Ramipril
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MedKoo CAT#: 318650

CAS#: 87333-19-5

Description: Ramipril, also known as HOE-498. is an inhibitor of the angiotensin- converting enzyme (ACE) that is reported to quickly hydrolyze into its active metabolite, Ramiprilat.

Chemical Structure

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Ramipril
CAS# 87333-19-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318650
Name: Ramipril
CAS#: 87333-19-5
Chemical Formula: C23H32N2O5
Exact Mass: 416.23
Molecular Weight: 416.510
Elemental Analysis: C, 66.32; H, 7.74; N, 6.73; O, 19.21

Price and Availability

Size Price Availability Quantity
500mg USD 300
1g USD 450
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Synonym: Ramipril; Tritace; Altace; Carasel; Ramace; Zabien; HOE-498; HOE498; Hoechst Brand of Ramipril; Monarch Brand of Ramipril; Promed Brand of Ramipril; Ramace; Ramipril; Triatec ; Tritace; Vesdil;

IUPAC/Chemical Name: (2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid

InChi Key: HDACQVRGBOVJII-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)

SMILES Code: O=C([C@@H]1C[C@@](CCC2)([H])[C@@]2([H])N1C([C@@H](N[C@H](C(OCC)=O)CCC3=CC=CC=C3)C)=O)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 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: Ramipril is an ACE inhibitor with IC50 of 5 nM. Ramipril enhances the activity of ACE-associated CK2 and the phosphorylation of ACE Ser1270 in cultured endothelial cell. Prolonged Ramipril treatment increases ACE expression in primary cultures of human endothelial cells and in vivo (mouse lung).
In vitro activity: Prolonged ramiprilat treatment increased ACE expression in primary cultures of human endothelial cells and in vivo (mouse lung), a response that was prevented by pretreatment with the JNK inhibitor SP600125. ACE is involved in outside-in signaling in endothelial cells. Reference: Circ Res. 2004 Jan 9;94(1):60-7. https://pubmed.ncbi.nlm.nih.gov/14615289/
In vivo activity: Ramipril prevented the functional and morphological alterations in paclitaxel mice. This work highlights the potential of ramipril as a novel preventive treatment for paclitaxel-induced peripheral neuropathy, and suggests there is involvement of angiotensin II type 2 receptorin the neuroprotective role of ramipril in paclitaxel-induced peripheral neuropathy. Reference: Pharmaceutics. 2022 Apr 12;14(4):848. https://pubmed.ncbi.nlm.nih.gov/35456682/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 1.0 2.40

Preparing Stock Solutions

The following data is based on the product molecular weight 416.51 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. Kohlstedt K, Brandes RP, Müller-Esterl W, Busse R, Fleming I. Angiotensin-converting enzyme is involved in outside-in signaling in endothelial cells. Circ Res. 2004 Jan 9;94(1):60-7. doi: 10.1161/01.RES.0000107195.13573.E4. Epub 2003 Nov 13. PMID: 14615289. 2. Ceconi C, Francolini G, Bastianon D, Gitti GL, Comini L, Ferrari R. Differences in the effect of angiotensin-converting enzyme inhibitors on the rate of endothelial cell apoptosis: in vitro and in vivo studies. Cardiovasc Drugs Ther. 2007 Dec;21(6):423-9. doi: 10.1007/s10557-007-6068-5. Epub 2007 Nov 15. PMID: 18004652. 3. Ateya AM, El Hakim I, Shahin SM, El Borolossy R, Kreutz R, Sabri NA. Effects of Ramipril on Biomarkers of Endothelial Dysfunction and Inflammation in Hypertensive Children on Maintenance Hemodialysis: the SEARCH Randomized Placebo-Controlled Trial. Hypertension. 2022 Aug;79(8):1856-1865. doi: 10.1161/HYPERTENSIONAHA.122.19312. Epub 2022 Jun 10. PMID: 35686561. 4. Bouchenaki H, Bernard A, Bessaguet F, Frachet S, Richard L, Sturtz F, Magy L, Bourthoumieu S, Demiot C, Danigo A. Neuroprotective Effect of Ramipril Is Mediated by AT2 in a Mouse MODEL of Paclitaxel-Induced Peripheral Neuropathy. Pharmaceutics. 2022 Apr 12;14(4):848. doi: 10.3390/pharmaceutics14040848. PMID: 35456682; PMCID: PMC9030366.
In vitro protocol: 1. Kohlstedt K, Brandes RP, Müller-Esterl W, Busse R, Fleming I. Angiotensin-converting enzyme is involved in outside-in signaling in endothelial cells. Circ Res. 2004 Jan 9;94(1):60-7. doi: 10.1161/01.RES.0000107195.13573.E4. Epub 2003 Nov 13. PMID: 14615289. 2. Ceconi C, Francolini G, Bastianon D, Gitti GL, Comini L, Ferrari R. Differences in the effect of angiotensin-converting enzyme inhibitors on the rate of endothelial cell apoptosis: in vitro and in vivo studies. Cardiovasc Drugs Ther. 2007 Dec;21(6):423-9. doi: 10.1007/s10557-007-6068-5. Epub 2007 Nov 15. PMID: 18004652.
In vivo protocol: 1. Ateya AM, El Hakim I, Shahin SM, El Borolossy R, Kreutz R, Sabri NA. Effects of Ramipril on Biomarkers of Endothelial Dysfunction and Inflammation in Hypertensive Children on Maintenance Hemodialysis: the SEARCH Randomized Placebo-Controlled Trial. Hypertension. 2022 Aug;79(8):1856-1865. doi: 10.1161/HYPERTENSIONAHA.122.19312. Epub 2022 Jun 10. PMID: 35686561. 2. Bouchenaki H, Bernard A, Bessaguet F, Frachet S, Richard L, Sturtz F, Magy L, Bourthoumieu S, Demiot C, Danigo A. Neuroprotective Effect of Ramipril Is Mediated by AT2 in a Mouse MODEL of Paclitaxel-Induced Peripheral Neuropathy. Pharmaceutics. 2022 Apr 12;14(4):848. doi: 10.3390/pharmaceutics14040848. PMID: 35456682; PMCID: PMC9030366.

