L 158809

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

MedKoo CAT#: 596395

CAS#: 133240-46-7

Description: L 158809 is an angiotensin II type 1 receptor antagonist.


Price and Availability

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L 158809 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 596395
Name: L 158809
CAS#: 133240-46-7
Chemical Formula: C24H23N7
Exact Mass: 409.2015
Molecular Weight: 409.49
Elemental Analysis: C, 70.39; H, 5.66; N, 23.94


Synonym: L 158809; L-158809; L158809; L-158,809;

IUPAC/Chemical Name: 3-((2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine

InChi Key: YFWXFHNZGKNDBC-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H23N7/c1-4-21-26-22-15(2)13-16(3)25-24(22)31(21)14-17-9-11-18(12-10-17)19-7-5-6-8-20(19)23-27-29-30-28-23/h5-13H,4,14H2,1-3H3,(H,27,28,29,30)

SMILES Code: CC1=C2C(N(CC3=CC=C(C4=CC=CC=C4C5=NNN=N5)C=C3)C(CC)=N2)=NC(C)=C1


Technical Data

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

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).

Harmonized System Code:
293490


References

1: Saez F, Reverte V, Paliege A, Moreno JM, Llinás MT, Bachmann S, Salazar FJ. Sex-dependent hypertension and renal changes in aged rats with altered renal development. Am J Physiol Renal Physiol. 2014 Aug 15;307(4):F461-70. doi: 10.1152/ajprenal.00198.2014. Epub 2014 Jun 18. PubMed PMID: 24944267.

2: Kitada K, Yui N, Mori T, Ohkita M, Matsumura Y. Vasoprotective effects of an endothelin receptor antagonist in ovariectomized female rats. Life Sci. 2014 Nov 24;118(2):379-85. doi: 10.1016/j.lfs.2014.01.009. Epub 2014 Jan 24. PubMed PMID: 24468711.

3: Moore ED, Kooshki M, Wheeler KT, Metheny-Barlow LJ, Robbins ME. Differential expression of Homer1a in the hippocampus and cortex likely plays a role in radiation-induced brain injury. Radiat Res. 2014 Jan;181(1):21-32. doi: 10.1667/RR13475.1. Epub 2013 Dec 30. PubMed PMID: 24377717; PubMed Central PMCID: PMC4118588.

4: Meinen S, Lin S, Ruegg MA. Angiotensin II type 1 receptor antagonists alleviate muscle pathology in the mouse model for laminin-α2-deficient congenital muscular dystrophy (MDC1A). Skelet Muscle. 2012 Sep 3;2(1):18. doi: 10.1186/2044-5040-2-18. PubMed PMID: 22943509; PubMed Central PMCID: PMC3598380.

5: Camelo JS Jr, Martins AR, Rosa E, Ramos SG, Hehre D, Bancalari E, Suguihara C. Angiotensin II type 1 receptor blockade partially attenuates hypoxia-induced pulmonary hypertension in newborn piglets: relationship with the nitrergic system. Braz J Med Biol Res. 2012 Feb;45(2):163-71. Epub 2012 Feb 9. PubMed PMID: 22310488; PubMed Central PMCID: PMC3854258.

6: Gilliam-Davis S, Gallagher PE, Payne VS, Kasper SO, Tommasi EN, Westwood BM, Robbins ME, Chappell MC, Diz DI. Long-term systemic angiotensin II type 1 receptor blockade regulates mRNA expression of dorsomedial medulla renin-angiotensin system components. Physiol Genomics. 2011 Jul 14;43(13):829-35. doi: 10.1152/physiolgenomics.00167.2010. Epub 2011 May 3. PubMed PMID: 21540301; PubMed Central PMCID: PMC3132839.

7: Chitravanshi VC, Sapru HN. Cardiovascular responses elicited by a new endogenous angiotensin in the nucleus tractus solitarius of the rat. Am J Physiol Heart Circ Physiol. 2011 Jan;300(1):H230-40. doi: 10.1152/ajpheart.00861.2010. Epub 2010 Nov 12. PubMed PMID: 21076017; PubMed Central PMCID: PMC3023243.

8: Conner KR, Payne VS, Forbes ME, Robbins ME, Riddle DR. Effects of the AT1 receptor antagonist L-158,809 on microglia and neurogenesis after fractionated whole-brain irradiation. Radiat Res. 2010 Jan;173(1):49-61. doi: 10.1667/RR1821.1. PubMed PMID: 20041759; PubMed Central PMCID: PMC2811039.

