Sacubitrilat | LBQ-657 | CAS#149709-44-4 | endopeptidase inhibitor

MedKoo Cat#: 206449 | Name: Sacubitrilat

Description:

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

Sacubitrilat, also known as LBQ657, is endopeptidase inhibitor. Sacubitrilat 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.

Chemical Structure

Sacubitrilat

CAS#149709-44-4

Theoretical Analysis

MedKoo Cat#: 206449

Name: Sacubitrilat

CAS#: 149709-44-4

Chemical Formula: C22H25NO5

Exact Mass: 383.1733

Molecular Weight: 383.44

Elemental Analysis: C, 68.91; H, 6.57; N, 3.65; O, 20.86

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 400.00	Ready to ship
100mg	USD 650.00	Ready to ship
250mg	USD 1,350.00	Ready to ship
500mg	USD 2,350.00	Ready to ship

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Related CAS #

No Data

Synonym

LBQ-657; LBQ 657; LBQ657; Sacubitrilat

IUPAC/Chemical Name

(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-(3-carboxypropanamido)-2-methylpentanoic acid

InChi Key

DOBNVUFHFMVMDB-BEFAXECRSA-N

InChi Code

InChI=1S/C22H25NO5/c1-15(22(27)28)13-19(23-20(24)11-12-21(25)26)14-16-7-9-18(10-8-16)17-5-3-2-4-6-17/h2-10,15,19H,11-14H2,1H3,(H,23,24)(H,25,26)(H,27,28)/t15-,19+/m1/s1

SMILES Code

O=C(O)[C@H](C)C[C@H](NC(CCC(O)=O)=O)CC1=CC=C(C2=CC=CC=C2)C=C1

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# A22T02K15

QC Data

View QC data: current batch, Lot# A22T02K15

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Sacubitrilat (Desethyl Sacubitril) is an active neprilysin (NEP) inhibitor.

In vitro activity:

N/A

In vivo activity:

This study demonstrates that neprilysin inhibitor Sac directly improves Ca2+ homeostasis in human end‐stage HF by reducing pro‐arrhythmogenic SR Ca2+ leak without acutely affecting systolic Ca2+ release and inotropy. Reference: ESC Heart Fail. 2020 Oct;7(5):2992-3002. https://pubmed.ncbi.nlm.nih.gov/32710603/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	78.24
	DMSO	77.0	200.81
	Ethanol	77.0	200.81

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 383.44 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:

1. Eiringhaus J, Wünsche CM, Tirilomis P, Herting J, Bork N, Nikolaev VO, Hasenfuss G, Sossalla S, Fischer TH. Sacubitrilat reduces pro-arrhythmogenic sarcoplasmic reticulum Ca2+ leak in human ventricular cardiomyocytes of patients with end-stage heart failure. ESC Heart Fail. 2020 Oct;7(5):2992-3002. doi: 10.1002/ehf2.12918. Epub 2020 Jul 25. PMID: 32710603; PMCID: PMC7586991.

In vitro protocol:

N/A

In vivo protocol:

