Identification

Name
Ramipril
Accession Number
DB00178
Description

Ramipril is a prodrug belonging to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to ramiprilat in the liver and, to a lesser extent, kidneys. Ramiprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Ramipril may be used in the treatment of hypertension, congestive heart failure, nephropathy, and to reduce the rate of death, myocardial infarction and stroke in individuals at high risk of cardiovascular events.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 416.5106
Monoisotopic: 416.231122144
Chemical Formula
C23H32N2O5
Synonyms
  • (2S-(1(R*(R*)),2alpha,3abeta,6abeta))-1-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid
  • Ramipril
  • Ramiprilum
External IDs
  • C09AA05
  • HOE 498

Pharmacology

Indication

For the management of mild to severe hypertension. May be used to reduce cardiovascular mortality following myocardial infarction in hemodynamically stable individuals who develop clinical signs of congestive heart failure within a few days following myocardial infarction. Label To reduce the rate of death, myocardial infarction and stroke in individuals at high risk of cardiovascular events. May be used to slow the progression of renal disease in individuals with hypertension, diabetes mellitus and microalubinuria or overt nephropathy. 5

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Ramipril is an ACE inhibitor similar to benazepril, fosinopril and quinapril. 5 It is an inactive prodrug that is converted to ramiprilat in the liver, the main site of activation, and kidneys. Ramiprilat confers blood pressure lowing effects by antagonizing the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may sustain the effects of ramiprilat by causing increased vasodilation and decreased blood pressure.

Mechanism of action

Ramipril inhibits the RAAS system by binding to and inhibiting ACE thereby preventing the conversion of angiotensin I to angiotensin II. 5 As plasma levels of angiotensin II fall, less activation of the G-protein coupled receptors angiotensin receptor I (AT1R) and angiotensin receptor II (AT2R) occurs.

AT1R mediates vasoconstriction, inflammation, fibrosis, and oxidative stress through a variety of signaling pathways. 5 These include Gq coupling to the inositol triphosphate pathway, activation of phospholipases C, A2, and D which contribute to eicosanoid production, activation of Ca2+-dependent and MAP kinases, Gi and G12/13, and eventual activation of the Jak/STAT pathway leading to cell growth and production of extracellular matrix components. AT1R activation also leads to increased activity of membrane-bound NADH/NADPH oxidase which contributes to production of reactive oxygen species. Decreased activation of this receptor mediates the renoprotective, antihypertensive, and cardioprotective effects of ramipril by reducing inflammation and vasoconstriction.

AT2R acts in opposition to the effects of AT1R by activating phosphotyrosine phosphatases which inhibit MAP kinases, inhibiting Ca2+ channel opening, and stimulating cGMP and nitric oxide production leading to vasodilation. 5 These counteracting effects are shared by the Mas receptor which is activated by Ang(1-7), a subtype of angiotensin produced by plasma esterases from AngI or by ACE2 from AngII produced through a secondary pathway by tonin and cathepsin G. Ang(1-7) also activates AT2R although the bulk of its effect is mediated by MasR.

ACE is also responsible for the breakdown of bradykinin. 5 The resulting buildup of bradykinin due to ACE inhibition is thought to mediate the characteristic dry-cough as a side effect of ACE inhibitor medications.

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Humans
UB1 bradykinin receptorNot AvailableHumans
Absorption

The extent of absorption is at least 50-60%.Label. Food decreases the rate of absorption from the GI tract without affecting the extent of absorption. The absolute bioavailabilities of ramipril and ramiprilat were 28% and 44%, respectively, when oral administration was compared to intravenous administration. The serum concentration of ramiprilat was unchanged when capsules were opened and the contents dissolved in water, dissolved in apple juice, or suspended in apple sauce.

