUPAC/Chemical Name
(2R,3R,4S)-4-(benzo[d][1,3]dioxol-5-yl)-1-(2-(dibutylamino)-2-oxoethyl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid hydrochloride.
InChi Key
IJFUJIFSUKPWCZ-SQMFDTLJSA-N
InChi Code
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
SMILES Code
O=C([C@H]1[C@H](C2=CC=C(OC)C=C2)N(CC(N(CCCC)CCCC)=O)C[C@@H]1C3=CC=C(OCO4)C4=C3)O.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related: 195733-43-8 (Atrasentan HCl) 173937-91-2 (Atrasentan free base). Atrasentan hydrochloride  is the orally available hydrochloride salt of pyrrolidine-3-carboxylic acid with potential antineoplastic activity. As a selective antagonist of the endothelin-A (ETA) receptor, atrasentan binds selectively to the ETA receptor, which may result in inhibition of endothelin-induced angiogenesis and tumor cell proliferation.   Atrasentan is an experimental drug that is being studied for the treatment of various types of cancer, including non-small cell lung cancer. 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.   According to http://www.hrpca.org/atrasentan.htm, [Cancer. 2007 Nov 1;110(9):1959-66.] A phase 3 randomized controlled trial of the efficacy and safety of atrasentan in men with metastatic hormone-refractory prostate cancer. Carducci MA, Saad F, brahamsson PA, Dearnaley DP, Schulman CC, North SA, Sleep DJ, Isaacson JD, Nelson JB; for the Atrasentan Phase III Study Group Institutions. Presented at the 40th Annual Meeting of the American Society of Clinical Oncology, New Orleans, Louisiana, June 5-8, 2004. The conclusion states that Atrasentan did not delay disease progression in men with metastatic HRPC despite evidence of biologic effects on PSA and BAP as markers of disease burden.    

Preparing Stock Solutions

The following data is based on the product molecular weight 547.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Smeijer JD, Koomen J, Kohan DE, McMurray JJV, Bakris GL, Correa-Rotter R, Hou FF, Januzzi JL, Kitzman DW, Kolansky DM, Makino H, Perkovic V, Tobe S, Parving HH, de Zeeuw D, Heerspink HJL. Increase in BNP in Response to Endothelin- Receptor Antagonist Atrasentan Is Associated With Incident Heart Failure. JACC Heart Fail. 2022 Jul;10(7):498-507. doi: 10.1016/j.jchf.2022.03.004. Epub 2022 May 4. PMID: 35772861. 2: Jackson AM, Benson L, Savarese G, Hage C, Jhund PS, Petrie MC, Dahlström U, McMurray JJV, Lund LH. Apparent Treatment-Resistant Hypertension Across the Spectrum of Heart Failure Phenotypes in the Swedish HF Registry. JACC Heart Fail. 2022 Jun;10(6):380-392. doi: 10.1016/j.jchf.2022.04.006. PMID: 35654522. 3: Chavez E, Rodriguez J, Drexler Y, Fornoni A. Novel Therapies for Alport Syndrome. Front Med (Lausanne). 2022 Apr 25;9:848389. doi: 10.3389/fmed.2022.848389. PMID: 35547199; PMCID: PMC9081811. 4: Stuart DC Stuart, Peterson C, Hu C, Revelo MP, Huang Y, Kohan DE, Ramkumar N. Lack of renoprotective effects of targeting the endothelin A receptor and/or sodium glucose transporter 2 in a mouse model of type 2 diabetic kidney disease. Can J Physiol Pharmacol. 2022 May 7. doi: 10.1139/cjpp-2022-0082. Epub ahead of print. PMID: 35531905. 5: Hula N, Vu J, Quon A, Kirschenman R, Spaans F, Liu R, Cooke CM, Davidge ST. Sex-specific effects of prenatal hypoxia on the cardiac endothelin system in adult offspring. Am J Physiol Heart Circ Physiol. 2022 Mar 1;322(3):H442-H450. doi: 10.1152/ajpheart.00636.2021. Epub 2022 Feb 4. PMID: 35119336. 6: Culshaw G, Binnie D, Dhaun N, Hadoke P, Bailey M, Webb DJ. The acute pressure natriuresis response is suppressed by selective ETA receptor blockade. Clin Sci (Lond). 2021 Dec 17;136(1):15–28. doi: 10.1042/CS20210937. Epub ahead of print. PMID: 34918049; PMCID: PMC8734438. 7: Ahmad N, Veerapalli H, Lankala CR, Castaneda EE, Aziz A, Rockferry AG, Hamid P. Endothelin Receptor Antagonists as a Potential Treatment of Diabetic Nephropathy: A Systematic Review. Cureus. 2021 Nov 7;13(11):e19325. doi: 10.7759/cureus.19325. PMID: 34909290; PMCID: PMC8653857. 8: Ortiz A, Fernandez-Fernandez B. Atrasentan: The Difficult Task of Integrating Endothelin A Receptor Antagonists into Current Treatment Paradigm for Diabetic Kidney Disease. Clin J Am Soc Nephrol. 2021 Dec 1;16(12):1775–8. doi: 10.2215/CJN.13601021. Epub ahead of print. PMID: 34853063; PMCID: PMC8729503. 