Ramipril

Ramipril Basic information
Description References
Product Name:Ramipril
Synonyms:Ramioril;(2S,3AS,6AS)-1-((S)-2-((S)-1-ETHOXY-1-OXO-4-PHENYLBUTAN-2-YLAMINO)PROPANOYL)-OCTAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID;Triatec;Trimce;vesdil;(1S,5S,7S)-8-[(2S)-2-[[(1S)-1-Ethoxycarbonyl-3-phenyl-propyl]amino]propanoyl]-8-azabicyclo[3.3.0]octane-7-carboxylic acid;Cyclopenta(b)pyrrole-2-carboxylic acid, octahydro-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl) amino)-1-oxopropyl), (2S-(1(R*(R*)),2-alpha,3a-beta,6a-beta));4-[2-(1-Ethoxycarbonyl-3-phenyl-propyl)aminopropanoyl]-4-azabicyclo[3.3.0]octane-3-carboxylic acid
CAS:87333-19-5
MF:C23H32N2O5
MW:416.51
EINECS:642-904-3
Product Categories:Ramipril;Angiotensin;Cardiovascular & Blood System Agents;API;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Active Pharmaceutical Ingredients
Mol File:87333-19-5.mol
Ramipril Structure
Ramipril Chemical Properties
Melting point 106-108°C
Boiling point 616.2±55.0 °C(Predicted)
alpha D24 +33.2° (c = 1 in 0.1N ethanolic HCl)
density 1.200±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: ~18mg/mL
pkapKa 3.30±0.01(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain);5.75±0.00(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain)
form powder
color white
BCS Class1
CAS DataBase Reference87333-19-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/38
Safety Statements 26-37/39
WGK Germany 2
RTECS GY5879600
HS Code 2933995300
Hazardous Substances Data87333-19-5(Hazardous Substances Data)
ToxicityLD50 (14 day) in male, female mice, male, female rats (mg/kg): 1194, 1158, 687, 608 i.v.; 10933, 10048, >10000, >10000 orally (Donaubauer, Mayer)
MSDS Information
ProviderLanguage
Ramipril English
Ramipril Usage And Synthesis
DescriptionRamipril (brand name: Altace) is a kind of prodrug which is capable of inhibiting the angiotensin-converting enzyme (ACE) which converting angiotensin I to angiotensin II. It is metabolized to ramiprilat in the liver which exerts the effect of ACE inhibition. It is used for the treatment of hypertension, congestive heart failure and nephropathy. It can also be used for the prevention of heart attack, stroke and cardiovascular death. It can also be used for the treatment of kidney damage due to diabetes with protein-containing urine. Ramiprilat, is the competitive inhibitor of ATI for binding to ACE, further inhibiting the enzymatic proteolysis of ATI to ATII, alleviating the effect of ATII on blood pressure.
Referenceshttps://en.wikipedia.org/wiki/Ramipril
https://www.drugbank.ca/drugs/DB00178
DescriptionRamipril, a prodrug of ramiprilat, is a long-acting, tissue-specific and non-sulfhydryl ACE inhibitor useful in the treatment of mild to moderate hypertension. In animal studies ramipril exerted cardioprotective effects resembling those of bradykinin in cardiac reperfusion injuries. Ramipril is also reportedly useful in congestive heart failure.
Chemical PropertiesWhite Solid
OriginatorHoechst AG (W. Germany)
UsesAn inhibitor of the angiotensin- coverting enzyme (ACE)
Usescardiotonic
UsesAn antihypertensive. An angiotensin converting enzyme (ACE) inhibitor, converted to active, diacid metabolite
UsesAngiotensin-converting enzyme (ACE) removes the C-terminal dipeptide from angiotensin I to form angiotensin II, a powerful vasoconstrictor. ACE is a key regulator of the renin-angiotensin system and an important drug target for the treatment of hypertension, congestive heart failure, and heart attacks, and also in preventing renal and retinal complications in diabetes. Ramipril is a second generation ACE inhibitor (IC50 = 4 nM) that acts as a prodrug, which is hydrolyzed in vivo to the active metabolite ramiprilat. The antihypertensive and cardioprotective efficacy of ramipril has been demonstrated in large-scale noncomparative studies and clinical trials.[Cayman Chemical]
DefinitionChEBI: A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.
Brand nameAltace (King);Triatec.
General DescriptionRamipril, (2S, 3aS, 6aS)-1-[(S)-N-[(S)-1-carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]-pyrrole-2-carboxylic acid 1-ethyl ester (Altace), ishydrolyzed to ramiprilat, its active diacid form, faster thanenalapril is hydrolyzed to its active diacid form. Peak serumconcentrations from a single oral dose are achieved between1.5 and 3 hours. The ramiprilate formed completely suppresses ACE activity for up to 12 hours, with 80% inhibitionof the enzyme still observed after 24 hours.
Biochem/physiol ActionsAngiotensin converting enzyme (ACE) inhibitor.
Clinical UseAngiotensin-converting enzyme inhibitor:
Hypertension
Secondary prevention of myocardial infarction (MI), stroke or cardiovascular death
Heart failure
Diabetic nephropathy



Veterinary Drugs and TreatmentsRamipril is a long-acting angiotensin converting enzyme (ACE) inhibitor that may be useful in treating heart failure or hypertension in dogs or cats. It is an approved product in the UK for treating heart failure in dogs. In cats, ramipril has been used for treating arterial hypertension. A recent study (MacDonald, Kittleson et al. 2006) did not show any significant benefit using ramipril in treating Maine Coon cats with hypertrophic cardiomyopathy without heart failure.
Like other ACE inhibitors, it may potentially be useful as adjunctive treatment in chronic renal failure and protein losing nephropathies. In dogs with moderate renal impairment (such as might be found with CHF), there is apparently no need to adjust ramipril dosage.
Drug interactionsPotentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs.
Antihypertensives: increased risk of hyperkalaemia, hypotension and renal failure with ARB’S and aliskiren.
Bee venom extract: possible severe anaphylactoid reactions when used together.
Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity.
Cytotoxics: increased risk of angioedema with everolimus.
Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics.
ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect.
Gold: flushing and hypotension with sodium aurothiomalate.
Lithium: reduced excretion (possibility of enhanced lithium toxicity).
Potassium salts: increased risk of hyperkalaemia.
Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity



MetabolismRamipril is metabolised in the liver to its active metabolite, ramiprilat, and other inactive metabolites. It is excreted mainly in the urine, as ramiprilat, other metabolites, and some unchanged drug. About 40% of an oral dose appears in the faeces; this may represent both biliary excretion and unabsorbed drug.
storageStore at +4°C
Ramipril Diketopiperazine RAMIPRIL-D5 RAMIPRIL ANTIHYPERTENSIVE Intermediate Of Ramipril Ramipril EP ENDO, CIS-2-AZABICYCLO [3,3,0] OCTANE-3-CARBORYLIC ACID BENZYL ESTER HYDROCHLORIDE (FOR RAMIPRIL) Carbonyl iron powder RAMIPRIL IMPURITY B RAMIPRIL ACYL-B-D-GLUCURONIDE Ramipril Related Compound B RAMIPRIL RELATED COMPOUND B (20 MG) (RAMIPRIL ISOPROPYLESTER) RAMIPRIL IMPURITY C RAMIPRIL-D5 ACYL-B-D-GLUCURONIDE RAMIPRIL RELATED COMPOUND C (20 MG) (HEX-AHYDRORAMIPRIL HYDROCHLORIDE) 2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER RAMIPRIL-D3 RAMIPRIL IMPURITY D RAMIPRIL IMP. G (EP): TOLUENE

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