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1: Borghi C, Omboni S, Novo S, Vinereanu D, Ambrosio G, Ambrosioni E; SMILE-4
Working Party. Zofenopril and Ramipril in Combination with Acetyl Salicylic Acid
in Postmyocardial Infarction Patients with Left Ventricular Systolic Dysfunction:
A Retrospective Analysis of the SMILE-4 Randomized, Double-Blind Study in
Diabetic Patients. Cardiovasc Ther. 2016 Apr;34(2):76-84. doi:
10.1111/1755-5922.12175. PubMed PMID: 26789425.


2: Knoll GA, Fergusson D, Chassé M, Hebert P, Wells G, Tibbles LA, Treleaven D,
Holland D, White C, Muirhead N, Cantarovich M, Paquet M, Kiberd B, Gourishankar
S, Shapiro J, Prasad R, Cole E, Pilmore H, Cronin V, Hogan D, Ramsay T, Gill J.
Ramipril versus placebo in kidney transplant patients with proteinuria: a
multicentre, double-blind, randomised controlled trial. Lancet Diabetes
Endocrinol. 2016 Apr;4(4):318-26. doi: 10.1016/S2213-8587(15)00368-X. Epub 2015
Oct 23. PubMed PMID: 26608067.


3: Serrano-Rodríguez JM, Gómez-Díez M, Esgueva M, Castejón-Riber C, Mena-Bravo A,
Priego-Capote F, Serrano Caballero JM, Muñoz A. Pharmacokinetics and
pharmacodynamics of ramipril and ramiprilat after intravenous and oral doses of
ramipril in healthy horses. Vet J. 2016 Feb;208:38-43. doi:
10.1016/j.tvjl.2015.10.024. Epub 2015 Oct 23. PubMed PMID: 26639833.


4: Sheik Uduman MS, Reddy RB, Punuru P, Chakka G, Karunakaran G. Protective Role
of Ramipril and Candesartan against Myocardial Ischemic Reperfusion Injury: A
Biochemical and Transmission Electron Microscopical Study. Adv Pharmacol Sci.
2016;2016:4608979. doi: 10.1155/2016/4608979. Epub 2016 Mar 6. PubMed PMID:
27042175; PubMed Central PMCID: PMC4799827.


5: Marinšek M, Sinkovič A. Ramipril and Losartan Exert a Similar Long-Term Effect
upon Markers of Heart Failure, Endogenous Fibrinolysis, and Platelet Aggregation
in Survivors of ST-Elevation Myocardial Infarction: A Single Centre Randomized
Trial. Biomed Res Int. 2016;2016:9040457. doi: 10.1155/2016/9040457. Epub 2016
Mar 15. PubMed PMID: 27064499; PubMed Central PMCID: PMC4811062.


6: 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.


7: Cianfrone P, Simeoni M, Comi N, Piraina V, Talarico R, Cerantonio A, Gentile
I, Fabiano FF, Lucisano G, Foti D, Gulletta E, Fuiano G. How to improve duration
and efficiency of the antiproteinuric response to Ramipril: RamiPROT-a
prospective cohort study. J Nephrol. 2015 Dec 26. [Epub ahead of print] PubMed
PMID: 26707494.


8: Notice of Retraction: Ramipril Markedly Improves Walking Ability in Patients
With Peripheral Arterial Disease. Ann Intern Med. 2015 Dec 1;163(11):884. doi:
10.7326/M15-2625. Epub 2015 Nov 6. PubMed PMID: 26544086.