9: Waijer SW, Gansevoort RT, Bakris GL, Correa-Rotter R, Hou FF, Kohan DE, Kitzman DW, Makino H, McMurray JJV, Perkovic V, Tobe S, Parving HH, de Zeeuw D, Heerspink HJL. The Effect of Atrasentan on Kidney and Heart Failure Outcomes by Baseline Albuminuria and Kidney Function: A Post Hoc Analysis of the SONAR Randomized Trial. Clin J Am Soc Nephrol. 2021 Dec 1;16(12):1824–32. doi: 10.2215/CJN.07340521. Epub ahead of print. PMID: 34853062; PMCID: PMC8729501. 10: Heerspink HJL, Xie D, Bakris G, Correa-Rotter R, Hou FF, Kitzman DW, Kohan D, Makino H, McMurray JJV, Perkovic V, Rossing P, Parving HH, de Zeeuw D; on behalf on the SONAR Investigators. Early Response in Albuminuria and Long-Term Kidney Protection during Treatment with an Endothelin Receptor Antagonist: A Prespecified Analysis from the SONAR Trial. J Am Soc Nephrol. 2021 Nov;32(11):2900-2911. doi: 10.1681/ASN.2021030391. Epub 2021 Sep 22. PMID: 34551995; PMCID: PMC8806086. 11: Bądzyńska B, Vaneckova I, Sadowski J, Hojná S, Kompanowska-Jezierska E. Effects of systemic and renal intramedullary endothelin-1 receptor blockade on tissue NO and intrarenal hemodynamics in normotensive and hypertensive rats. Eur J Pharmacol. 2021 Nov 5;910:174445. doi: 10.1016/j.ejphar.2021.174445. Epub 2021 Sep 4. PMID: 34492284. 12: Habib YH, Gowayed MA, Abdelhady SA, El-Deeb NM, Darwish IE, El-Mas MM. Modulation by antenatal therapies of cardiovascular and renal programming in male and female offspring of preeclamptic rats. Naunyn Schmiedebergs Arch Pharmacol. 2021 Nov;394(11):2273-2287. doi: 10.1007/s00210-021-02146-7. Epub 2021 Sep 1. PMID: 34468816. 13: Khurana N, James S, Coughlan MT, MacIsaac RJ, Ekinci EI. Novel Therapies for Kidney Disease in People With Diabetes. J Clin Endocrinol Metab. 2022 Jan 1;107(1):e1-e24. doi: 10.1210/clinem/dgab639. PMID: 34460928. 14: Waijer SW, de Vries ST, Busch R, Xie D, Gansevoort RT, Hou FF, Górriz JL, Laverman GD, De Nicola L, Pascual J, Provenzano M, Pergola PE, Tang SCW, Wanner C, Zaoui P, Parving HH, de Zeeuw D, Heerspink HJL. Large Between-Patient Variability in eGFR Decline before Clinical Trial Enrollment and Impact on Atrasentan's Efficacy: A Post Hoc Analysis from the SONAR Trial. J Am Soc Nephrol. 2021 Nov;32(11):2731-2734. doi: 10.1681/ASN.2021040498. Epub 2021 Aug 20. PMID: 34417318; PMCID: PMC8806091. 15: Docherty KF, Jhund PS, Claggett B, Ferreira JP, Bengtsson O, Inzucchi SE, Køber L, Kosiborod MN, Langkilde AM, Martinez FA, Ponikowski P, Sabatine MS, Sjöstrand M, Solomon SD, McMurray JJV; DAPA-HF Investigators and Committees. Extrapolating Long-term Event-Free and Overall Survival With Dapagliflozin in Patients With Heart Failure and Reduced Ejection Fraction: An Exploratory Analysis of a Phase 3 Randomized Clinical Trial. JAMA Cardiol. 2021 Nov 1;6(11):1298-1305. doi: 10.1001/jamacardio.2021.2632. PMID: 34319398; PMCID: PMC8576587. 16: Rivera-Gonzalez O, Wilson NA, Coats LE, Taylor EB, Speed JS. Endothelin receptor antagonism improves glucose handling, dyslipidemia, and adipose tissue inflammation in obese mice. Clin Sci (Lond). 2021 Jul 30;135(14):1773-1789. doi: 10.1042/CS20210549. PMID: 34278410; PMCID: PMC8650556. 17: Rush CJ, Berry C, Oldroyd KG, Rocchiccioli JP, Lindsay MM, Touyz RM, Murphy CL, Ford TJ, Sidik N, McEntegart MB, Lang NN, Jhund PS, Campbell RT, McMurray JJV, Petrie MC. Prevalence of Coronary Artery Disease and Coronary Microvascular Dysfunction in Patients With Heart Failure With Preserved Ejection Fraction. JAMA Cardiol. 2021 Oct 1;6(10):1130-1143. doi: 10.1001/jamacardio.2021.1825. PMID: 34160566; PMCID: PMC8223134. 18: Habib YH, Abdelhady SA, Gowayed MA, El-Deeb NM, Darwish IE, El-Mas MM. Prenatal endothelin or thromboxane receptor antagonism surpasses sympathoinhibition in improving cardiorenal malfunctions in preeclamptic rats. Toxicol Appl Pharmacol. 2021 Sep 1;426:115615. doi: 10.1016/j.taap.2021.115615. Epub 2021 Jun 6. PMID: 34102242. 19: Berillo O, Coelho SC, Mahjoub N, Offermanns S, Paradis P, Schiffrin EL. Aldosterone contributes to hypertension in male mice inducibly overexpressing human endothelin-1 in endothelium. J Hypertens. 2021 Sep 1;39(9):1908-1917. doi: 10.1097/HJH.0000000000002880. Erratum in: J Hypertens. 2021 Nov 1;39(11):2333. PMID: 34039912. 20: Smeijer JD, Kohan DE, Webb DJ, Dhaun N, Heerspink HJL. Endothelin receptor antagonists for the treatment of diabetic and nondiabetic chronic kidney disease. Curr Opin Nephrol Hypertens. 2021 Jul 1;30(4):456-465. doi: 10.1097/MNH.0000000000000716. PMID: 33990507.