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MedKoo Cat#: 561619 | Name: Delapril

Description:

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

Delapril is an angiotensin-converting enzyme (ACE) inhibitor that blocks the conversion of angiotensin I to angiotensin II.

Chemical Structure

Delapril
Delapril
CAS#83435-66-9 (free)

Theoretical Analysis

MedKoo Cat#: 561619

Name: Delapril

CAS#: 83435-66-9 (free)

Chemical Formula: C26H32N2O5

Exact Mass: 452.2311

Molecular Weight: 452.55

Elemental Analysis: C, 69.01; H, 7.13; N, 6.19; O, 17.68

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Related CAS #
83435-67-0 (HCl) 83435-66-9 (free)
Synonym
Delapril; Alindapril; Delaprilum; Delaket; CV-3317; CV3317; CV 3317;
IUPAC/Chemical Name
2-[2,3-Dihydro-1H-inden-2-yl-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]amino]acetic acid
InChi Key
WOUOLAUOZXOLJQ-MBSDFSHPSA-N
InChi Code
InChI=1S/C26H32N2O5/c1-3-33-26(32)23(14-13-19-9-5-4-6-10-19)27-18(2)25(31)28(17-24(29)30)22-15-20-11-7-8-12-21(20)16-22/h4-12,18,22-23,27H,3,13-17H2,1-2H3,(H,29,30)/t18-,23-/m0/s1
SMILES Code
O=C(O)CN(C1CC2=C(C=CC=C2)C1)C([C@@H](N[C@@H](CCC3=CC=CC=C3)C(OCC)=O)C)=O
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:
Delapril is an ACE inhibitor indicated in the treatment of essential hypertension.
In vitro activity:
The effect of delapril on cardiomyocytes isolated from the non-infarcted area comprised of viable cells subjected to cardiac remodeling following the MI (myocardial infarction) was investigated. In unloaded intact single cardiomyocytes from MI mice (vs. Sham), sarcomere length (SL) shortening, reflecting cell contraction during field stimulation, was decreased (Fig. 2A,B). Contraction and relaxation velocities were also reduced (Fig. 2C). Delapril treatment prevented all of these changes. Diastolic Ca2+ using the ratiometric indicator indo-1 was further investigated. Diastolic Ca2+ was higher in MI mice than in Sham mice, an increase that was completely prevented by delapril (Fig. 3C).Delapril treatment thus, had a notable effect on cell relaxation, Ca2+-transient decay and diastolic Ca2+. Delapril treatment had a powerful preventive effect on changes in both maximal active tension and myofilament Ca2+ sensitivity (pCa50: 5.74±0.02, n=22; P<0.05 for MI-D vs. MI). Delapril treatment had no effect on the reduction of SERCA2a abundance but remarkably, prevented the increase of PLB protein and phosphorylation levels. In conclusion, early therapy with delapril after MI preserved the normal contraction/relaxation cycle of surviving cardiomyocytes. Reference: Curr Mol Med. 2012 Feb; 12(2): 206–217. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3472404/
In vivo activity:
The effects of the ACE-I delapril on cardiomyocytes in a mouse model of heart failure (HF) after MI (myocardial infarction) were investigated. Mice were randomly assigned to three groups: Sham, MI, and MI-D (6 weeks of treatment with a non-hypotensive dose of delapril started 24h after MI). Delapril maintained cardiomyocyte contraction and relaxation, prevented diastolic Ca2+ overload and retained the normal Ca2+ sensitivity of contractile proteins. Delapril maintained SERCA2a activity through normalization of PPLB/PLB (for both Ser16-PLB and Thr17-PLB) and PLB/SERCA2a ratios in cardiomyocytes, favoring normal reuptake of Ca2+ in the sarcoplasmic reticulum. In addition, delapril prevented defective cTnI function by normalizing the expression of PKC, enhanced in MI mice. In conclusion, early therapy with delapril after MI preserved the normal contraction/relaxation cycle of surviving cardiomyocytes with multiple direct effects on key intracellular mechanisms contributing to preserve cardiac function. Reference: Curr Mol Med. 2012 Feb; 12(2): 206–217. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3472404/
