Lisinopril hydrate | CAS#83915-83-7 | 76547-98-3 | ACE inhibitor

MedKoo Cat#: 540271 | Name: Lisinopril hydrate

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Description:

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

Lisinopril is an enalapril analog and ACE inhibitor used to treat hypertension, congestive heart failure, myocardial infarction, and retinal disorders. It also inhibits left ventricular dilation, suppresses myocardial hypertrophy, and prevents the development of paraquat-induced lung fibrosis.

Chemical Structure

Lisinopril hydrate

CAS#83915-83-7 (hydrate)

Theoretical Analysis

MedKoo Cat#: 540271

Name: Lisinopril hydrate

CAS#: 83915-83-7 (hydrate)

Chemical Formula: C21H35N3O7

Exact Mass:

Molecular Weight: 441.53

Elemental Analysis: C, 57.13; H, 7.99; N, 9.52; O, 25.37

Price and Availability

Size	Price	Availability	Quantity
1g	USD 350.00	2 Weeks
5g	USD 750.00	2 Weeks

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Related CAS #

76547-98-3 (free) 83915-83-7 (hydrate)

Synonym

Lisinopril; Lisinopril dihydrate; MK-521; MK521; MK 521; Prinivil; Qbrelis; Ranolip; Renacor

IUPAC/Chemical Name

((S)-1-carboxy-3-phenylpropyl)-L-lysyl-L-proline dihydrate

InChi Key

CZRQXSDBMCMPNJ-ZUIPZQNBSA-N

InChi Code

InChI=1S/C21H31N3O5.2H2O/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15;;/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29);2*1H2/t16-,17-,18-;;/m0../s1

SMILES Code

O=C(O)[C@H]1N(C([C@H](CCCCN)N[C@H](C(O)=O)CCC2=CC=CC=C2)=O)CCC1.[H]O[H].[H]O[H]

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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lisinopril dihydrate (MK-521 dihydrate) is angiotensin-converting enzyme inhibitor.

In vitro activity:

Additionally, in vitro experiments with hPBMCs showed that DPP4 inhibitors upregulated mRNA expression of MMP9 and ACE2, which are responsible for the pathophysiology of BP in monocytes/macrophages. Furthermore, lisinopril and Mas receptor (MasR) inhibitors suppressed DPP4 inhibitor-induced upregulation of MMP9. Reference: Front Immunol. 2023 Jan 5;13:1084960. https://pubmed.ncbi.nlm.nih.gov/36685490/

In vivo activity:

In this study, 2 groups from each of the 3 rat strains had their hearts irradiated (8 Gy X 5 fractions). Lisinopril mitigated the increase in posterior wall thickness. Radiation did not alter mitochondrial respiration in PBMC from BN or SSBN6. However, maximal mitochondrial respiration and spare capacity were reduced by radiation in PBMC from SS rats (p=0.016 and 0.002 respectively, 9-10 rats/group) and this effect was mitigated by lisinopril (p=0.04 and 0.023 respectively, 9-10 rats/group). Reference: Front Oncol. 2022 Mar 2;12:828177. https://pubmed.ncbi.nlm.nih.gov/35311118/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.0	2.26
	Water	26.7	60.39

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 441.53 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. Nozawa K, Suzuki T, Kayanuma G, Yamamoto H, Nagayasu K, Shirakawa H, Kaneko S. Lisinopril prevents bullous pemphigoid induced by dipeptidyl peptidase 4 inhibitors via the Mas receptor pathway. Front Immunol. 2023 Jan 5;13:1084960. doi: 10.3389/fimmu.2022.1084960. PMID: 36685490; PMCID: PMC9849361. 2. Becker Y, Stock C. The ACE Inhibitor Lisinopril Stimulates Melanoma Cell Invasiveness by Inducing MMP2 Secretion. Cell Physiol Biochem. 2022 Sep 5;56(5):457-483. doi: 10.33594/000000570. PMID: 36057984. 3. Ortiz de Choudens S, Sparapani R, Narayanan J, Lohr N, Gao F, Fish BL, Zielonka M, Gasperetti T, Veley D, Beyer A, Olson J, Jacobs ER, Medhora M. Lisinopril Mitigates Radiation-Induced Mitochondrial Defects in Rat Heart and Blood Cells. Front Oncol. 2022 Mar 2;12:828177. doi: 10.3389/fonc.2022.828177. PMID: 35311118; PMCID: PMC8924663. 4. Brown AK, Nichols A, Coley CA, Ekperikpe US, McPherson KC, Shields CA, Poudel B, Cornelius DC, Williams JM. Treatment With Lisinopril Prevents the Early Progression of Glomerular Injury in Obese Dahl Salt-Sensitive Rats Independent of Lowering Arterial Pressure. Front Physiol. 2021 Dec 17;12:765305. doi: 10.3389/fphys.2021.765305. PMID: 34975523; PMCID: PMC8719629.