9: Oruc N, Ozutemiz O, Nart D, Yuce G, Celik HA, Ilter T. Inhibition of renin-angiotensin system in experimental acute pancreatitis in rats: a new therapeutic target? Exp Toxicol Pathol. 2010 Jul;62(4):353-60. doi: 10.1016/j.etp.2009.05.001. Epub 2009 Jun 13. PubMed PMID: 19525099.

10: Kvochina L, Hasser EM, Heesch CM. Pregnancy decreases GABAergic inhibition of the hypothalamic paraventricular nucleus. Physiol Behav. 2009 May 25;97(2):171-9. doi: 10.1016/j.physbeh.2009.02.018. Epub 2009 Feb 28. PubMed PMID: 19254733; PubMed Central PMCID: PMC3906727.

11: Tran LT, MacLeod KM, McNeill JH. Endothelin-1 modulates angiotensin II in the development of hypertension in fructose-fed rats. Mol Cell Biochem. 2009 May;325(1-2):89-97. doi: 10.1007/s11010-008-0023-z. Epub 2009 Jan 13. PubMed PMID: 19139972.

12: Robbins ME, Payne V, Tommasi E, Diz DI, Hsu FC, Brown WR, Wheeler KT, Olson J, Zhao W. The AT1 receptor antagonist, L-158,809, prevents or ameliorates fractionated whole-brain irradiation-induced cognitive impairment. Int J Radiat Oncol Biol Phys. 2009 Feb 1;73(2):499-505. doi: 10.1016/j.ijrobp.2008.09.058. Epub 2008 Dec 10. PubMed PMID: 19084353; PubMed Central PMCID: PMC2631653.

13: Iwata K, Sohda T, Irie M, Takeyama Y, Anan A, Shakado S, Sakisaka S. Angiotensin II type 1 receptor antagonist improves the prognosis in rats displaying liver cirrhosis induced by a choline-deficient diet. J Gastrointestin Liver Dis. 2008 Mar;17(1):21-5. PubMed PMID: 18392239.

14: Lund DD, Brooks RM, Faraci FM, Heistad DD. Role of angiotensin II in endothelial dysfunction induced by lipopolysaccharide in mice. Am J Physiol Heart Circ Physiol. 2007 Dec;293(6):H3726-31. Epub 2007 Oct 26. PubMed PMID: 17965276.

15: Bian YL, Qi YX, Yan ZQ, Long DK, Shen BR, Jiang ZL. A proteomic analysis of aorta from spontaneously hypertensive rat: RhoGDI alpha upregulation by angiotensin II via AT(1) receptor. Eur J Cell Biol. 2008 Feb;87(2):101-10. Epub 2007 Oct 25. PubMed PMID: 17963997.

16: Cohen EP, Fish BL, Sharma M, Li XA, Moulder JE. Role of the angiotensin II type-2 receptor in radiation nephropathy. Transl Res. 2007 Aug;150(2):106-15. Epub 2007 May 25. PubMed PMID: 17656330; PubMed Central PMCID: PMC2034340.

17: Gilliam-Davis S, Payne VS, Kasper SO, Tommasi EN, Robbins ME, Diz DI. Long-term AT1 receptor blockade improves metabolic function and provides renoprotection in Fischer-344 rats. Am J Physiol Heart Circ Physiol. 2007 Sep;293(3):H1327-33. Epub 2007 Jul 6. PubMed PMID: 17616746.

18: Saez F, Castells MT, Zuasti A, Salazar F, Reverte V, Loria A, Salazar FJ. Sex differences in the renal changes elicited by angiotensin II blockade during the nephrogenic period. Hypertension. 2007 Jun;49(6):1429-35. Epub 2007 Apr 2. PubMed PMID: 17404180.

19: Kramer A, van den Hoven M, Rops A, Wijnhoven T, van den Heuvel L, Lensen J, van Kuppevelt T, van Goor H, van der Vlag J, Navis G, Berden JH. Induction of glomerular heparanase expression in rats with adriamycin nephropathy is regulated by reactive oxygen species and the renin-angiotensin system. J Am Soc Nephrol. 2006 Sep;17(9):2513-20. Epub 2006 Aug 9. PubMed PMID: 16899518.

20: Li YL, Schultz HD. Enhanced sensitivity of Kv channels to hypoxia in the rabbit carotid body in heart failure: role of angiotensin II. J Physiol. 2006 Aug 15;575(Pt 1):215-27. Epub 2006 Jun 15. PubMed PMID: 16777942; PubMed Central PMCID: PMC1819433.