Solvent mg/mL mM
Solubility
H2O 0.0 0.01
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 452.55 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. Zalvidea S, André L, Loyer X, Cassan C, Sainte-Marie Y, Thireau J, Sjaastad I, Heymes C, Pasquié JL, Cazorla O, Aimond F, Richard S. ACE inhibition prevents diastolic Ca2+ overload and loss of myofilament Ca2+ sensitivity after myocardial infarction. Curr Mol Med. 2012 Feb;12(2):206-17. doi: 10.2174/156652412798889045. PMID: 22280358; PMCID: PMC3472404. 2. Ichihara A, Hayashi M, Hirota N, Okada H, Koura Y, Tada Y, Kaneshiro Y, Tsuganezawa H, Saruta T. Angiotensin II type 2 receptor inhibits prorenin processing in juxtaglomerular cells. Hypertens Res. 2003 Nov;26(11):915-21. doi: 10.1291/hypres.26.915. PMID: 14714584. 3. Ichihara A, Hayashi M, Hirota N, Okada H, Koura Y, Tada Y, Kaneshiro Y, Tsuganezawa H, Saruta T. Angiotensin II type 2 receptor inhibits prorenin processing in juxtaglomerular cells. Hypertens Res. 2003 Nov;26(11):915-21. doi: 10.1291/hypres.26.915. PMID: 14714584.
In vitro protocol:
1. Zalvidea S, André L, Loyer X, Cassan C, Sainte-Marie Y, Thireau J, Sjaastad I, Heymes C, Pasquié JL, Cazorla O, Aimond F, Richard S. ACE inhibition prevents diastolic Ca2+ overload and loss of myofilament Ca2+ sensitivity after myocardial infarction. Curr Mol Med. 2012 Feb;12(2):206-17. doi: 10.2174/156652412798889045. PMID: 22280358; PMCID: PMC3472404. 2. Ichihara A, Hayashi M, Hirota N, Okada H, Koura Y, Tada Y, Kaneshiro Y, Tsuganezawa H, Saruta T. Angiotensin II type 2 receptor inhibits prorenin processing in juxtaglomerular cells. Hypertens Res. 2003 Nov;26(11):915-21. doi: 10.1291/hypres.26.915. PMID: 14714584.
In vivo protocol:
1. Zalvidea S, André L, Loyer X, Cassan C, Sainte-Marie Y, Thireau J, Sjaastad I, Heymes C, Pasquié JL, Cazorla O, Aimond F, Richard S. ACE inhibition prevents diastolic Ca2+ overload and loss of myofilament Ca2+ sensitivity after myocardial infarction. Curr Mol Med. 2012 Feb;12(2):206-17. doi: 10.2174/156652412798889045. PMID: 22280358; PMCID: PMC3472404. 2. Nakaya H, Sasamura H, Hayashi M, Saruta T. Temporary treatment of prepubescent rats with angiotensin inhibitors suppresses the development of hypertensive nephrosclerosis. J Am Soc Nephrol. 2001 Apr;12(4):659-666. doi: 10.1681/ASN.V124659. PMID: 11274226.
1: González-Juanatey JR, Cordero A. Benefits of delapril in hypertensive patients along the cardiovascular continuum. Expert Rev Cardiovasc Ther. 2013 Mar;11(3):271-81. doi: 10.1586/erc.12.188. PMID: 23469905. 2: Cavalieri L, Cremonesi G. Delapril plus indapamide: a review of the combination in the treatment of hypertension. Clin Drug Investig. 2007;27(6):367-80. doi: 10.2165/00044011-200727060-00001. PMID: 17506588. 3: McCormack PL, Keating GM. Delapril/manidipine. Drugs. 2006;66(7):961-9. doi: 10.2165/00003495-200666070-00014. PMID: 16740017. 4: Fogari R, Mugellini A, Circelli M, Cremonesi G. Combination delapril/manidipine as antihypertensive therapy in high-risk patients. Clin Drug Investig. 2011;31(7):439-53. doi: 10.2165/11589000-000000000-00000. PMID: 21627336. 5: Razzetti R, Acerbi D. Pharmacokinetic and pharmacologic properties of delapril, a lipophilic nonsulfhydryl angiotensin-converting enzyme inhibitor. Am J Cardiol. 1995 Jun 16;75(18):7F-12F. doi: 10.1016/s0002-9149(99)80508-6. PMID: 7778536. 6: Otero ML. Manidipine-delapril combination in the management of hypertension. Vasc Health Risk Manag. 2007;3(3):255-63. PMID: 17703633; PMCID: PMC2293964. 7: Kahan T, Ambrosioni E. Delapril/manidipine: viewpoints. Drugs. 2006;66(7):970-1. doi: 10.2165/00003495-200666070-00016. PMID: 16740019. 