In vitro protocol:

In vivo protocol:

1. Ortiz de Choudens S, Sparapani R, Narayanan J, Lohr N, Gao F, Fish BL, Zielonka M, Gasperetti T, Veley D, Beyer A, Olson J, Jacobs ER, Medhora M. Lisinopril Mitigates Radiation-Induced Mitochondrial Defects in Rat Heart and Blood Cells. Front Oncol. 2022 Mar 2;12:828177. doi: 10.3389/fonc.2022.828177. PMID: 35311118; PMCID: PMC8924663. 2. Brown AK, Nichols A, Coley CA, Ekperikpe US, McPherson KC, Shields CA, Poudel B, Cornelius DC, Williams JM. Treatment With Lisinopril Prevents the Early Progression of Glomerular Injury in Obese Dahl Salt-Sensitive Rats Independent of Lowering Arterial Pressure. Front Physiol. 2021 Dec 17;12:765305. doi: 10.3389/fphys.2021.765305. PMID: 34975523; PMCID: PMC8719629.

1: Agarwal R, Sinha AD, Pappas MK, Abraham TN, Tegegne GG. Hypertension in hemodialysis patients treated with atenolol or lisinopril: a randomized controlled trial. Nephrol Dial Transplant. 2014 Mar;29(3):672-81. doi: 10.1093/ndt/gft515. Epub 2014 Jan 6. PubMed PMID: 24398888; PubMed Central PMCID: PMC3938300. 2: Yamal JM, Oparil S, Davis BR, Alderman MH, Calhoun DA, Cushman WC, Fendley HF, Franklin SS, Habib GB, Pressel SL, Probstfield JL, Sastrasinh S; ALLHAT Collaborative Research Group. Stroke outcomes among participants randomized to chlorthalidone, amlodipine or lisinopril in ALLHAT. J Am Soc Hypertens. 2014 Nov;8(11):808-19. doi: 10.1016/j.jash.2014.08.003. Epub 2014 Aug 19. PubMed PMID: 25455006; PubMed Central PMCID: PMC4254528. 3: Georgianos PI, Agarwal R. Effect of lisinopril and atenolol on aortic stiffness in patients on hemodialysis. Clin J Am Soc Nephrol. 2015 Apr 7;10(4):639-45. doi: 10.2215/CJN.09981014. Epub 2015 Mar 17. PubMed PMID: 25784174; PubMed Central PMCID: PMC4386263. 4: Gore PN, Badar VA, Hardas MM, Bansode VJ. Comparative effect of telmisartan vs lisinopril on blood pressure in patients of metabolic syndrome. Endocr Metab Immune Disord Drug Targets. 2015;15(1):64-70. PubMed PMID: 25440999. 5: Nwachukwu DC, Aneke EI, Obika LF, Nwachukwu NZ. Effects of aqueous extract of Hibiscus sabdariffa on the renin-angiotensin-aldosterone system of Nigerians with mild to moderate essential hypertension: A comparative study with lisinopril. Indian J Pharmacol. 2015 Sep-Oct;47(5):540-5. doi: 10.4103/0253-7613.165194. PubMed PMID: 26600645; PubMed Central PMCID: PMC4621677. 6: Kuntze LB, Antonio RC, Izidoro-Toledo TC, Meschiari CA, Tanus-Santos JE, Gerlach RF. Captopril and lisinopril only inhibit matrix metalloproteinase-2 (MMP-2) activity at millimolar concentrations. Basic Clin Pharmacol Toxicol. 2014 Mar;114(3):233-9. PubMed PMID: 25767848. 7: de Diego M, Soto J, Mennickent S. Stability-indicating LC method for the simultaneous determination of lisinopril and hydrochlorothiazide. J Chromatogr Sci. 2014 Nov-Dec;52(10):1193-7. doi: 10.1093/chromsci/bmt176. Epub 2013 Dec 1. PubMed PMID: 24297524. 8: Trachtman H, Frymoyer A, Lewandowski A, Greenbaum LA, Feig DI, Gipson DS, Warady BA, Goebel JW, Schwartz GJ, Lewis K, Anand R, Patel UD; Best Pharmaceuticals for Children Act-Pediatric Trials Network Administrative Core Committee. Pharmacokinetics, Pharmacodynamics, and Safety of Lisinopril in Pediatric Kidney Transplant Patients: Implications for Starting Dose Selection. Clin Pharmacol Ther. 2015 Jul;98(1):25-33. doi: 10.1002/cpt.127. Epub 2015 May 2. PubMed PMID: 25807932; PubMed Central PMCID: PMC4536255. 