Volume of distribution
Not Available
Protein binding

Protein binding of ramipril is about 73% and that of ramiprilat about 56%.Label Protein binding is independent of concentration over the range of 0.1μg/mL-10μg/mL

Metabolism

Hepatic metabolism accounts for 75% of total ramipril metabolism.Label 25% of hepatic metabolism produces the active metabolite ramiprilat via liver esterase enzymes. 100% of renal metabolism converts ramipril to ramiprilat. Other metabolites, diketopiperazine ester, the diketopiperazine acid, and the glucuronides of ramipril and ramiprilat, are inactive.

Hover over products below to view reaction partners

Route of elimination

60% of the parent drug and its metabolites are eliminated in the urine with the remaining 40% eliminated in the feces.Label The drug eliminated in the feces represents both absorbed drug and drug eliminated through biliary excretion although the proportion of these has not been determined. Less than 2% of drug is eliminated in the urine unchanged.

Half-life

Plasma concentrations of ramiprilat decline in a triphasic manner.Label Initial rapid decline represents distribution into tissues and has a half life of 2-4 hours. The half life of the apparent elimination phase is 9-18 hours, which is thought to represent clearance of free drug. The half-life of the terminal elimination phase is > 50 hours and thought to represent clearance of drug bound to ACE due to its slow dissociation. The half life of ramiprilat after multiple daily doses (MDDs) is dose-dependent, ranging from 13-17 hours with 5-10 mg MDDs to 27-36 hours for 2.5 mg MDDs.

Clearance

The renal clearance of ramipril and ramiprilat was reported to be 7.2 and 77.4 mL/min/1.73m2. 4 The mean renal clearance of ramipril and ramiprilat is reported to be 10.7 and 126.8 mL/min in healthy elderly patients with normal renal function, additionally the Cmax of ramiprilat is approximately 20% higher in this population. While the pharmacokinetics of ramipril appear unaffected by reduced renal function, the plasma concentration and half-life of ramiprilat are increased. In patient's with hepatic failure the concentration of ramipril is initially increased while the tmax of ramiprilat is prolonged due to a reduced ability to metabolize the drug. However, steady state concentrations of ramiprilat are the same in hepatic failure as in healthy patients.

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Symptoms of overdose may include excessive peripheral vasodilation (with marked hypotension and shock), bradycardia, electrolyte disturbances, and renal failure. Cases of ACE inhibitor induced hepatotoxicity have been reported in humans and presented as acute jaundice and elevated liver enzymes.3 Removal of the ACE inhbitor resulted in a decline in liver enzymes and re-challenge produced a subsequent increase.

There were no observed tumerogenic effects at chronic doses up to 500mg/kg/day to rats for 24 months or at doses up to 1000mg/kg/day to mice for 18 months. For both species doses were administered by gavage and equivalent to 200 time the maximum recommended human exposure based on body surface area.

No mutagenic activity was detected in the Ames test in bacteria, the micronucleus test in mice, unscheduled DNA synthesis in a human cell line, or a forward gene-mutation assay in a Chinese hamster ovary cell line. Several metabolites of ramipril also produced negative results in the Ames test.

No effects on fertility were seen in rats at doses up to 500mg/kg/day. No teratogenicity was observed in rats and cynomolgus monkeys at doses 400 times the maximum recommended human exposure nor in rabbites at 2 times the maximum recommended human exposure.

LD50 10 g/kg (rat).MSDS LD50 10.5 g/kg (mouse).MSDS LD50 1 g/kg (dog).MSDS

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Ramipril Action PathwayDrug action
Ramipril Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Angiotensin-converting enzyme---(A;A) / (G;G)A Allele, homozygote / G Allele, homozygoteEffect Directly StudiedPatients with this genotype have a shorter time to lowering of blood pressure with ramiprilDetails

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololRamipril may increase the hypotensive activities of Acebutolol.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Ramipril.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Ramipril.
Acetylsalicylic acidThe therapeutic efficacy of Ramipril can be decreased when used in combination with Acetylsalicylic acid.
Agrostis gigantea pollenThe risk or severity of adverse effects can be increased when Ramipril is combined with Agrostis gigantea pollen.
Agrostis stolonifera pollenThe risk or severity of adverse effects can be increased when Ramipril is combined with Agrostis stolonifera pollen.
AlclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Alclofenac is combined with Ramipril.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Ramipril.
AlfentanilAlfentanil may decrease the antihypertensive activities of Ramipril.
AlfuzosinAlfuzosin may increase the hypotensive activities of Ramipril.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
  • Take with or without food. The absorption is unaffected by food.

