Ramiprilat

Base Information

• Chemical Name: Ramiprilat
• CAS No.: 87269-97-4
• Molecular Formula: C21H28N2O5
• Molecular Weight: 388.464
• Hs Code.: 3004909090
• European Community (EC) Number: 807-772-5
• UNII: 6N5U4QFC3G
• DSSTox Substance ID: DTXSID401016165
• Nikkaji Number: J33.166J
• Wikidata: Q27088514
• NCI Thesaurus Code: C72911
• RXCUI: 1546377
• Pharos Ligand ID: 7SVRRGP55FHU
• Metabolomics Workbench ID: 154870
• ChEMBL ID: CHEMBL1201365
• Mol file: 87269-97-4.mol

Synonyms:ramiprilat

Chemical Property of Ramiprilat

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 7.47E-17mmHg at 25°C
• Melting Point: 139-141°C
• Refractive Index: 1.583
• Boiling Point: 632.2 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 336.2 °C
• PSA: 106.94000
• Density: 1.273 g/cm³
• LogP: 2.23350
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 388.19982200
• Heavy Atom Count: 28
• Complexity: 589

Purity/Quality:

99% ^*data from raw suppliers

Ramiprilat| ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N1C2CCCC2CC1C(=O)O)NC(CCC3=CC=CC=C3)C(=O)O
• Isomeric SMILES: C[C@@H](C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(=O)O)N[C@@H](CCC3=CC=CC=C3)C(=O)O
• Description: Ramiprilat is the active metabolite of ramipril and functions as an angiotensin-converting enzyme inhibitor (pKi = 9.08 in human heart) to suppress the conversion of angiotensin I to angiotensin II and the degradation of bradykinin, thereby preventing vasoconstriction. Furthermore, ramiprilat is reported to interfere with the targeting of B2 kinin receptors to endothelial cell membranes further preventing bradykinin signaling. In addition to its cardioprotective effects in both animal models and clinical studies, ramiprilat has been reported to inhibit matrix metalloproteinase-3 and -9 activity in isolated Crohn’s disease fistulas.
• Uses: Ramiprilat (Ramipril EP Impurity E) is a metabolite of Ramipril (R111000), and acts as an ACE inhibitor (1). Reduces the need for dialysis among patients previously on angiotensin-converting-enzyme inhibitors (2). Ramipril is used in stroke prevention. (3)

Technology Process of Ramiprilat

There total 2 articles about Ramiprilat which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Ramipril (87333-19-5,104195-90-6,1246253-05-3) → ramiprilate (87269-97-4)

Guidance literature:

at 37 ℃; esterase from various rat tissue homogenates or plasma;

Reference yield:

Ramipril (87333-19-5,104195-90-6,1246253-05-3) → ramiprilate (87269-97-4) + ramipril diketopiperazine

Guidance literature:

With water; In methanol; at 80 ℃; for 30h;

DOI:10.4067/S0717-97072010000400008

upstream raw materials:

Ramipril

Refernces

• 1、 Samy Mostafa, Noha,AbdElHamid, Ghada,Elsayed Zaazaa, Hala,Mohamed Amer, Sawsan. "Two validated stability-indicating chromatographic methods for the separation of two anti-hypertensive combinations in the presence of their degradation products or impurities". . p. 2427 - 2439. Retrieved 2019/07/16.
• 2、 Van Antwerpen, Pierre,Legssyer, Ilham,Zouaoui Boudjeltia, Karim,Babar, Sajida,Moreau, Patrick,Moguilevsky, Nicole,Vanhaeverbeek, Michel,Ducobu, Jean,Neve, Jean. "Captopril inhibits the oxidative modification of apolipoprotein B-100 caused by myeloperoxydase in a comparative in vitro assay of angiotensin converting enzyme inhibitors". . p. 31 - 36. Retrieved 2007/10/03.