9: Denti P, Sharp SK, Kröger WL, Schwager SL, Mahajan A, Njoroge M, Gibhard L, Smit I, Chibale K, Wiesner L, Sturrock ED, Davies NH. Pharmacokinetic evaluation of lisinopril-tryptophan, a novel C-domain ACE inhibitor. Eur J Pharm Sci. 2014 Jun 2;56:113-9. doi: 10.1016/j.ejps.2014.01.012. Epub 2014 Feb 20. PubMed PMID: 24561703. 10: Semwal R, Semwal RB, Semwal DK. A gastroretentive drug delivery system of lisinopril imbibed on isabgol-husk. Curr Drug Deliv. 2014;11(3):371-9. PubMed PMID: 24144200. 11: Lewis JC, Alsop JA. A 13-year review of lisinopril ingestions in children less than 6 years of age. Clin Toxicol (Phila). 2013 Nov;51(9):864-70. doi: 10.3109/15563650.2013.834533. Epub 2013 Aug 22. PubMed PMID: 23964854. 12: Mutolo D, Cinelli E, Bongianni F, Evangelista S, Pantaleo T. Comparison between the effects of lisinopril and losartan on the cougn reflex in anesthetized and awake rabbits. J Physiol Pharmacol. 2013 Apr;64(2):201-10. PubMed PMID: 23756395. 13: Danafar H, Rostamizadeh K, Davaran S, Hamidi M. PLA-PEG-PLA copolymer-based polymersomes as nanocarriers for delivery of hydrophilic and hydrophobic drugs: preparation and evaluation with atorvastatin and lisinopril. Drug Dev Ind Pharm. 2014 Oct;40(10):1411-20. doi: 10.3109/03639045.2013.828223. Epub 2013 Aug 14. PubMed PMID: 23944838. 14: Winnicki W, Prehslauer A, Kletzmayr J, Herkner H, Sunder-Plassmann G, Brunner M, Hörl WH, Sengoelge G. Lisinopril pharmacokinetics and erythropoietin requirement in haemodialysis patients. Eur J Clin Invest. 2012 Oct;42(10):1087-93. doi: 10.1111/j.1365-2362.2012.02699.x. Epub 2012 Jul 28. PubMed PMID: 22845880. 15: Weiss RJ, Stapff M, Lin Y. Placebo effect and efficacy of nebivolol in patients with hypertension not controlled with lisinopril or losartan: a phase IV, randomized, placebo-controlled trial. Am J Cardiovasc Drugs. 2013 Apr;13(2):129-40. doi: 10.1007/s40256-013-0010-y. PubMed PMID: 23519546. 16: Amador Ríos Z, Ghaly ES. The Effect of Formulation Excipients and Thermal Treatment on the Release Properties of Lisinopril Spheres and Tablets. Biomed Res Int. 2015;2015:423615. doi: 10.1155/2015/423615. Epub 2015 Jun 21. PubMed PMID: 26185757; PubMed Central PMCID: PMC4491407. 17: Galeeva ZM, Galiavich AS. [A fixed-dose lisinopril and amlodipine combination in conjunction with rosuvastatin in patients with hypertensive disease and coronary heart disease]. Ter Arkh. 2014;86(9):71-6. Russian. PubMed PMID: 25518509. 18: Ijaz H, Qureshi J, Danish Z, Zaman M, Abdel-Daim M, Hanif M, Waheed I, Mohammad IS. Formulation and in-vitro evaluation of floating bilayer tablet of lisinopril maleate and metoprolol tartrate. Pak J Pharm Sci. 2015 Nov;28(6):2019-25. PubMed PMID: 26639495. 19: Kosenko E, Tikhonova L, Suslikov A, Kaminsky Y. Impacts of lisinopril and lisinopril plus simvastatin on erythrocyte and plasma arginase, nitrite, and nitrate in hypertensive patients. J Clin Pharmacol. 2012 Jan;52(1):102-9. doi: 10.1177/0091270010388647. Epub 2011 Mar 15. PubMed PMID: 21406601. 20: Yousefpour A, Modarress H, Goharpey F, Amjad-Iranagh S. Interaction of PEGylated anti-hypertensive drugs, amlodipine, atenolol and lisinopril with lipid bilayer membrane: A molecular dynamics simulation study. Biochim Biophys Acta. 2015 Aug;1848(8):1687-98. doi: 10.1016/j.bbamem.2015.04.016. Epub 2015 May 8. PubMed PMID: 25960186.