1: Eiringhaus J, Wünsche CM, Tirilomis P, Herting J, Bork N, Nikolaev VO, Hasenfuss G, Sossalla S, Fischer TH. Sacubitrilat reduces pro-arrhythmogenic sarcoplasmic reticulum Ca2+ leak in human ventricular cardiomyocytes of patients with end-stage heart failure. ESC Heart Fail. 2020 Oct;7(5):2992-3002. doi: 10.1002/ehf2.12918. Epub 2020 Jul 25. PMID: 32710603; PMCID: PMC7586991. 2: Kumbhar N, Nimal S, Patil D, Kaiser VF, Haupt J, Gacche RN. Repurposing of neprilysin inhibitor 'sacubitrilat' as an anti-cancer drug by modulating epigenetic and apoptotic regulators. Sci Rep. 2023 Jun 19;13(1):9952. doi: 10.1038/s41598-023-36872-0. PMID: 37336927; PMCID: PMC10279647. 3: Ayalasomayajula S, Langenickel T, Pal P, Boggarapu S, Sunkara G. Clinical Pharmacokinetics of Sacubitril/Valsartan (LCZ696): A Novel Angiotensin Receptor- Neprilysin Inhibitor. Clin Pharmacokinet. 2017 Dec;56(12):1461-1478. doi: 10.1007/s40262-017-0543-3. Erratum in: Clin Pharmacokinet. 2018 Jan;57(1):105-123. doi: 10.1007/s40262-017-0558-9. PMID: 28417439. 4: Giri P, Joshi V, Giri S, Delvadia P, Jain MR. Simultaneous determination of sacubitrilat and fimasartan in rat plasma by a triple quad liquid chromatography-tandem mass spectrometry method utilizing electrospray ionization in positive mode. Biomed Chromatogr. 2021 Feb;35(2):e4981. doi: 10.1002/bmc.4981. Epub 2020 Sep 18. PMID: 32895916. 5: Primessnig U, Deißler PM, Wakula P, Tran KL, Hohendanner F, von Lewinski D, Blaschke F, Knosalla C, Falk V, Pieske B, Grubitzsch H, Heinzel FR. Effects of BNP and Sacubitrilat/Valsartan on Atrial Functional Reserve and Arrhythmogenesis in Human Myocardium. Front Cardiovasc Med. 2022 Jul 5;9:859014. doi: 10.3389/fcvm.2022.859014. PMID: 35865376; PMCID: PMC9294287. 6: He Y, Jin Y, Xue H, Liu R, Zhang M, Liao R, Chen M, Zhou X, He X, Qin M, Li K, Zou H, Gan Y, Wang Z, Zheng L, Zhong H, Fu P. Pharmacokinetics and pharmacodynamics of sacubitril/valsartan in peritoneal dialysis patients. Nephrol Dial Transplant. 2023 Jul 31;38(8):1880-1889. doi: 10.1093/ndt/gfad038. PMID: 36787894. 7: Li Q, Fang Y, Peng DW, Li LA, Deng CY, Yang H, Kuang SJ, Li QQ, Zhang MZ, Zeng P, Zhang QH, Liu Y, Deng H, Wei W, Xue YM, Wu SL, Rao F. Sacubitril/valsartan reduces susceptibility to atrial fibrillation by improving atrial remodeling in spontaneously hypertensive rats. Eur J Pharmacol. 2023 Aug 5;952:175754. doi: 10.1016/j.ejphar.2023.175754. Epub 2023 May 12. PMID: 37182595. 8: Ayalasomayajula S, Langenickel T, Pal P, Boggarapu S, Sunkara G. Erratum to: Clinical Pharmacokinetics of Sacubitril/Valsartan (LCZ696): A Novel Angiotensin Receptor-Neprilysin Inhibitor. Clin Pharmacokinet. 2018 Jan;57(1):105-123. doi: 10.1007/s40262-017-0558-9. Erratum for: Clin Pharmacokinet. 2017 Dec;56(12):1461-1478. doi: 10.1007/s40262-017-0543-3. PMID: 28527109. 9: Uijl E, Roksnoer LC, Hoorn EJ, Danser AH. From ARB to ARNI in Cardiovascular Control. Curr Hypertens Rep. 2016 Dec;18(12):86. doi: 10.1007/s11906-016-0694-x. PMID: 27837397; PMCID: PMC5106495. 10: Kulmatycki KM, Langenickel T, Ng WH, Pal P, Zhou W, Lin TH, Rajman I, Chandra P, Sunkara G. Pharmacokinetics and safety of sacubitril/valsartan (LCZ696) in patients with mild and moderate hepatic impairment . Int J Clin Pharmacol Ther. 2017 Sep;55(9):728-739. doi: 10.5414/CP202988. PMID: 28737127. 