Avosentan | SPP301 | RO 67-0565 | R-639 | CAS#290815-26-8 | endothelin receptor antagonist

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

MedKoo CAT#: 326692

CAS#: 290815-26-8

Description: Avosentan, also known as SPP301, R-639, and RO 67-0565, is an endothelin receptor antagonist. Avosentan ameliorates nephropathy and atherosclerosis in diabetic apolipoprotein E knockout mice. Avosentan is protective in hypertensive nephropathy at doses not causing fluid retention. Avosentan reduces albuminuria when added to standard treatment in people with type 2 diabetes and overt nephropathy but induces significant fluid overload and congestive heart failure.

Chemical Structure

Avosentan

CAS# 290815-26-8

Instruction

Theoretical Analysis

MedKoo Cat#: 326692
Name: Avosentan
CAS#: 290815-26-8
Chemical Formula: C23H21N5O5S
Exact Mass: 479.13
Molecular Weight: 479.511
Elemental Analysis: C, 57.61; H, 4.41; N, 14.61; O, 16.68; S, 6.69

Price and Availability

Size	Price	Availability
5mg	USD 285	2 Weeks
10mg	USD 485	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: SPP301; SPP301; SPP301; RO 67-0565; RO-67-0565; RO67-0565; R-639; Avosentan

IUPAC/Chemical Name: 5-methylpyridine-2-sulfonic acid (6-methoxy-5-(2-methoxyphenoxy)-2-(pyridin-4-yl)pyrimidin-4-yl)amide

InChi Key: YBWLTKFZAOSWSM-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H21N5O5S/c1-15-8-9-19(25-14-15)34(29,30)28-22-20(33-18-7-5-4-6-17(18)31-2)23(32-3)27-21(26-22)16-10-12-24-13-11-16/h4-14H,1-3H3,(H,26,27,28)

SMILES Code: O=S(C1=NC=C(C)C=C1)(NC2=NC(C3=CC=NC=C3)=NC(OC)=C2OC4=CC=CC=C4OC)=O

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 479.51 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Baltatu OC, Zaugg CE, Schumacher C, Louie P, Campos LA, Bader M. Avosentan is protective in hypertensive nephropathy at doses not causing fluid retention. Pharmacol Res. 2014 Feb;80:9-13. doi: 10.1016/j.phrs.2013.12.003. Epub 2013 Dec 22. PMID: 24368192.

2: Mann JF, Green D, Jamerson K, Ruilope LM, Kuranoff SJ, Littke T, Viberti G; ASCEND Study Group. Avosentan for overt diabetic nephropathy. J Am Soc Nephrol. 2010 Mar;21(3):527-35. doi: 10.1681/ASN.2009060593. Epub 2010 Feb 18. PMID: 20167702; PMCID: PMC2831858.

3: Wenzel RR, Littke T, Kuranoff S, Jürgens C, Bruck H, Ritz E, Philipp T, Mitchell A; SPP301 (Avosentan) Endothelin Antagonist Evaluation in Diabetic Nephropathy Study Investigators. Avosentan reduces albumin excretion in diabetics with macroalbuminuria. J Am Soc Nephrol. 2009 Mar;20(3):655-64. doi: 10.1681/ASN.2008050482. Epub 2009 Jan 14. PMID: 19144760; PMCID: PMC2653691.

4: Konieczka K, Meyer P, Schoetzau A, Neutzner A, Mozaffarieh M, Flammer J. Effect of avosentan (SPP-301) in porcine ciliary arteries. Curr Eye Res. 2011 Feb;36(2):118-24. doi: 10.3109/02713683.2010.529982. PMID: 21281066.

5: Dieterle W, Hengelage T. Absolute bioavailability and pharmacokinetics of avosentan in man. Int J Clin Pharmacol Ther. 2009 Sep;47(9):587-94. doi: 10.5414/cpp47587. PMID: 19761718.

6: Watson AM, Li J, Schumacher C, de Gasparo M, Feng B, Thomas MC, Allen TJ, Cooper ME, Jandeleit-Dahm KA. The endothelin receptor antagonist avosentan ameliorates nephropathy and atherosclerosis in diabetic apolipoprotein E knockout mice. Diabetologia. 2010 Jan;53(1):192-203. doi: 10.1007/s00125-009-1540-3. Epub 2009 Oct 28. PMID: 19862499.

