Sacubitril sodium
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MedKoo CAT#: 329600

CAS#: 149690-05-1 (sodium)

Description: Sacubitril, also known as AHU377, is angiotensin receptor neprilysin inhibitor being studied for use in combination with valsartan for heart failure. Sacubitril is a prodrug that is activated to LBQ657 by de-ethylation via esterases. LBQ657 inhibits the enzyme neprilysin, which is responsible for the degradation of atrial and brain natriuretic peptide, two blood pressure lowering peptides that work mainly by reducing blood volume.


Price and Availability

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Price

200mg
USD 150
2g
USD 850
25g
USD 3650
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500mg
USD 250
5g
USD 1650
50g
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Size
Price

1g
USD 450
10g
USD 2850
100g
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Sacubitril sodium purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 20g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329600
Name: Sacubitril sodium
CAS#: 149690-05-1 (sodium)
Chemical Formula: C24H28NNaO5
Exact Mass:
Molecular Weight: 433.4798
Elemental Analysis: C, 66.50; H, 6.51; N, 3.23; Na, 5.30; O, 18.45


Related CAS #: 1369773-39-6 (hemi-calcium)   149709-62-6 (free acid)   149690-05-1 (sodium)   936623-90-4 (mixture with valsartan)  

Synonym: Sacubitril sodium; AHU377; AHU 377; AHU-377; LCZ696.

IUPAC/Chemical Name: sodium 4-(((2S,4R)-1-([1,1'-biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoate

InChi Key: RRTBVEJIZWGATF-JKSHRDEXSA-M

InChi Code: InChI=1S/C24H29NO5.Na/c1-3-30-24(29)17(2)15-21(25-22(26)13-14-23(27)28)16-18-9-11-20(12-10-18)19-7-5-4-6-8-19;/h4-12,17,21H,3,13-16H2,1-2H3,(H,25,26)(H,27,28);/q;+1/p-1/t17-,21+;/m1./s1

SMILES Code: O=C([O-])CCC(N[C@@H](C[C@@H](C)C(OCC)=O)CC1=CC=C(C2=CC=CC=C2)C=C1)=O.[Na+]


Technical Data

Appearance:
Brown solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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: Fox H, Bitter T, Horstkotte D, Oldenburg O. Resolution of Cheyne-Stokes Respiration after Treatment of Heart Failure with Sacubitril/Valsartan: A First Case Report. Cardiology. 2017 Feb 9;137(2):96-99. doi: 10.1159/000455118. [Epub ahead of print] PubMed PMID: 28178694.

2: Böhm M, Young R, Jhund PS, Solomon SD, Gong J, Lefkowitz MP, Rizkala AR, Rouleau JL, Shi VC, Swedberg K, Zile MR, Packer M, McMurray JJ. Systolic blood pressure, cardiovascular outcomes and efficacy and safety of sacubitril/valsartan (LCZ696) in patients with chronic heart failure and reduced ejection fraction: results from PARADIGM-HF. Eur Heart J. 2017 Feb 1. doi: 10.1093/eurheartj/ehw570. [Epub ahead of print] PubMed PMID: 28158398.

3: Kaplinsky E. Changing the treatment of heart failure with reduced ejection fraction: clinical use of sacubitril-valsartan combination. J Geriatr Cardiol. 2016 Nov;13(11):914-923. doi: 10.11909/j.issn.1671-5411.2016.11.006. Review. PubMed PMID: 28133468; PubMed Central PMCID: PMC5253408.

4: Williams B, Cockcroft JR, Kario K, Zappe DH, Brunel PC, Wang Q, Guo W. Effects of Sacubitril/Valsartan Versus Olmesartan on Central Hemodynamics in the Elderly With Systolic Hypertension: The PARAMETER Study. Hypertension. 2017 Mar;69(3):411-420. doi: 10.1161/HYPERTENSIONAHA.116.08556. PubMed PMID: 28093466.

5: Lin W, Ji T, Einolf H, Ayalasomayajula S, Lin TH, Hanna I, Heimbach T, Breen C, Jarugula V, He H. Evaluation of Drug-Drug Interaction Potential Between Sacubitril/Valsartan (LCZ696) and Statins Using a Physiologically Based Pharmacokinetic Model. J Pharm Sci. 2017 Jan 13. pii: S0022-3549(17)30010-2. doi: 10.1016/j.xphs.2017.01.007. [Epub ahead of print] PubMed PMID: 28089685.

6: Tyler JM, Teerlink JR. The safety of sacubitril-valsartan for the treatment of chronic heart failure. Expert Opin Drug Saf. 2017 Feb;16(2):257-263. doi: 10.1080/14740338.2017.1279144. PubMed PMID: 28060547.