11: Yang Q, Cao P, Lv Y, Peng H, Zhai X. Development and validation of a sensitive and simple LC-MS/MS method for simultaneous quantitation of valsartan, sacubitril and sacubitrilat in pediatric population. J Pharm Biomed Anal. 2024 Jan 20;238:115829. doi: 10.1016/j.jpba.2023.115829. Epub 2023 Oct 30. PMID: 37948774. 12: Litwin SE, East CA. Assessing clinical and biomarker characteristics to optimize the benefits of sacubitril/valsartan in heart failure. Front Cardiovasc Med. 2022 Dec 22;9:1058998. doi: 10.3389/fcvm.2022.1058998. PMID: 36620638; PMCID: PMC9815716. 13: Lai W, Huang R, Wang B, Shi M, Guo F, Li L, Ren Q, Tao S, Fu P, Ma L. Novel aspect of neprilysin in kidney fibrosis via ACSL4-mediated ferroptosis of tubular epithelial cells. MedComm (2020). 2023 Jul 14;4(4):e330. doi: 10.1002/mco2.330. PMID: 37457659; PMCID: PMC10349188. 14: Avataneo V, Fanelli E, De Nicolò A, Rabbia F, Palermiti A, Pappaccogli M, Cusato J, De Rosa FG, D'Avolio A, Veglio F. A Non-Invasive Method for Detection of Antihypertensive Drugs in Biological Fluids: The Salivary Therapeutic Drug Monitoring. Front Pharmacol. 2022 Jan 5;12:755184. doi: 10.3389/fphar.2021.755184. PMID: 35069191; PMCID: PMC8766966. 15: Ayalasomayajula SP, Langenickel TH, Jordaan P, Zhou W, Chandra P, Albrecht D, Pal P, Rajman I, Sunkara G. Effect of renal function on the pharmacokinetics of LCZ696 (sacubitril/valsartan), an angiotensin receptor neprilysin inhibitor. Eur J Clin Pharmacol. 2016 Sep;72(9):1065-73. doi: 10.1007/s00228-016-2072-7. Epub 2016 May 26. PMID: 27230850. 16: Akahori M, Ayalasomayajula S, Langenickel T, Pal P, Zhou W, Sunkara G. Pharmacokinetics After Single Ascending Dose, Food Effect, and Safety of Sacubitril/Valsartan (LCZ696), an Angiotensin Receptor and Neprilysin Inhibitor, in Healthy Japanese Subjects. Eur J Drug Metab Pharmacokinet. 2017 Jun;42(3):407-416. doi: 10.1007/s13318-016-0354-1. PMID: 27324506. 17: Bibika M, Kanellopoulos P, Rouchota M, Loudos G, Nock BA, Krenning EP, Maina T. Diagnosis of Prostate Cancer with a Neurotensin-Bombesin Radioligand Combination-First Preclinical Results. Pharmaceutics. 2024 Sep 19;16(9):1223. doi: 10.3390/pharmaceutics16091223. PMID: 39339259; PMCID: PMC11435135. 18: Sankhe R, Rathi E, Manandhar S, Kumar A, Pai SRK, Kini SG, Kishore A. Repurposing of existing FDA approved drugs for Neprilysin inhibition: An in- silico study. J Mol Struct. 2021 Jan 15;1224:129073. doi: 10.1016/j.molstruc.2020.129073. Epub 2020 Aug 12. PMID: 32834116; PMCID: PMC7422802. 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. doi: 10.5414/CP202604. PMID: 27719743. 20: Schoenfeld HA, West T, Verghese PB, Holubasch M, Shenoy N, Kagan D, Buono C, Zhou W, DeCristofaro M, Douville J, Goodrich GG, Mansfield K, Saravanan C, Cumin F, Webb RL, Bateman RJ. The effect of angiotensin receptor neprilysin inhibitor, sacubitril/valsartan, on central nervous system amyloid-β concentrations and clearance in the cynomolgus monkey. Toxicol Appl Pharmacol. 2017 May 15;323:53-65. doi: 10.1016/j.taap.2017.03.014. Epub 2017 Mar 15. PMID: 28315356.