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MedKoo Cat#: 461149 | Name: Ramiprilat
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Description:

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

Ramiprilat is a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity.

Chemical Structure

Ramiprilat
Ramiprilat
CAS#87269-97-4

Theoretical Analysis

MedKoo Cat#: 461149

Name: Ramiprilat

CAS#: 87269-97-4

Chemical Formula: C21H28N2O5

Exact Mass: 388.1998

Molecular Weight: 388.46

Elemental Analysis: C, 64.93; H, 7.27; N, 7.21; O, 20.59

Price and Availability

Size Price Availability Quantity
5mg USD 500.00
10mg USD 800.00
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Related CAS #
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Synonym
Ramiprilat; HOE 498 diacid; HOE498 diacid, HOE-498 diacid, Ramipril diacid
IUPAC/Chemical Name
(2S,3aS,6aS)-1-(((S)-1-carboxy-3-phenylpropyl)-L-alanyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid
InChi Key
KEDYTOTWMPBSLG-HILJTLORSA-N
InChi Code
InChI=1S/C21H28N2O5/c1-13(22-16(20(25)26)11-10-14-6-3-2-4-7-14)19(24)23-17-9-5-8-15(17)12-18(23)21(27)28/h2-4,6-7,13,15-18,22H,5,8-12H2,1H3,(H,25,26)(H,27,28)/t13-,15-,16-,17-,18-/m0/s1
SMILES Code
O=C([C@@H]1C[C@@](CCC2)([H])[C@@]2([H])N1C([C@@H](N[C@H](C(O)=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 DMSO
Shelf Life
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ramiprilat functions as an angiotensin-converting enzyme inhibitor to suppress the conversion of angiotensin I to angiotensin II and the degradation of bradykinin. Ramiprilat is reported to interfere with the targeting of B2 kinin receptors to endothelial cell membranes. Additionally, ramiprilat has been reported to inhibit matrix metalloproteinase-3 and -9 activity in isolated Crohn’s disease fistulas.
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 388.46 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.
1: Trobec KČ, Grabnar I, Trontelj J, Lainščak M, Kos MK. Population pharmacokinetics of ramipril in patients with chronic heart failure: A real- world longitudinal study. Acta Pharm. 2024 May 30;74(2):315-328. doi: 10.2478/acph-2024-0018. PMID: 38815200. 2: Nandi S, Swain R, Habibullah S, Sahoo RN, Nayak AK, Mallick S. Lipid-Gelucire based rectal delivery of ramipril prodrug exhibits significant lowering of intra-ocular pressure in normotensive rabbit: sustained structural relaxation release kinetics and IVIVC. Pharm Dev Technol. 2024 Jun;29(5):468-476. doi: 10.1080/10837450.2024.2345807. Epub 2024 May 2. PMID: 38662798. 3: Dziadosz M, Rosenberger W, Klintschar M, Teske J. The analysis of ramipril/ramiprilat concentration in human serum with liquid chromatography- tandem mass spectrometry - interpretation of high concentrations for the purposes of forensic toxicology. Forensic Sci Med Pathol. 2024 Mar;20(1):100-105. doi: 10.1007/s12024-023-00621-6. Epub 2023 Apr 15. PMID: 37060536; PMCID: PMC10944385. 4: Jacobs CM, Kunz M, Mahfoud F, Wagmann L, Meyer MR. Closing the gap - development of an analytical methodology using volumetric absorptive microsampling of finger prick blood followed by LC-HRMS/MS for adherence monitoring of antihypertensive drugs. Anal Bioanal Chem. 2023 Jan;415(1):167-177. doi: 10.1007/s00216-022-04394-9. Epub 2022 Nov 1. PMID: 36318313; PMCID: PMC9816235. 5: Voronova A, Pagneux Q, Decoin R, Woitrain E, Butruille L, Barras A, Foulon C, Lecoeur M, Jaramillo D, Rumipamba J, Melinte S, Abderrahmani A, Montaigne D, Boukherroub R, Szunerits S. Heat-based transdermal delivery of a ramipril loaded cream for treating hypertension. Nanoscale. 2022 Sep 2;14(34):12247-12256. doi: 10.1039/d2nr02295h. PMID: 36000238. 6: Avataneo V, Fanelli E, De Nicolò A, Rabbia F, Palermiti A, Pappaccogli M, Cusato J, De Rosa FG, D'Avolio A, Veglio F. A Non-Invasive Method for Detection of Antihypertensive Drugs in Biological Fluids: The Salivary Therapeutic Drug Monitoring. Front Pharmacol. 2022 Jan 5;12:755184. doi: 10.3389/fphar.2021.755184. PMID: 35069191; PMCID: PMC8766966. 