7: Wang JG, Yukisada K, Sibulo A Jr, Hafeez K, Jia Y, Zhang J. Efficacy and safety of sacubitril/valsartan (LCZ696) add-on to amlodipine in Asian patients with systolic hypertension uncontrolled with amlodipine monotherapy. J Hypertens. 2016 Dec 24. doi: 10.1097/HJH.0000000000001219. [Epub ahead of print] PubMed PMID: 28030431.

8: Tsutsui H, Momomura S, Saito Y, Ito H, Yamamoto K, Ohishi T, Okino N, Guo W. Efficacy and safety of sacubitril/valsartan (LCZ696) in Japanese patients with chronic heart failure and reduced ejection fraction: Rationale for and design of the randomized, double-blind PARALLEL-HF study. J Cardiol. 2016 Dec 23. pii: S0914-5087(16)30309-4. doi: 10.1016/j.jjcc.2016.11.011. [Epub ahead of print] PubMed PMID: 28024961.

9: Khder Y, Shi V, McMurray JJ, Lefkowitz MP. Sacubitril/Valsartan (LCZ696) in Heart Failure. Handb Exp Pharmacol. 2016 Dec 22. doi: 10.1007/164_2016_77. [Epub ahead of print] PubMed PMID: 28004291.

10: Sacubitril/valsartan for chronic heart failure. Aust Prescr. 2016 Dec;39(6):226-227. Review. PubMed PMID: 27990055; PubMed Central PMCID: PMC5155054.

11: Cheng J. Sacubitril/Valsartan (Entresto) for Heart Failure. Am Fam Physician. 2016 Oct 15;94(8):611-612. PubMed PMID: 27929235.

12: Supasyndh O, Sun N, Kario K, Hafeez K, Zhang J. Long-term (52-week) safety and efficacy of Sacubitril/valsartan in Asian patients with hypertension. Hypertens Res. 2016 Nov 17. doi: 10.1038/hr.2016.151. [Epub ahead of print] PubMed PMID: 27853163.

13: Wang TD, Tan RS, Lee HY, Ihm SH, Rhee MY, Tomlinson B, Pal P, Yang F, Hirschhorn E, Prescott MF, Hinder M, Langenickel TH. Effects of Sacubitril/Valsartan (LCZ696) on Natriuresis, Diuresis, Blood Pressures, and NT-proBNP in Salt-Sensitive Hypertension. Hypertension. 2017 Jan;69(1):32-41. PubMed PMID: 27849566.

14: Ezekowitz JA. Hyperkalemia, Sacubitril/Valsartan, and Mineralocorticoid Antagonists in Patients With Heart Failure. JAMA Cardiol. 2017 Jan 1;2(1):86-87. doi: 10.1001/jamacardio.2016.4731. PubMed PMID: 27842180.

15: Desai AS, Vardeny O, Claggett B, McMurray JJ, Packer M, Swedberg K, Rouleau JL, Zile MR, Lefkowitz M, Shi V, Solomon SD. Reduced Risk of Hyperkalemia During Treatment of Heart Failure With Mineralocorticoid Receptor Antagonists by Use of Sacubitril/Valsartan Compared With Enalapril: A Secondary Analysis of the PARADIGM-HF Trial. JAMA Cardiol. 2017 Jan 1;2(1):79-85. doi: 10.1001/jamacardio.2016.4733. PubMed PMID: 27842179.

16: Brandenburg VM, Rocca HB, Marx N. [Sacubitril / Valsartan in patients with diabetes and heart failure]. Dtsch Med Wochenschr. 2016 Oct;141(22):1647-1649. German. PubMed PMID: 27824422.

17: Faber ES, Gavini M, Ramirez R, Sadovsky R. Rhabdomyolysis After Coadministration of Atorvastatin and Sacubitril/Valsartan (Entresto™) in a 63-Year-Old Woman. Drug Saf Case Rep. 2016 Dec;3(1):14. PubMed PMID: 27804100; PubMed Central PMCID: PMC5089965.

18: Kaplinsky E. Sacubitril/valsartan in heart failure: latest evidence and place in therapy. Ther Adv Chronic Dis. 2016 Nov;7(6):278-290. Review. PubMed PMID: 27803793; PubMed Central PMCID: PMC5076745.

19: Ayalasomayajula S, Langenickel TH, Chandra P, Wolfson ED, Albrecht D, Zhou W, Pal P, Rajman I, Sunkara G. Effect of food on the oral bioavailability of the angiotensin receptor - neprilysin inhibitor sacubitril/valsartan (LCZ696) in healthy subjects
. Int J Clin Pharmacol Ther. 2016 Dec;54(12):1012-1018. PubMed PMID: 27719743.

20: Fala L. Entresto (Sacubitril/Valsartan): First-in-Class Angiotensin Receptor Neprilysin Inhibitor FDA Approved for Heart Failure. Am Health Drug Benefits. 2016 Mar;9(Spec Feature):78-82. PubMed PMID: 27668049; PubMed Central PMCID: PMC5013841.