87333-19-5 Usage
Description
Different sources of media describe the Description of 87333-19-5 differently. You can refer to the following data:
1. 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.
2. 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.
References
https://en.wikipedia.org/wiki/Ramipril
https://www.drugbank.ca/drugs/DB00178
Chemical Properties
White Solid
Uses
Different sources of media describe the Uses of 87333-19-5 differently. You can refer to the following data:
1. An antihypertensive. An angiotensin converting enzyme (ACE) inhibitor, converted to active, diacid metabolite
2. An inhibitor of the angiotensin- coverting enzyme (ACE)
3. 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.
Clinical Use
Angiotensin-converting enzyme inhibitor:
Hypertension
Secondary prevention of myocardial infarction (MI),
stroke or cardiovascular death
Heart failure
Diabetic nephropathy
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.
Drug interactions
Potentially 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
Metabolism
Ramipril 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.
Check Digit Verification of cas no
The CAS Registry Mumber 87333-19-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,3,3 and 3 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 87333-19:
(7*8)+(6*7)+(5*3)+(4*3)+(3*3)+(2*1)+(1*9)=145
145 % 10 = 5
So 87333-19-5 is a valid CAS Registry Number.
InChI:InChI=1/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1
87333-19-5Relevant articles and documents
Drug intermediate in ACE- inhibitor synthesis and application thereof
-
Paragraph 0014, (2020/03/17)
Compound (I) of Formula, wherein R1 is aryl or alkyl ;R2 represents alkyl ;R3 represents alkyl or aralkyl, is a valuable pharmacological intermediate, which may be prepared by reacting a compound of Formula (IV) above (with thionyl chloride as defined above R1 in particular by reacting a compound of Formula R2 with thionyl chloride), especially for use in the preparation, inhibitor, such as for example for (VI) eperindopril or ramipril 2. ((I). The compound X of Formula . R3 is as defined (I) above). wherein (II) and (are defined above ACE. R1 and R2 wherein R is. a compound, of formula,).
A METHOD FOR PREPARING RAMIPRIL
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Paragraph 0042, (2015/04/15)
Enantio-specific synthesis of optically pure (2S)-acetylamino-3-(2-oxo-cyclopentyl)- propionic acid (I) comprising converting enantiomeric mixture of (1 -4C alkyl)-2- acetylamino-3-(2-oxocyclopentyl) propionoate (II) (+ and -) under the influence of an Alkaline serine endopeptidase is disclosed. The invention further describes use of optically pure (2S)-acetylamino-3-(2-oxocyclopentyl)-propionic acid (I) formed by the process of present invention, in the preparation of Ramipril.
PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE
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, (2015/01/07)
A process for the production of amides of N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine is described. The process can be used for the production of key intermediates and finally the ACE inhibitors such as Ramipril, Enalapril, Quinapril, Trandolapril, Delapril and Moexipril starting from N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine by the reaction with the appropriate amines.