7: Dieterle W, Mann J. Influence of avosentan (SPP3OI) on the pharmacokinetics of a second generation oral contraceptive containing ethinylestradiol and levonorgestrel in healthy female volunteers. Int J Clin Pharmacol Ther. 2006 Dec;44(12):668-74. doi: 10.5414/cpp44668. PMID: 17190377.

8: Smolander J, Vogt B, Maillard M, Zweiacker C, Littke T, Hengelage T, Burnier M. Dose-dependent acute and sustained renal effects of the endothelin receptor antagonist avosentan in healthy subjects. Clin Pharmacol Ther. 2009 Jun;85(6):628-34. doi: 10.1038/clpt.2009.15. Epub 2009 Mar 11. PMID: 19279566.

9: Hoekman J, Lambers Heerspink HJ, Viberti G, Green D, Mann JF, de Zeeuw D. Predictors of congestive heart failure after treatment with an endothelin receptor antagonist. Clin J Am Soc Nephrol. 2014 Mar;9(3):490-8. doi: 10.2215/CJN.07040713. Epub 2014 Jan 9. PMID: 24408122; PMCID: PMC3944766.

10: Baltatu OC, Iliescu R, Zaugg CE, Reckelhoff JF, Louie P, Schumacher C, Campos LA. Antidiuretic effects of the endothelin receptor antagonist avosentan. Front Physiol. 2012 Apr 18;3:103. doi: 10.3389/fphys.2012.00103. PMID: 22529820; PMCID: PMC3328756.

11: Egido J, Rojas-Rivera J, Mas S, Ruiz-Ortega M, Sanz AB, Gonzalez Parra E, Gomez-Guerrero C. Atrasentan for the treatment of diabetic nephropathy. Expert Opin Investig Drugs. 2017 Jun;26(6):741-750. doi: 10.1080/13543784.2017.1325872. PMID: 28468519.

12: Dieterle W, Hengelage T. Influence of food intake on the pharmacokinetics of avosentan in man. Int J Clin Pharmacol Ther. 2008 Sep;46(9):453-8. doi: 10.5414/cpp46453. PMID: 18793575.

13: Martínez-Díaz I, Martos N, Llorens-Cebrià C, Álvarez FJ, Bedard PW, Vergara A, Jacobs-Cachá C, Soler MJ. Endothelin Receptor Antagonists in Kidney Disease. Int J Mol Sci. 2023 Feb 8;24(4):3427. doi: 10.3390/ijms24043427. PMID: 36834836; PMCID: PMC9965540.

14: Kohan DE, Pollock DM. Endothelin antagonists for diabetic and non-diabetic chronic kidney disease. Br J Clin Pharmacol. 2013 Oct;76(4):573-9. doi: 10.1111/bcp.12064. PMID: 23228194; PMCID: PMC3791980.

15: Gagliardini E, Corna D, Zoja C, Sangalli F, Carrara F, Rossi M, Conti S, Rottoli D, Longaretti L, Remuzzi A, Remuzzi G, Benigni A. Unlike each drug alone, lisinopril if combined with avosentan promotes regression of renal lesions in experimental diabetes. Am J Physiol Renal Physiol. 2009 Nov;297(5):F1448-56. doi: 10.1152/ajprenal.00340.2009. Epub 2009 Aug 12. PMID: 19675181.

16: 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.

17: Stefoni S, Cianciolo G, Baraldi O, Iorio M, Angelini ML. Emerging drugs for chronic kidney disease. Expert Opin Emerg Drugs. 2014 Jun;19(2):183-99. doi: 10.1517/14728214.2014.900044. Epub 2014 May 16. PMID: 24836744.

18: Zhou Y, Chi J, Huang Y, Dong B, Lv W, Wang YG. Efficacy and safety of endothelin receptor antagonists in type 2 diabetic kidney disease: A systematic review and meta-analysis of randomized controlled trials. Diabet Med. 2021 Jan;38(1):e14411. doi: 10.1111/dme.14411. Epub 2020 Oct 9. PMID: 33000477.

19: Rabelink TJ, Kohan DE. Endothelin receptor blockade in patients with diabetic nephropathy. Contrib Nephrol. 2011;172:235-242. doi: 10.1159/000328703. Epub 2011 Aug 30. PMID: 21894003.

20: Fernández Fernández B, Elewa U, Sánchez-Niño MD, Rojas-Rivera JE, Martin- Cleary C, Egido J, Ortiz A. 2012 update on diabetic kidney disease: the expanding spectrum, novel pathogenic insights and recent clinical trials. Minerva Med. 2012 Aug;103(4):219-34. PMID: 22805616.

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