Products

Active Moieties
NameKindUNIICASInChI Key
Ramiprilatprodrug6N5U4QFC3G87269-97-4KEDYTOTWMPBSLG-HILJTLORSA-N
Product Images
International/Other Brands
Acovil (Sanofi-Aventis (Spain)) / Carasel (Almirall (Spain)) / Cardace (Sanofi-Aventis (Finland), Aventis (India), Aventis (Indonesia)) / Delix (Aventis (Germany, Turkey), ) / Hypren (AstraZeneca (Austria)) / Lostapres (Temis (Argentina)) / Pramace (Astra (Ireland), AstraZeneca (Sweden)) / Quark (Polifarma (Italy)) / Triatec (Sanofi-Aventis (Brazil, Chili, Denmark, France, Greece, Indonesia, Italy,Norway, Portugal, Sweden, Switzerland)) / Tritace (Sanofi-Aventis (Argentina, Australia, Austria, Belgium, Czech Republic, Hong Kong, Hungary, Ireland, Israel, Malaysia, Mexico, Netherlands, Poland, Singapor, Thailand, United Kingdom), Aventis (New Zealand, Philippines, South Africa)) / Vesdil (AstraZeneca (Germany), Promed (Germany))
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act RamiprilCapsuleOralActavis Pharma Company2007-10-022019-08-13Canada flag
Act RamiprilCapsuleOralActavis Pharma Company2007-10-022019-08-13Canada flag
Act RamiprilCapsuleOralActavis Pharma Company2007-10-022019-08-13Canada flag
Act RamiprilCapsuleOralActavis Pharma Company2007-10-022019-08-13Canada flag
AltaceCapsule10 mg/1OralPfizer Laboratories Div Pfizer Inc1991-01-28Not applicableUS flag
AltaceCapsule2.5 mgOralValeant Canada Lp Valeant Canada S.E.C.1997-04-21Not applicableCanada flag
AltaceTablet5 mgOralValeant Canada Lp Valeant Canada S.E.C.Not applicableNot applicableCanada flag
AltaceCapsule1.25 mg/1OralPhysicians Total Care, Inc.2007-01-092012-06-30US flag
AltaceTablet2.5 mg/1OralKing Pharmaceuticals, Inc.2007-02-272008-10-08US flag
AltaceCapsule1.25 mg/1OralPfizer Laboratories Div Pfizer Inc1991-01-28Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ach-ramiprilCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-ramiprilCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-ramiprilCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-ramiprilCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ach-ramiprilCapsuleOralAccord Healthcare IncNot applicableNot applicableCanada flag
Ag-ramiprilCapsuleOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-ramiprilCapsuleOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-ramiprilCapsuleOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-ramiprilCapsuleOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-ramiprilCapsuleOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Altace HCTRamipril (10.0 mg) + Hydrochlorothiazide (25.0 mg)TabletOralValeant Canada Lp Valeant Canada S.E.C.2006-11-16Not applicableCanada flag
Altace HCTRamipril (5 mg) + Hydrochlorothiazide (12.5 mg)TabletOralValeant Canada Lp Valeant Canada S.E.C.2006-11-16Not applicableCanada flag
Altace HCTRamipril (5.0 mg) + Hydrochlorothiazide (25.0 mg)TabletOralValeant Canada Lp Valeant Canada S.E.C.2006-11-16Not applicableCanada flag
Altace HCTRamipril (2.5 mg) + Hydrochlorothiazide (12.5 mg)TabletOralValeant Canada Lp Valeant Canada S.E.C.2006-11-16Not applicableCanada flag
Altace HCTRamipril (10.0 mg) + Hydrochlorothiazide (12.5 mg)TabletOralValeant Canada Lp Valeant Canada S.E.C.2006-11-16Not applicableCanada flag
Altace Plus Felodipine 2.5mg + 2.5mgRamipril (2.5 mg) + Felodipine (2.5 mg)TabletOralSanofi Aventis2006-06-272012-10-10Canada flag
Altace Plus Felodipine 5mg + 5mgRamipril (5 mg) + Felodipine (5 mg)TabletOralSanofi Aventis2006-06-272012-10-15Canada flag
Apo-ramipril/hctzRamipril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ramipril/hctzRamipril (5 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex CorporationNot applicableNot applicableCanada flag
Apo-ramipril/hctzRamipril (10 mg) + Hydrochlorothiazide (25 mg)TabletOralApotex CorporationNot applicableNot applicableCanada flag

