WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200370
CAS#: 195733-43-8 (HCl)
Description: 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.
MedKoo Cat#: 200370
Name: Atrasentan HCl
CAS#: 195733-43-8 (HCl)
Chemical Formula: C29H39ClN2O6
Exact Mass:
Molecular Weight: 547.09
Elemental Analysis: C, 63.67; H, 7.19; Cl, 6.48; N, 5.12; O, 17.55
Related CAS #: 195733-43-8 (HCl) 173937-91-2 (free base)
Synonym: (+)A 127722; A 127722; ABT627; ABT 627; ABT-627; NSC720763; A147627; Abbott 147627; US brand name: Xinlay;
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
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.
| 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: Ritter C, Zhang S, Finch JL, Liapis H, Suarez E, Ferder L, Delmez J, Slatopolsky E. Cardiac and renal effects of atrasentan in combination with enalapril and paricalcitol in uremic rats. Kidney Blood Press Res. 2014;39(4):340-52. doi: 10.1159/000355811. Epub 2014 Sep 19. PubMed PMID: 25300759; PubMed Central PMCID: PMC4225010.
2: Vaněčková I, Dobešová Z, Kuneš J, Vernerová Z, Zicha J. Endothelin A receptor blocker atrasentan lowers blood pressure by the reduction of nifedipine-sensitive calcium influx in Ren-2 transgenic rats fed a high-salt diet. J Hypertens. 2015 Jan;33(1):161-9. doi: 10.1097/HJH.0000000000000357. PubMed PMID: 25255392.
3: de Zeeuw D, Coll B, Andress D, Brennan JJ, Tang H, Houser M, Correa-Rotter R, Kohan D, Lambers Heerspink HJ, Makino H, Perkovic V, Pritchett Y, Remuzzi G, Tobe SW, Toto R, Viberti G, Parving HH. The endothelin antagonist atrasentan lowers residual albuminuria in patients with type 2 diabetic nephropathy. J Am Soc Nephrol. 2014 May;25(5):1083-93. doi: 10.1681/ASN.2013080830. Epub 2014 Apr 10. PubMed PMID: 24722445; PubMed Central PMCID: PMC4005314.
4: Younis IR, George DJ, McManus TJ, Hurwitz H, Creel P, Armstrong AJ, Yu JJ, Bacon K, Hobbs G, Peer CJ, Petros WP. Clinical pharmacology of an atrasentan and docetaxel regimen in men with hormone-refractory prostate cancer. Cancer Chemother Pharmacol. 2014 May;73(5):991-7. doi: 10.1007/s00280-014-2432-x. Epub 2014 Mar 12. PubMed PMID: 24619498; PubMed Central PMCID: PMC4010098.
5: Goldkorn A, Ely B, Quinn DI, Tangen CM, Fink LM, Xu T, Twardowski P, Van Veldhuizen PJ, Agarwal N, Carducci MA, Monk JP 3rd, Datar RH, Garzotto M, Mack PC, Lara P Jr, Higano CS, Hussain M, Thompson IM Jr, Cote RJ, Vogelzang NJ. Circulating tumor cell counts are prognostic of overall survival in SWOG S0421: a phase III trial of docetaxel with or without atrasentan for metastatic castration-resistant prostate cancer. J Clin Oncol. 2014 Apr 10;32(11):1136-42. doi: 10.1200/JCO.2013.51.7417. Epub 2014 Mar 10. PubMed PMID: 24616308; PubMed Central PMCID: PMC3970171.
6: Taneja SS. Re: docetaxel and atrasentan versus docetaxel and placebo for men with advanced castration-resistant prostate cancer (SWOG S0421): a randomised phase 3 trial. J Urol. 2014 Mar;191(3):656. doi: 10.1016/j.juro.2013.11.085. Epub 2013 Nov 28. PubMed PMID: 24522033.
7: Atrasentan of no benefit to men with metastatic prostate cancer. Bonekey Rep. 2014 Jan 15;3:503. doi: 10.1038/bonekey.2013.237. eCollection 2014 Jan 15. PubMed PMID: 24466420; PubMed Central PMCID: PMC3899568.
8: Quinn DI, Tangen CM, Hussain M, Lara PN Jr, Goldkorn A, Moinpour CM, Garzotto MG, Mack PC, Carducci MA, Monk JP, Twardowski PW, Van Veldhuizen PJ, Agarwal N, Higano CS, Vogelzang NJ, Thompson IM Jr. Docetaxel and atrasentan versus docetaxel and placebo for men with advanced castration-resistant prostate cancer (SWOG S0421): a randomised phase 3 trial. Lancet Oncol. 2013 Aug;14(9):893-900. doi: 10.1016/S1470-2045(13)70294-8. Epub 2013 Jul 17. PubMed PMID: 23871417; PubMed Central PMCID: PMC4277263.
9: Wan KX, Reimer MT, Metchkarova MP, Richter AJ, Paramadilok A, Kavetskaia O, El-Shourbagy T. Toxicokinetic evaluation of atrasentan in mice utilizing serial microsampling: validation and sample analysis in GLP study. Bioanalysis. 2012 Jun;4(11):1351-61. doi: 10.4155/bio.12.91. PubMed PMID: 22720653.
10: Andress DL, Coll B, Pritchett Y, Brennan J, Molitch M, Kohan DE. Clinical efficacy of the selective endothelin A receptor antagonist, atrasentan, in patients with diabetes and chronic kidney disease (CKD). Life Sci. 2012 Oct 15;91(13-14):739-42. doi: 10.1016/j.lfs.2012.01.011. Epub 2012 Feb 2. PubMed PMID: 22326504.
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.
