Ramiprilat
Grundinformationen
- CAS
87269-97-4- Standard-SMILES
C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21- InChIKey
KEDYTOTWMPBSLG-HILJTLORSA-N- Summenformel
- C21H28N2O5
- Durchschnittliche Molmasse
- 388,5 g/mol
- Monoisotopische Masse
- 388,199822
Überblick
Ramiprilat is a dipeptide that is the active metabolite of ramipril. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, a drug metabolite, a matrix metalloproteinase inhibitor, a cardioprotective agent and a bradykinin receptor B2 agonist. It is a dicarboxylic acid, an azabicycloalkane, a cyclopentapyrrole and a dipeptide. It is a conjugate acid of a ramiprilat(1-).
Namen und Bezeichner
- Bevorzugter Name
- Ramiprilat
- IUPAC
- (2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
- Englischer Name
- Ramiprilat
- Summenformel
- C21H28N2O5
- Molmasse
- 388.46
Namen und Synonyme
RamiprilatRamiprilate87269-97-4Ramipril DiacidRamiprilatum6N5U4QFC3GDTXSID401016165CHEBI:77363(2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[d]pyrrole-2-carboxylic acid(2S,3aS,6aS)-1-((2S)-2-(((2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta(d)pyrrole-2-carboxylic acidRefChem:57069DTXCID801474301
Weitere Namen anzeigen
Ramipril Impurity ERamipleyRAMIPRIL USPHOE 498 DiacidRAMIPRILAT HYDRATERamiprilat USP/EP/BP
(2S,3aS,6aS)-1-((2S)-2-(((1S)-1-carboxy-3-phenylpropyl)amino)propanoyl)-octahydrocyclopenta(b)pyrrole-2-carboxylic acidRamiprilat [INN]Ramipril EP Impurity EMFCD00865787Ramiprilat (Ramipril Diacid)(2S,3aS,6aS)-1-(((S)-1-carboxy-3-phenylpropyl)-L-alanyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acidRamipril EP Impurity E (Ramiprilat)(2S,3aS,6aS)-1-((S)-N-((S)-1-Carboxy-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 107 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 589
Physikochemische Eigenschaften
- Schmelzpunkt
- 139 · 139-141°C
- Siedepunkt
- 632.2 · 632.2±55.0 °C(Predicted)
- Dichte
- 1.273 · 1.273±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 2.2 · 2.20±0.10(Predicted)
- Farbe
- White to Pale Yellow
- Stabilität
- Hygroscopic
- InChIKey
- KEDYTOTWMPBSLG-HILJTLORSA-N
- SMILES
- N1(C(=O)[C@@H](N[C@H](C(O)=O)CCC2=CC=CC=C2)C)[C@H](C(O)=O)C[C@]2([H])CCC[C@]12[H]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- risk_code
- 36/38
- hazard_code
- Xi
- safety_code
- 26-37/39
Chemie und Industrie
Pharmakologische Informationen
FDA Pharmacological Classification
6N5U4QFC3G
RAMIPRILAT
Established Pharmacologic Class [EPC] - Angiotensin Converting Enzyme Inhibitor
Mechanisms of Action [MoA] - Angiotensin-converting Enzyme Inhibitors
Ramiprilat is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of ramiprilat is as an Angiotensin-converting Enzyme Inhibitor.
MeSH Pharmacological Classification
A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysRamipril Action Pathway
Anwendungen
BeschreibungRamiprilat 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.
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