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MedKoo Cat#: 317770 | Name: Enalapril Maleate
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Description:

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

Enalapril maleate is an effective and potent angiotensin-converting enzyme inhibitor that is used to treat hypertension and heart failure. The compound has been used to study diabetic angiopathy in diabetic rats and inhibition of ACE in hog plasma. ACE inhibitors disturb the enin-angiotensin- aldosterone system. As a prodrug, enalapril is converted by de-esterification into its active form enalaprilat. Enalaprilat competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Enalapril also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.

Chemical Structure

Enalapril Maleate
Enalapril Maleate
CAS#76095-16-4 (maleate)

Theoretical Analysis

MedKoo Cat#: 317770

Name: Enalapril Maleate

CAS#: 76095-16-4 (maleate)

Chemical Formula: C24H32N2O9

Exact Mass: 0.0000

Molecular Weight: 492.52

Elemental Analysis: C, 58.53; H, 6.55; N, 5.69; O, 29.24

Price and Availability

Size Price Availability Quantity
1g USD 265.00 2 Weeks
5g USD 650.00 2 Weeks
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Related CAS #
75847-73-3 (free acid) 76095-16-4 (maleate) 149404-21-7 (sodium)
Synonym
Enalapril Maleate; Renitec; Glioten; Vasotec; Baripril; Maleate, Enalapril; MK 421; MK-421; MK421; Renitec; Renitek; Xanef;
IUPAC/Chemical Name
(Z)-but-2-enedioic acid;(2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid
InChi Key
OYFJQPXVCSSHAI-QFPUQLAESA-N
InChi Code
InChI=1S/C20H28N2O5.C4H4O4/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25;5-3(6)1-2-4(7)8/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,16-,17-;/m0./s1
SMILES Code
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)O.C(=C\C(=O)O)\C(=O)O
Appearance
White to off-white crystalline 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
Instruction
View handling instruction
Biological target:
Enalapril (maleate) (MK-421 (maleate)), the active metabolite of enalapril, is an angiotensin-converting enzyme (ACE) inhibitor.
In vitro activity:
Enalapril significantly inhibited LPS-induced IκBα phosphorylation/degradation, NF-κB binding activity, and pro-inflammatory cytokine production in both IEC and peritoneal macrophages. The administration of enalapril significantly reduced the severity of colitis, as assessed based on histology in both murine colitis models. Furthermore, in colon tissue, the up-regulation of IκBα phosphorylation with colitis induction was attenuated in enalapril-treated mice. Reference: Life Sci. 2014 Jan 24;95(1):29-39. https://pubmed.ncbi.nlm.nih.gov/24239644/
In vivo activity:
Enalapril (ENAL) was efficient in decreasing steatosis in mice fed a hyperlipidemic diet, histological observation of hepatic tissue showed a considerable increase of dispersed fat droplets in the liver of HF animals and a statistically significant lower mean in the HF + ENAL group (p = 0.0123) (Fig. 3D; E). Reference: Prostaglandins Other Lipid Mediat. 2021 Feb;152:106501. https://pubmed.ncbi.nlm.nih.gov/33049402/
Solvent mg/mL mM
Solubility
DMSO 37.5 76.14
DMF 15.0 30.46
Ethanol 0.3 0.51
PBS (pH 7.2) 1.0 2.03
Water 33.3 67.67