9: Mandelbrot DA, Alberú J, Barama A, Marder BA, Silva HT Jr, Flechner SM, Flynn
A, Healy C, Li H, Tortorici MA, Schulman SL. Effect of Ramipril on Urinary
Protein Excretion in Maintenance Renal Transplant Patients Converted to
Sirolimus. Am J Transplant. 2015 Dec;15(12):3174-84. doi: 10.1111/ajt.13384. Epub
2015 Jul 14. PubMed PMID: 26176342.


10: Bramlage P, Schmieder RE, Gitt AK, Baumgart P, Mahfoud F, Buhck H, Ouarrak T,
Ehmen M, Potthoff SA; EARLY Registry Group. The renin-angiotensin receptor
blocker azilsartan medoxomil compared with the angiotensin-converting enzyme
inhibitor ramipril in clinical trials versus routine practice: insights from the
prospective EARLY registry. Trials. 2015 Dec 19;16:581. doi:
10.1186/s13063-015-1100-8. PubMed PMID: 26686682; PubMed Central PMCID:
PMC4684935.


11: Kim MH, Kang HM, Kim CE, Han S, Kim SW. Ramipril inhibits high
glucose-stimulated up-regulation of adhesion molecules via the ERK1/2 MAPK
signaling pathway in human umbilical vein endothelial cells. Cell Mol Biol Lett.
2015 Dec 1;20(5):937-47. doi: 10.1515/cmble-2015-0053. PubMed PMID: 26636413.


12: Hsing SC, Lu KC, Sun CA, Chien WC, Chung CH, Kao SY. The Association of
Losartan and Ramipril Therapy With Kidney and Cardiovascular Outcomes in Patients
With Chronic Kidney Disease: A Chinese Nation-Wide Cohort Study in Taiwan.
Medicine (Baltimore). 2015 Dec;94(48):e1999. doi: 10.1097/MD.0000000000001999.
PubMed PMID: 26632888; PubMed Central PMCID: PMC4674191.


13: Notice of Retraction: Ramipril Markedly Improves Walking Ability in Patients
With Peripheral Arterial Disease [Summary for Patients]. Ann Intern Med. 2015 Dec
1;163(11):884. doi: 10.7326/M15-2647. Epub 2015 Nov 6. PubMed PMID: 26544534.


14: Imbalzano E, Scarpelli M, Mandraffino G, Creazzo M, Lizio G, Trapani G,
Dattilo G, Dalbeni A, Tomasello C, Sardo MA, Saitta A. Combination therapy with
aliskiren versus ramipril or losartan added to conventional therapy in patients
with type 2 diabetes mellitus, uncontrolled hypertension and microalbuminuria. J
Renin Angiotensin Aldosterone Syst. 2015 Dec;16(4):956-64. doi:
10.1177/1470320314530018. Epub 2014 Jul 27. PubMed PMID: 25070350.


15: Notice of Retraction: Ahimastos AA, et al. Effect of Ramipril on Walking
Times and Quality of Life Among Patients With Peripheral Artery Disease and
Intermittent Claudication: A Randomized Controlled Trial. JAMA.
2013;309(5):453-460. JAMA. 2015 Oct 13;314(14):1520-1. doi:
10.1001/jama.2015.10811. PubMed PMID: 26367349.


16: Fahmy Wahba MG, Shehata Messiha BA, Abo-Saif AA. Ramipril and haloperidol as
promising approaches in managing rheumatoid arthritis in rats. Eur J Pharmacol.
2015 Oct 15;765:307-15. doi: 10.1016/j.ejphar.2015.08.026. Epub 2015 Aug 21.
PubMed PMID: 26302059.


17: McCarthy M. Ramipril research papers are retracted over faked data. BMJ. 2015
Sep 21;351:h5035. doi: 10.1136/bmj.h5035. PubMed PMID: 26391363.


18: Bull S, Loudon M, Francis JM, Joseph J, Gerry S, Karamitsos TD, Prendergast
BD, Banning AP, Neubauer S, Myerson SG. A prospective, double-blind, randomized
controlled trial of the angiotensin-converting enzyme inhibitor Ramipril In
Aortic Stenosis (RIAS trial). Eur Heart J Cardiovasc Imaging. 2015
Aug;16(8):834-41. doi: 10.1093/ehjci/jev043. Epub 2015 Mar 21. PubMed PMID:
25796267; PubMed Central PMCID: PMC4505792.


19: Szpot P, Buszewicz G. Determination of ramipril in human plasma and its
fragmentation by UPLC-Q-TOF-MS with positive electrospray ionization. Acta Pharm.
2015 Jun;65(2):159-69. doi: 10.1515/acph-2015-0018. PubMed PMID: 26011932.


20: Kaur P, Muthuraman A, Kaur J. Ameliorative potential of
angiotensin-converting enzyme inhibitor (ramipril) on chronic constriction injury
of sciatic nerve induced neuropathic pain in mice. J Renin Angiotensin
Aldosterone Syst. 2015 Mar;16(1):103-12. doi: 10.1177/1470320314556171. Epub 2014
Dec 8. PubMed PMID: 25487978.