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Ramipril

CAS No.
87333-19-5
Chemical Name:
Ramipril
Synonyms
ALTACE;RaMipril API;(2s-(1(r*(r*)),2-alpha,3a-beta,6a-beta))-henylpropyl)amino)-1-oxopropyl;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;DELIX;vesdil;Trimce;RAMACE;Triatec;UNIPRIL
CBNumber:
CB0249104
Molecular Formula:
C23H32N2O5
Molecular Weight:
416.51
MDL Number:
MFCD00865775
MOL File:
87333-19-5.mol
MSDS File:
SDS
Last updated:2024-04-15 15:30:59

Ramipril 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
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
BCS Class 1
CAS DataBase Reference 87333-19-5(CAS DataBase Reference)
FDA UNII L35JN3I7SJ
NCI Drug Dictionary Altace
ATC code C09AA05

Pharmacokinetic data

Protein binding 56 (as ramiprilat)
Excreted unchanged in urine <2%
Volume of distribution 1.2(L/kg)
Biological half-life 13-17 / Increased (as ramiprilat)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Danger
Hazard statements  H360FD
Precautionary statements  P201-P202-P280-P308+P313-P405-P501
Hazard Codes  Xi
Risk Statements  36/38
Safety Statements  26-37/39
WGK Germany  2
RTECS  GY5879600
HS Code  2933995300
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)
NFPA 704
0
2 0

Ramipril price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1446 Ramipril Pharmaceutical Secondary Standard; Certified Reference Material 87333-19-5 1g $114 2024-03-01 Buy
Sigma-Aldrich BP751 Ramipril British Pharmacopoeia (BP) Reference Standard 87333-19-5 100MG $255 2024-03-01 Buy
Sigma-Aldrich 1598303 Ramipril United States Pharmacopeia (USP) Reference Standard 87333-19-5 125mg $436 2024-03-01 Buy
TCI Chemical R0219 Ramipril 87333-19-5 1G $122 2024-03-01 Buy
TCI Chemical R0219 Ramipril 87333-19-5 5G $301 2024-03-01 Buy
Product number Packaging Price Buy
PHR1446 1g $114 Buy
BP751 100MG $255 Buy
1598303 125mg $436 Buy
R0219 1G $122 Buy
R0219 5G $301 Buy

Ramipril Chemical Properties,Uses,Production

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 inhibitor of the angiotensin- coverting enzyme (ACE)

Uses

cardiotonic

Uses

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

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.

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.

storage

Store at +4°C

87269-88-3
87333-19-5
Synthesis of Ramipril from 2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER
Global( 422)Suppliers
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View Lastest Price from Ramipril manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ramipril pictures 2024-04-15 Ramipril
87333-19-5
US $32.00-1.30 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
Ramipril pictures 2024-03-16 Ramipril
87333-19-5
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Ramipril pictures 2023-11-01 Ramipril
87333-19-5
US $0.00-0.00 / kg 1kg 99.0% 20 tons Hangzhou ICH Biofarm Co., Ltd
  • Ramipril pictures
  • Ramipril
    87333-19-5
  • US $32.00-1.30 / KG
  • 99%
  • Henan Fengda Chemical Co., Ltd
  • Ramipril pictures
  • Ramipril
    87333-19-5
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Ramipril pictures
  • Ramipril
    87333-19-5
  • US $0.00-0.00 / kg
  • 99.0%
  • Hangzhou ICH Biofarm Co., Ltd

Ramipril Spectrum

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 (2S,3aβ,6aβ)-1-[(S)-2-[[(S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2α-carboxylic acid Ramipril (125 mg) Tritace, [2S,3aS,6aS]-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid [2S-[1[R^<*>^ (R^<*>^)],2α,3αβ,6αβ]]-1-[2-[[1- (Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahy-drocyclopenta[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)- Ranipril UNIPRIL TRITACE PRAMACE RAMIPRIL RAMACE cyclopenta(b)pyrrole-2-carboxylicacid,octahydro-1-(2-((1-(ethoxycarbonyl)-3-p [2S,3AS,6AS]-1-[(2S)-2-[[(1S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL]AMINO]-1-OXOPROPYL]OCTAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID (2S,3AS,6AS)-1-[(S)-2-((S)-1-ETHOXYCARBONYL-3-PHENYL-PROPYLAMINO)-PROPIONYL]-OCTAHYDRO-CYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID (2s,3as,6as)-1((s)-n-((s)-1-carboxy-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid 1-ethyl ester RAMIPRIL, IMPURITY B(2S,3AS,6AS)-1-[(S)-2-[[(S)-1-[(METHYLETHOXY)CARBONYL]-3-PHENYLPROPYL]AMINO] PROPANOYL]OCTAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID(RAMIPRIL ISOPROPYL ESTER) EP STANDARD RAMIPRIL, USP STANDARD RAMIPRIL, EP STANDARD RAMIPRIL, RELATED COMPOUND A5-[[2-(AMINOETHYL)THIO]METHYL]-N,N-DIMETHYL-2-FURANMETHANINE HEMIFUMARATE SALT USP STANDARD RAMIPRIL, IMPURITY DETHYL(2S)-2-[(3S,5AS,8AS,9AS)-3-METHYL-1,4-DIOXODECAHYDRO-1H-CYCLOPENTA[E]PYRROLO[1,2A]PYRAZIN-2-YL]-4-PHENYLBUTANOATE EP STANDARD RAMIPRIL, IMPURITY C(2S,3AS,6AS)-1-[(S)-2-[[(S)-1-(ETHOXYCARBONYL)-3-CYCLOHEXYLPROPYL]AMINO]PROPANOYL]OCTAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID (HEXAHYDRORAMIPRIL) EP STANDARD RAMIPRIL, IMPURITY A(2S,3AS,6AS)-1-[(S)-2-[[(S)-1-(METHOXYCARBONYL)-3-PHENYLPROPYL]AMINO]PROPANOLY]OCTAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID (RAMIPRIL METHYLESTER) EP STANDARD CARDACE HOE-498 DELIX Raimipril RamiprilC23H32N205 HOE-498, Altace, Cardace, Delix, Pramace, Ramace, Unipril Cyclopentabpyrrole-2-carboxylic acid, 1-(2S)-2-(1S)-1-(ethoxycarbonyl)-3-phenylpropylamino-1-oxopropyloctahydro-, (2S,3aS,6aS)- (2s,3as,6as)-1-[(s)-2-[[(s)-1-(ethoxycarbonyl)-3phenylpropyl]amino]propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid cyclopenta(b)pyrrole-2-carboxylic acid, octahydro-1-(2-((1-(ethoxycarbonyl)-3-phoeramipril (2S,3aS,6aS)-1-((S)-2-((S)-1-ethoxy-1-oxo-4- CAS 87333-19-5 Ramipril Powder 2S,3aS,6aS)-1((S)-N-((S)-1-Carboxy-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid 1-ethyl ester Ramipril CRS Calcipotriol impurity MC-1080 Carasel Ramipril USP/EP/BP Ramipril (1.0 mg/mL in Methanol) Ramipri Ramipril (HOE-498) RamiprilQ: What is Ramipril Q: What is the CAS Number of Ramipril Q: What is the storage condition of Ramipril Q: What are the applications of Ramipril Ramipril (1598303) (2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid RaMipril API (2s-(1(r*(r*)),2-alpha,3a-beta,6a-beta))-henylpropyl)amino)-1-oxopropyl ALTACE 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