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 492.52 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. Laham HZ, Khabour OF, Alzoubi KH, Sadiq MF. Enalapril protect human lymphocytes from genotoxicity of Hydrochlorothiazide. Pak J Pharm Sci. 2019 Nov;32(6):2667-2671. PMID: 31969300. 2. Lee C, Chun J, Hwang SW, Kang SJ, Im JP, Kim JS. Enalapril inhibits nuclear factor-κB signaling in intestinal epithelial cells and peritoneal macrophages and attenuates experimental colitis in mice. Life Sci. 2014 Jan 24;95(1):29-39. doi: 10.1016/j.lfs.2013.11.005. Epub 2013 Nov 15. PMID: 24239644. 3. Moraes DS, Lelis DF, Andrade JMO, Meyer L, Guimarães ALS, De Paula AMB, Farias LC, Santos SHS. Enalapril improves obesity associated liver injury ameliorating systemic metabolic markers by modulating Angiotensin Converting Enzymes ACE/ACE2 expression in high-fat feed mice. Prostaglandins Other Lipid Mediat. 2021 Feb;152:106501. doi: 10.1016/j.prostaglandins.2020.106501. Epub 2020 Oct 10. PMID: 33049402. 4. Ma H, Zhang Q, Shi J, Gao Y, Sun C, Zhang W. Enalapril inhibits inflammatory osteolysis induced by wear debris in a mouse model. J Int Med Res. 2020 Jun;48(6):300060520931612. doi: 10.1177/0300060520931612. PMID: 32552231; PMCID: PMC7303775.
In vitro protocol:
1. Laham HZ, Khabour OF, Alzoubi KH, Sadiq MF. Enalapril protect human lymphocytes from genotoxicity of Hydrochlorothiazide. Pak J Pharm Sci. 2019 Nov;32(6):2667-2671. PMID: 31969300. 2. Lee C, Chun J, Hwang SW, Kang SJ, Im JP, Kim JS. Enalapril inhibits nuclear factor-κB signaling in intestinal epithelial cells and peritoneal macrophages and attenuates experimental colitis in mice. Life Sci. 2014 Jan 24;95(1):29-39. doi: 10.1016/j.lfs.2013.11.005. Epub 2013 Nov 15. PMID: 24239644.
In vivo protocol:
1. Moraes DS, Lelis DF, Andrade JMO, Meyer L, Guimarães ALS, De Paula AMB, Farias LC, Santos SHS. Enalapril improves obesity associated liver injury ameliorating systemic metabolic markers by modulating Angiotensin Converting Enzymes ACE/ACE2 expression in high-fat feed mice. Prostaglandins Other Lipid Mediat. 2021 Feb;152:106501. doi: 10.1016/j.prostaglandins.2020.106501. Epub 2020 Oct 10. PMID: 33049402. 2. Ma H, Zhang Q, Shi J, Gao Y, Sun C, Zhang W. Enalapril inhibits inflammatory osteolysis induced by wear debris in a mouse model. J Int Med Res. 2020 Jun;48(6):300060520931612. doi: 10.1177/0300060520931612. PMID: 32552231; PMCID: PMC7303775.
1: Aygen B, Kucuksu M, Aydin S, Ozercan IH. Effect of enalapril maleate on ghrelin levels in metabolic syndrome in rats. Peptides. 2015 May;67:39-44. doi: 10.1016/j.peptides.2015.03.002. Epub 2015 Mar 14. PubMed PMID: 25784288. 2: de Oliveira AP, Cunha TA, Serpa RC, Taveira SF, Lima EM, Almeida Diniz DG, de Freitas LA, Marreto RN. Improvement of enalapril maleate chemical stability by high shear melting granulation. Pharm Dev Technol. 2014 Sep 18:1-7. [Epub ahead of print] PubMed PMID: 25231642. 3: Ramírez-Rigo MV, Olivera ME, Rubio M, Manzo RH. Enhanced intestinal permeability and oral bioavailability of enalapril maleate upon complexation with the cationic polymethacrylate Eudragit E100. Eur J Pharm Sci. 2014 May 13;55:1-11. doi: 10.1016/j.ejps.2014.01.001. Epub 2014 Jan 20. PubMed PMID: 24456933. 4: Chen J, Zhang LH, Xu RJ, Bu NJ, Zhang L. Proposal of a new degradation mechanism of enalapril maleate and improvement of enalapril maleate stability in tablet formulation with different stabilizers. Pharmazie. 2014 Apr;69(4):277-80. PubMed PMID: 24791591. 5: Matsuura-Hachiya Y, Arai KY, Ozeki R, Kikuta A, Nishiyama T. Angiotensin-converting enzyme inhibitor (enalapril maleate) accelerates recovery of mouse skin from UVB-induced wrinkles. Biochem Biophys Res Commun. 2013 Dec 6;442(1-2):38-43. doi: 10.1016/j.bbrc.2013.10.162. Epub 2013 Nov 8. PubMed PMID: 24216112. 6: Vehovec T, Gartner A, Planinšek O, Obreza A. Influence of different types of commercially available microcrystalline cellulose on degradation of perindopril erbumine and enalapril maleate in binary mixtures. Acta Pharm. 2012 Dec;62(4):515-28. doi: 10.2478/v10007-012-0039-5. PubMed PMID: 23333887. 