Lisinopril
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MedKoo CAT#: 318156

CAS#: 76547-98-3 (free)

Description: Lisinopril is a drug of the angiotensin-converting enzyme (ACE) inhibitor class used primarily in treatment of high blood pressure, heart failure, and after heart attacks. It is also used for preventing kidney and eye complications in people with diabetes. Its indications, contraindications, and side effects are as those for all ACE inhibitors. A number of properties distinguish it from other ACE inhibitors: It is hydrophilic, has a long half-life and tissue penetration, and is not metabolized by the liver.

Chemical Structure

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Lisinopril
CAS# 76547-98-3 (free)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318156
Name: Lisinopril
CAS#: 76547-98-3 (free)
Chemical Formula: C21H31N3O5
Exact Mass: 405.23
Molecular Weight: 405.495
Elemental Analysis: C, 62.20; H, 7.71; N, 10.36; O, 19.73

Price and Availability

Size Price Availability Quantity
1g USD 150
2g USD 250
5g USD 550
10g USD 850 2 Weeks
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Related CAS #: 76547-98-3 (free)   83915-83-7 (hydrate)    

Synonym: Lisinopril; Prinivil; Zestril; Linopril; Lisipril; Lysinopril;Lisinopril Maleate (1:1); Lisinopril Sulfate (1:2); Lysinopril MK-521; Prinivil; Zestril;

IUPAC/Chemical Name: (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid

InChi Key: RLAWWYSOJDYHDC-BZSNNMDCSA-N

InChi Code: InChI=1S/C21H31N3O5/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)/t16-,17-,18-/m0/s1

SMILES Code: C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O

Appearance: Solid powder

Purity: >97% (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
Instruction:
View handling instruction
Biological target: Lisinopril (MK-521) 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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
PBS (pH 7.2) 1.0 2.47

Preparing Stock Solutions

The following data is based on the product molecular weight 405.50 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
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: 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.
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.

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1: Akintunde JK, Bolarin OE, Akintunde DG. Garlic capsule and selenium-vitamins
ACE combination therapy modulate key antioxidant proteins and cellular adenosine
triphosphate in lisinopril-induced lung damage in rats. Drug Metabol Personal
Ther. 2016 Mar 1;31(1):47-54. doi: 10.1515/dmpt-2015-0035. PubMed PMID: 26943616.


2: Jiang M, Huang CR, Wang Q, Zhu YY, Wang J, Chen J, Shi JH. Combined
spectroscopies and molecular docking approach to characterizing the binding
interaction between lisinopril and bovine serum albumin. Luminescence. 2016
Mar;31(2):468-77. doi: 10.1002/bio.2984. Epub 2015 Aug 24. PubMed PMID: 26300521.


3: Simonyi G, Ferenci T. [Ramipril plus amlodipine and lisinopril plus amlodipine
fixed dose combinations and patient's adherence]. Orv Hetil. 2016 Jan
3;157(1):30-4. doi: 10.1556/650.2016.30344. Hungarian. PubMed PMID: 26708684.


4: Cinelli E, Bongianni F, Pantaleo T, Mutolo D. The cough reflex is upregulated
by lisinopril microinjected into the caudal nucleus tractus solitarii of the
rabbit. Respir Physiol Neurobiol. 2015 Dec;219:9-17. doi:
10.1016/j.resp.2015.07.013. Epub 2015 Jul 30. PubMed PMID: 26234277.


5: Thakur KS, Prakash A, Bisht R, Bansal PK. Beneficial effect of candesartan and
lisinopril against haloperidol-induced tardive dyskinesia in rat. J Renin
Angiotensin Aldosterone Syst. 2015 Dec;16(4):917-29. doi:
10.1177/1470320313515038. Epub 2014 Jan 24. PubMed PMID: 24464858.


6: 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.


7: Vieriu M, Tântaru G, Apostu M, Panainte AD, Bibire N. A NEW SPECTROPHOTOMETRIC
METHOD FOR THE ASSAY OF LISINOPRIL. Rev Med Chir Soc Med Nat Iasi. 2015
Oct-Dec;119(4):1199-204. PubMed PMID: 26793870.


8: 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.


9: Brower GL, Levick SP, Janicki JS. Differential Effects of Prevention and
Reversal Treatment with Lisinopril on Left Ventricular Remodelling in a Rat Model
of Heart Failure. Heart Lung Circ. 2015 Sep;24(9):919-24. doi:
10.1016/j.hlc.2015.02.023. Epub 2015 Mar 13. PubMed PMID: 25837018; PubMed
Central PMCID: PMC4564313.


10: 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.


11: 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.


12: 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.


13: PLOS Currents. Correction: a randomized, double-blind trial of lisinopril and
losartan for the treatment of cardiomyopathy in duchenne muscular dystrophy. PLoS
Curr. 2015 Mar 6;7. pii: ecurrents.md.995441cf82fd58a29c6e4fdd5cd36b89. doi:
10.1371/currents.md.995441cf82fd58a29c6e4fdd5cd36b89. PubMed PMID: 25821645;
PubMed Central PMCID: PMC4358986.


14: Heise CW, Beutler D, Bosak A, Orme G, Loli A, Graeme K. Massive Atenolol,
Lisinopril, and Chlorthalidone Overdose Treated with Endoscopic Decontamination,
Hemodialysis, Impella Percutaneous Left Ventricular Assist Device, and ECMO. J
Med Toxicol. 2015 Mar;11(1):110-4. doi: 10.1007/s13181-014-0419-y. PubMed PMID:
25146229; PubMed Central PMCID: PMC4371031.


15: Albarwani S, Al-Siyabi S, Al-Husseini I, Al-Ismail A, Al-Lawati I, Al-Bahrani
I, Tanira MO. Lisinopril alters contribution of nitric oxide and K(Ca) channels
to vasodilatation in small mesenteric arteries of spontaneously hypertensive
rats. Physiol Res. 2015;64(1):39-49. Epub 2014 Sep 5. PubMed PMID: 25194131.


16: Panov AV, Alugishvili MZ, Abesadze IT, Lohovinina NL, Korzenewskaya KV,
Titenkov IV, Kuleshova EV, Dyplyakov DV, Hohlunov SM, Kryukov AV, Libis RA,
Isayeva EN, Basyrova IR, Safonova DV. [The Antihypertensive Effect of the Fixed
Combination of Lisinopril and Amlodipine in Patients With Coronary Heart Disease
After Coronary Artery Bypass Grafting]. Kardiologiia. 2015;55(6):27-33. Russian.
PubMed PMID: 26625516.


17: Deb D, Bairy KL, Nayak V, Rao M. Comparative Effect of Lisinopril and
Fosinopril in Mitigating Learning and Memory Deficit in Scopolamine-Induced
Amnesic Rats. Adv Pharmacol Sci. 2015;2015:521718. doi: 10.1155/2015/521718. Epub
2015 Aug 2. PubMed PMID: 26300914; PubMed Central PMCID: PMC4537708.


18: 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.


19: Wong MC, Tam WW, Wang HH, Zhang D, Cheung CS, Yan BP, Leeder SR, Griffiths
SM. The effectiveness of perindopril vs. lisinopril on reducing the incidence of
diabetes and renal diseases: A cohort study of 20,252 patients. Int J Cardiol.
2015;190:384-8. doi: 10.1016/j.ijcard.2015.04.191. Epub 2015 Apr 24. PubMed PMID:
25967701.


20: 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.