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MedKoo Cat#: 326693 | Name: Darusentan
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Description:

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

Darusentan, also known as Lu 135252 and HMR-4005, is an Endothelin-1 receptor A inhibitor for the potential treatment of uncontrolled hypertension and cancer. Darusentan is a potent inhibitor of endothelin signaling and function in both large and small arteries. Endothelin ETA receptor blockade with darusentan increases sodium and potassium excretion in aging rats.

Chemical Structure

Darusentan
Darusentan
CAS#171714-84-4

Theoretical Analysis

MedKoo Cat#: 326693

Name: Darusentan

CAS#: 171714-84-4

Chemical Formula: C22H22N2O6

Exact Mass: 410.1478

Molecular Weight: 410.43

Elemental Analysis: C, 64.38; H, 5.40; N, 6.83; O, 23.39

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
50mg USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Lu 135252; Lu-135252; Lu135252; HMR-4005; HMR 4005; HMR4005; Darusentan
IUPAC/Chemical Name
(S)-2-((4,6-Dimethoxy-2-pyrimidinyl)oxy)-3-methoxy-3,3-diphenylpropionic acid
InChi Key
FEJVSJIALLTFRP-LJQANCHMSA-N
InChi Code
InChI=1S/C22H22N2O6/c1-27-17-14-18(28-2)24-21(23-17)30-19(20(25)26)22(29-3,15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1
SMILES Code
O=C(O)[C@@H](OC1=NC(OC)=CC(OC)=N1)C(C2=CC=CC=C2)(OC)C3=CC=CC=C3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 410.43 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: Bahde R, Kapoor S, Viswanathan P, Spiegel HU, Gupta S. Endothelin-1 receptor A blocker darusentan decreases hepatic changes and improves liver repopulation after cell transplantation in rats. Hepatology. 2014 Mar;59(3):1107-17. doi: 10.1002/hep.26766. Epub 2014 Jan 16. PubMed PMID: 24114775; PubMed Central PMCID: PMC3943745. 2: Johnson NP, Gould KL. Physiology of endothelin in producing myocardial perfusion heterogeneity: a mechanistic study using darusentan and positron emission tomography. J Nucl Cardiol. 2013 Oct;20(5):835-44. doi: 10.1007/s12350-013-9756-5. Epub 2013 Jul 11. PubMed PMID: 23842710; PubMed Central PMCID: PMC3779022. 3: Gu J, Shi X, Du Y, Wang W, Du X, Zhang L. Determination of darusentan enantiomers in rat plasma by enantioselective liquid chromatography with tandem mass spectrometry using cellulose-based chiral stationary phase. J Sep Sci. 2011 Oct;34(19):2680-5. doi: 10.1002/jssc.201100433. Epub 2011 Aug 8. PubMed PMID: 21823235. 4: Bakris GL, Lindholm LH, Black HR, Krum H, Linas S, Linseman JV, Arterburn S, Sager P, Weber M. Divergent results using clinic and ambulatory blood pressures: report of a darusentan-resistant hypertension trial. Hypertension. 2010 Nov;56(5):824-30. doi: 10.1161/HYPERTENSIONAHA.110.156976. Epub 2010 Oct 4. PubMed PMID: 20921430. 5: Liang F, Glascock CB, Schafer DL, Sandoval J, Cable L, Melvin L Jr, Hartman JC, Pitts KR. Darusentan is a potent inhibitor of endothelin signaling and function in both large and small arteries. Can J Physiol Pharmacol. 2010 Aug;88(8):840-9. doi: 10.1139/Y10-061. PubMed PMID: 20725142. 6: Enseleit F, Lüscher TF, Ruschitzka F. Darusentan, a selective endothelin A receptor antagonist, for the oral treatment of resistant hypertension. Ther Adv Cardiovasc Dis. 2010 Aug;4(4):231-40. doi: 10.1177/1753944710373785. Epub 2010 Jul 26. Review. PubMed PMID: 20660536. 7: Hartman JC, Brouwer K, Mandagere A, Melvin L, Gorczynski R. Evaluation of the endothelin receptor antagonists ambrisentan, darusentan, bosentan, and sitaxsentan as substrates and inhibitors of hepatobiliary transporters in sandwich-cultured human hepatocytes. Can J Physiol Pharmacol. 