7: Hartung A, Knoell M, Schmidt U, Langguth P. Relevance of air-to-liquid mass ratio effect on final granule properties of an Enalapril maleate formulation. Drug Dev Ind Pharm. 2012 Jan;38(1):12-8. doi: 10.3109/03639045.2011.589451. Epub 2011 Jul 1. PubMed PMID: 21721850. 8: Bibi R, Naqvi BS, Shoaib MH, Rahim N. Design and evaluation of a new formulation of enalapril maleate tablet. Pak J Pharm Sci. 2011 Apr;24(2):211-5. PubMed PMID: 21454172. 9: Semalty A, Semalty M, Nautiyal U. Formulation and evaluation of mucoadhesive buccal films of enalapril maleate. Indian J Pharm Sci. 2010 Sep;72(5):571-5. doi: 10.4103/0250-474X.78522. PubMed PMID: 21694987; PubMed Central PMCID: PMC3116300. 10: Toporisic R, Mlakar A, Hvala J, Prislan I, Zupancic-Kralj L. Identification of new impurities of enalapril maleate on oxidation in the presence of magnesium monoperoxyphthalate. J Pharm Biomed Anal. 2010 Jun 5;52(2):294-9. doi: 10.1016/j.jpba.2009.12.018. Epub 2009 Dec 29. PubMed PMID: 20122808. 11: Loftsson T, Thorisdóttir S, Fridriksdóttir H, Stefánsson E. Enalaprilat and enalapril maleate eyedrops lower intraocular pressure in rabbits. Acta Ophthalmol. 2010 May;88(3):337-41. doi: 10.1111/j.1755-3768.2008.01495.x. Epub 2009 Apr 29. PubMed PMID: 19432862. 12: Lopes RA, Neves Fde A. Meta-analysis for bioequivalence studies: interchangeability of generic drugs and similar containing Hydrochlorothiazide is possible but not with Enalapril Maleate. J Bras Nefrol. 2010 Apr-Jun;32(2):173-81. English, Portuguese. PubMed PMID: 21103677. 13: Nair AB, Vyas H, Kumar A. Controlled release matrix uncoated tablets of enalapril maleate using hpmc alone. J Basic Clin Pharm. 2010 Mar;1(2):71-5. Epub 2010 May 15. PubMed PMID: 24825968; PubMed Central PMCID: PMC3979173. 14: Al-Arfaj NA, Al-Abdulkareem EA, Aly FA. Determination of enalapril maleate and atenolol in their pharmaceutical products and in biological fluids by flow-injection chemiluminescence. Luminescence. 2009 Nov-Dec;24(6):422-8. doi: 10.1002/bio.1129. PubMed PMID: 19455718. 15: Sosnowska K, Winnicka K, Czajkowska-Kośnik A. Stability of extemporaneous enalapril maleate suspensions for pediatric use prepared from commercially available tablets. Acta Pol Pharm. 2009 May-Jun;66(3):321-6. PubMed PMID: 19645333. 16: Zhao F, Li JP, Wang SY, Guan DM, Ge JB, Hu J, Wang YN, Zhang FM, Huo Y. [The effect of baseline homocysteine level on the efficacy of enalapril maleate and folic acid tablet in lowering blood pressure and plasma homocysteine]. Zhonghua Yi Xue Za Zhi. 2008 Nov 18;88(42):2957-61. Chinese. PubMed PMID: 19080072. 17: Yamane T, Fujii Y, Orito K, Osamura K, Kanai T, Wakao Y. Comparison of the effects of candesartan cilexetil and enalapril maleate on right ventricular myocardial remodeling in dogs with experimentally induced pulmonary stenosis. Am J Vet Res. 2008 Dec;69(12):1574-9. doi: 10.2460/ajvr.69.12.1574. PubMed PMID: 19046003. 18: Baraka MM, El-Sadek M, Moussa EM, Abd-Alaty NM. Spectrophotometric and atomic absorption determination of ramipril, enalapril maleate and fosinopril through ternary complex formation with molybdenum (V)-thiocyanate (Mo(V)-SCN). Chem Pharm Bull (Tokyo). 2008 Nov;56(11):1521-7. PubMed PMID: 18981600. 19: Lima DM, dos Santos LD, Lima EM. Stability and in vitro release profile of enalapril maleate from different commercially available tablets: possible therapeutic implications. J Pharm Biomed Anal. 2008 Aug 5;47(4-5):934-7. doi: 10.1016/j.jpba.2008.02.030. Epub 2008 Mar 4. PubMed PMID: 18472382. 20: Zhang BQ, Huang YS, Zhang JP, Zhang DX, Dang YM, Wang G, Hu JY, Lei ZY, Xiao R. [Protective effects of administration of enalapril maleate on rat myocardial damage in early stage of burns]. Zhonghua Shao Shang Za Zhi. 2007 Oct;23(5):335-8. Chinese. PubMed PMID: 18396757.