8: Coca A. Manidipine plus delapril in patients with Type 2 diabetes and hypertension: reducing cardiovascular risk and end-organ damage. Expert Rev Cardiovasc Ther. 2007 Mar;5(2):147-59. doi: 10.1586/14779072.5.2.147. PMID: 17338661. 9: Saruta T, Nishikawa K. Characteristics of a new angiotensin converting enzyme inhibitor: delapril. Am J Hypertens. 1991 Jan;4(1 Pt 2):23S-28S. doi: 10.1093/ajh/4.1.23s. PMID: 2009144. 10: Shiba T, Inoue M, Tada H, Hayashi Y, Okuda Y, Fujita R, Makino F, Takahasi C, Kageyama S, Kitamura S, Iwamoto Y. Delapril versus manidipine in hypertensive therapy to halt the type-2-diabetes-mellitus-associated nephropathy. Diabetes Res Clin Pract. 2000 Feb;47(2):97-104. doi: 10.1016/s0168-8227(99)00114-x. PMID: 10670908. 11: Shionoiri H, Yasuda G, Ikeda A, Ohta T, Miyajima E, Kaneko Y. Pharmacokinetics and depressor effect of delapril in patients with essential hypertension. Clin Pharmacol Ther. 1987 Jan;41(1):74-9. doi: 10.1038/clpt.1987.12. PMID: 3802709. 12: Thireau J, Zalvidea S, Meschin P, Pasquie JL, Aimond F, Richard S. ACE Inhibitor Delapril Prevents Ca(2+)-Dependent Blunting of IK1 and Ventricular Arrhythmia in Ischemic Heart Disease. Curr Mol Med. 2015;15(7):642-51. doi: 10.2174/1566524015666150831131459. PMID: 26321755. 13: Mugellini A, Preti P, Zoppi A, Corradi L, Fogari E, Derosa G, Fogari R. Effect of delapril-manidipine combination vs irbesartan-hydrochlorothiazide combination on fibrinolytic function in hypertensive patients with type II diabetes mellitus. J Hum Hypertens. 2004 Oct;18(10):687-91. doi: 10.1038/sj.jhh.1001726. PMID: 15071488. 14: Fogari R, Derosa G, Zoppi A, Lazzari P, Corradi L, Preti P, Mugellini A. Effect of delapril/manidipine vs olmesartan/ hydrochlorothiazide combination on insulin sensitivity and fibrinogen in obese hypertensive patients. Intern Med. 2008;47(5):361-6. doi: 10.2169/internalmedicine.47.0449. Epub 2008 Mar 3. PMID: 18310964. 15: Mugellini A, Dobovisek J, Planinc D, Cremonesi G, Fogari R. Efficacy and safety of delapril plus manidipine compared with enalapril plus hydrochlorothiazide in mild to moderate essential hypertension: results of a randomized trial. Clin Ther. 2004 Sep;26(9):1419-26. doi: 10.1016/j.clinthera.2004.09.018. PMID: 15531004. 16: Suzuki S, Ohtomo M, Satoh Y, Kawasaki H, Hirai M, Hirai A, Hirai S, Onoda M, Hinokio Y, Akai H, Toyota T. Effect of manidipine and delapril on insulin sensitivity in type 2 diabetic patients with essential hypertension. Diabetes Res Clin Pract. 1996 Jun;33(1):43-51. doi: 10.1016/0168-8227(96)01273-9. PMID: 8877275. 17: Boschi S, Vantaggiato G, Torri C, Zini I, Agnati LF, Zoli M, Biagini G. Protective effects of delapril combined with indapamide or hydrochlorothiazide in spontaneously hypertensive stroke-prone rats: a comparative dose-response analysis. J Cardiovasc Pharmacol. 2000 Sep;36(3):321-8. doi: 10.1097/00005344-200009000-00007. PMID: 10975589. 18: Mizuno K, Tani M, Niimura S, Yamaguchi M, Inagami T, Fukuchi S. The antihypertensive mechanism of delapril, a newly developed converting enzyme inhibitor, is related to the suppression of vascular angiotensin II release in the spontaneously hypertensive rat. Am J Hypertens. 1991 Jan;4(1 Pt 2):60S-66S. doi: 10.1093/ajh/4.1.60s. PMID: 2009151. 19: Ogihara T, Kaneko Y, Ikeda M, Yamada K, Omae T, Arakawa K, Ishii M, Yoshinaga K, Kumahara Y, Kokubu T. Clinical evaluation of delapril in Japan. Report from the Japan Study Group on Delapril. Am J Hypertens. 1991 Jan;4(1 Pt 2):42S-45S. doi: 10.1093/ajh/4.1.42s. PMID: 2009147. 20: Todeschini V, Sangoi Mda S, Volpato NM. Delapril and manidipine measurements by liquid chromatography-tandem mass spectrometry in a pharmaceutical formulation. Eur J Mass Spectrom (Chichester). 2011;17(3):287-96. doi: 10.1255/ejms.1128. PMID: 21828421.

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