2010 Jun;88(6):682-91. doi: 10.1139/Y10-060. PubMed PMID: 20628435. 8: Enseleit F, Ruschitzka F. Darusentan in resistant hypertension: lost in translation. Curr Hypertens Rep. 2010 Feb;12(1):1-3. doi: 10.1007/s11906-009-0081-y. PubMed PMID: 20425150. 9: Bakker SJ, Gans RO, Navis G. Dietary alkalinization and darusentan for prevention of decline in glomerular filtration rate in rats fed a casein diet. Kidney Int. 2008 Dec;74(12):1625-6; author reply 1626-7. doi: 10.1038/ki.2008.434. PubMed PMID: 19034308. 10: Enseleit F, Lüscher TF, Ruschitzka F. Darusentan: a new perspective for treatment of resistant hypertension? Expert Opin Investig Drugs. 2008 Aug;17(8):1255-63. doi: 10.1517/13543784.17.8.1255 . Review. PubMed PMID: 18616421. 11: Epstein BJ. Efficacy and safety of darusentan: a novel endothelin receptor antagonist. Ann Pharmacother. 2008 Jul;42(7):1060-9. doi: 10.1345/aph.1L024. Epub 2008 Jun 3. PubMed PMID: 18523233. 12: Black HR, Bakris GL, Weber MA, Weiss R, Shahawy ME, Marple R, Tannoury G, Linas S, Wiens BL, Linseman JV, Roden R, Gerber MJ. Efficacy and safety of darusentan in patients with resistant hypertension: results from a randomized, double-blind, placebo-controlled dose-ranging study. J Clin Hypertens (Greenwich). 2007 Oct;9(10):760-9. PubMed PMID: 17917503. 13: Xia HJ, Dai DZ, Dai Y. Up-regulated inflammatory factors endothelin, NFkappaB, TNFalpha and iNOS involved in exaggerated cardiac arrhythmias in l-thyroxine-induced cardiomyopathy are suppressed by darusentan in rats. Life Sci. 2006 Oct 4;79(19):1812-9. Epub 2006 Jun 12. PubMed PMID: 16822527. 14: Traupe T, Ortmann J, Haas E, Münter K, Parekh N, Hofmann-Lehmann R, Baumann K, Barton M. Endothelin ETA receptor blockade with darusentan increases sodium and potassium excretion in aging rats. J Cardiovasc Pharmacol. 2006 Mar;47(3):456-62. PubMed PMID: 16633090. 15: Lip GY. Darusentan (Abbott Laboratories). IDrugs. 2001 Nov;4(11):1284-92. PubMed PMID: 15942834. 16: Anand I, McMurray J, Cohn JN, Konstam MA, Notter T, Quitzau K, Ruschitzka F, Lüscher TF; EARTH investigators. Long-term effects of darusentan on left-ventricular remodelling and clinical outcomes in the EndothelinA Receptor Antagonist Trial in Heart Failure (EARTH): randomised, double-blind, placebo-controlled trial. Lancet. 2004 Jul 24-30;364(9431):347-54. PubMed PMID: 15276394. 17: Bergler-Klein J, Pacher R, Berger R, Bojic A, Stanek B. Neurohumoral and hemodynamic effects of the selective endothelin antagonist darusentan in advanced chronic heart failure. J Heart Lung Transplant. 2004 Jan;23(1):20-7. PubMed PMID: 14734123. 18: Witte K, Reitenbach I, Stolpe K, Schilling L, Kirchengast M, Lemmer B. Effects of the endothelin a receptor antagonist darusentan on blood pressure and vascular contractility in type 2 diabetic Goto-Kakizaki rats. J Cardiovasc Pharmacol. 2003 Jun;41(6):890-6. PubMed PMID: 12775966. 19: Rothermund L, Traupe T, Dieterich M, Kossmehl P, Yagil C, Yagil Y, Kreutz R. Nephroprotective effects of the endothelin ET(A) receptor antagonist darusentan in salt-sensitive genetic hypertension. Eur J Pharmacol. 2003 May 16;468(3):209-16. PubMed PMID: 12754059. 20: Philipp S, Monti J, Pagel I, Langenickel T, Notter T, Ruschitzka F, Lüscher T, Dietz R, Willenbrock R. Treatment with darusentan over 21 days improved cGMP generation in patients with chronic heart failure. Clin Sci (Lond). 2002 Aug;103 Suppl 48:249S-253S. PubMed PMID: 12193097.