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Ramipril

Basic information Description References Safety Supplier Related

Ramipril Basic information

Product Name:
Ramipril
Synonyms:
  • 2-[[1-(2-ethoxycarbonyl-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrol-1-yl)-1-oxopropan-2-yl]amino]-4-phenylbutanoic acid
  • (2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
  • (2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]aMino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
  • RaMipril(Altace)
  • (2S,3aS,6aS)-
  • RaMipril API
  • Ranipril
  • (2s-(1(r*(r*)),2-alpha,3a-beta,6a-beta))-henylpropyl)amino)-1-oxopropyl
CAS:
87333-19-5
MF:
C23H32N2O5
MW:
416.51
EINECS:
642-904-3
Product Categories:
  • Ramipril
  • Angiotensin
  • Aromatics
  • Heterocycles
  • API
  • Cardiovascular & Blood System Agents
  • Active Pharmaceutical Ingredients
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
87333-19-5.mol
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Ramipril Chemical Properties

Melting point:
106-108°C
alpha 
D24 +33.2° (c = 1 in 0.1N ethanolic HCl)
Boiling point:
616.2±55.0 °C(Predicted)
Density 
1.200±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: ~18mg/mL
pka
pKa 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
CAS DataBase Reference
87333-19-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/38
Safety Statements 
26-37/39
WGK Germany 
2
RTECS 
GY5879600
HS Code 
2933995300
Hazardous Substances Data
87333-19-5(Hazardous Substances Data)
Toxicity
LD50 (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

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Ramipril Usage And Synthesis

Description

Ramipril (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.

References

https://en.wikipedia.org/wiki/Ramipril
https://www.drugbank.ca/drugs/DB00178

Description

Ramipril, 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 Properties

White Solid

Originator

Hoechst AG (W. Germany)

Uses

An antihypertensive. An angiotensin converting enzyme (ACE) inhibitor, converted to active, diacid metabolite

Uses

cardiotonic

Uses

An inhibitor of the angiotensin- coverting enzyme (ACE)

Uses

Angiotensin-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]

Definition

ChEBI: 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 name

Altace (King);Triatec.

General Description

Ramipril, (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 Actions

Angiotensin converting enzyme (ACE) inhibitor.

Veterinary Drugs and Treatments

Ramipril 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.

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