7: Regulska K, Musiał J, Stanisz BJ. Solid-State Stability Profiling of Ramipril to Optimize Its Quality Efficiency and Safety. Pharmaceutics. 2021 Oct 2;13(10):1600. doi: 10.3390/pharmaceutics13101600. PMID: 34683893; PMCID: PMC8538641. 8: Kably B, Billaud EM, Derobertmasure A, Blanchard A, Boutouyrie P, Azizi M. Urine N-acetyl-Ser-Asp-Lys-Pro measurement as a versatile biomarker to assess adherence to angiotensin-converting enzyme inhibitors. J Hypertens. 2022 Feb 1;40(2):348-355. doi: 10.1097/HJH.0000000000003018. PMID: 34508023. 9: Sus J, Huguet J, Bosak J, Setnik B, Hauser T, Sicard E. The bioequivalence of fixed-dose combination tablets of bisoprolol and ramipril and its drug-drug interaction potential. Clin Transl Sci. 2022 Jan;15(1):158-171. doi: 10.1111/cts.13128. Epub 2021 Sep 8. PMID: 34498388; PMCID: PMC8742637. 10: Kiew LV, Chang CY, Huang SY, Wang PW, Heh CH, Liu CT, Cheng CH, Lu YX, Chen YC, Huang YX, Chang SY, Tsai HY, Kung YA, Huang PN, Hsu MH, Leo BF, Foo YY, Su CH, Hsu KC, Huang PH, Ng CJ, Kamarulzaman A, Yuan CJ, Shieh DB, Shih SR, Chung LY, Chang CC. Development of flexible electrochemical impedance spectroscopy- based biosensing platform for rapid screening of SARS-CoV-2 inhibitors. Biosens Bioelectron. 2021 Jul 1;183:113213. doi: 10.1016/j.bios.2021.113213. Epub 2021 Apr 3. PMID: 33857754; PMCID: PMC8018905. 11: Hermann R, Gundlach K, Seiler D. Mechanistic Considerations About an Unexpected Ramipril Drug-Drug Interaction in the Development of a Triple Fixed- Dose Combination Product Containing Ramipril, Amlodipine, and Atorvastatin. Clin Pharmacol Drug Dev. 2021 Nov;10(11):1307-1315. doi: 10.1002/cpdd.930. Epub 2021 Mar 27. PMID: 33773093. 12: Chernonosov A. The Use of Dried Blood Spots for the Quantification of Antihypertensive Drugs. Int J Anal Chem. 2018 Aug 1;2018:3235072. doi: 10.1155/2018/3235072. PMID: 30154849; PMCID: PMC6093062. 13: Dubey R, Ghosh M. Simultaneous Determination and Pharmacokinetic Study of Losartan, Losartan Carboxylic Acid, Ramipril, Ramiprilat, and Hydrochlorothiazide in Rat Plasma by a Liquid Chromatography/Tandem Mass Spectrometry Method. Sci Pharm. 2014 Nov 30;83(1):107-24. doi: 10.3797/scipharm.1410-15. PMID: 26839805; PMCID: PMC4729183. 14: 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. PMID: 26639833. 15: Khan U, Nicell J. Human Health Relevance of Pharmaceutically Active Compounds in Drinking Water. AAPS J. 2015 May;17(3):558-85. doi: 10.1208/s12248-015-9729-5. Epub 2015 Mar 5. PMID: 25739816; PMCID: PMC4406958. 16: Lavorini F, Chellini E, Innocenti M, Campi G, Egan CG, Mogavero S, Fontana GA. A crossover randomized comparative study of zofenopril and ramipril on cough reflex and airway inflammation in healthy volunteers. Cough. 2014 Dec 24;10(1):7. doi: 10.1186/s12997-014-0007-5. PMID: 25632296; PMCID: PMC4308941. 17: Fukami K, Yamagishi S, Coughlan MT, Harcourt BE, Kantharidis P, Thallas- Bonke V, Okuda S, Cooper ME, Forbes JM. Ramipril inhibits AGE-RAGE-induced matrix metalloproteinase-2 activation in experimental diabetic nephropathy. Diabetol Metab Syndr. 2014 Aug 13;6(1):86. doi: 10.1186/1758-5996-6-86. PMID: 25143788; PMCID: PMC4138378. 18: Tian S, Ge X, Wu K, Yang H, Liu Y. Ramipril protects the endothelium from high glucose-induced dysfunction through CaMKKβ/AMPK and heme oxygenase-1 activation. J Pharmacol Exp Ther. 2014 Jul;350(1):5-13. doi: 10.1124/jpet.114.212928. Epub 2014 Apr 16. PMID: 24741076. 19: Cvan Trobec K, Trontelj J, Springer J, Lainscak M, Kerec Kos M. Liquid chromatography-tandem mass spectrometry method for simultaneous quantification of bisoprolol, ramiprilat, propranolol and midazolam in rat dried blood spots. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 May 1;958:29-35. doi: 10.1016/j.jchromb.2014.03.009. Epub 2014 Mar 15. PMID: 24686237. 20: Potier L, Waeckel L, Vincent MP, Chollet C, Gobeil F Jr, Marre M, Bruneval P, Richer C, Roussel R, Alhenc-Gelas F, Bouby N. Selective kinin receptor agonists as cardioprotective agents in myocardial ischemia and diabetes. J Pharmacol Exp Ther. 2013 Jul;346(1):23-30. doi: 10.1124/jpet.113.203927. Epub 2013 Apr 16. PMID: 23591995.