Categories

ATC Codes
C09BX03 — Ramipril, amlodipine and hydrochlorothiazideC10BX04 — Simvastatin, acetylsalicylic acid and ramiprilC10BX17 — Rosuvastatin and ramiprilC09BB07 — Ramipril and amlodipineC10BX06 — Atorvastatin, acetylsalicylic acid and ramiprilC09BB05 — Ramipril and felodipineC09BA05 — Ramipril and diureticsC09AA05 — Ramipril
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Alpha amino acid esters / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Fatty acid esters / Aralkylamines / Dicarboxylic acids and derivatives / Benzene and substituted derivatives / Tertiary carboxylic acid amides
show 9 more
Substituents
Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid monoester, ethyl ester, azabicycloalkane, dipeptide, cyclopentapyrrole (CHEBI:8774)

Chemical Identifiers

UNII
L35JN3I7SJ
CAS number
87333-19-5
InChI Key
HDACQVRGBOVJII-JBDAPHQKSA-N
InChI
InChI=1S/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
IUPAC Name
(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
SMILES
[H][[email protected]@]12CCC[[email protected]]1([H])N([[email protected]@H](C2)C(O)=O)C(=O)[[email protected]](C)N[[email protected]@H](CCC1=CC=CC=C1)C(=O)OCC

References

Synthesis Reference

Edward Wilson, Martin Beasley, "Stabilized ramipril compositions and methods of making." U.S. Patent US20060134213, issued June 22, 2006.

US20060134213
General References
  1. Cacciapuoti F, Capasso A, Mirra G, De Nicola A, Minicucci F, Gentile S: Prevention of left ventricular hypertrophy by ACE-inhibitor, ramipril in comparison with calcium-channel antagonist, felodipine. Int J Cardiol. 1998 Jan 31;63(2):175-8. [PubMed:9510492]
  2. Kleinert S: HOPE for cardiovascular disease prevention with ACE-inhibitor ramipril. Heart Outcomes Prevention Evaluation. Lancet. 1999 Sep 4;354(9181):841. [PubMed:10485736]
  3. Douros A, Kauffmann W, Bronder E, Klimpel A, Garbe E, Kreutz R: Ramipril-induced liver injury: case report and review of the literature. Am J Hypertens. 2013 Sep;26(9):1070-5. doi: 10.1093/ajh/hpt090. Epub 2013 Jun 8. [PubMed:23747952]
  4. Meisel S, Shamiss A, Rosenthal T: Clinical pharmacokinetics of ramipril. Clin Pharmacokinet. 1994 Jan;26(1):7-15. doi: 10.2165/00003088-199426010-00002. [PubMed:8137599]
  5. Hilal-Dandan R (2018). 26. In Goodman & Gilman's: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [ISBN:978-1-25-958473-2]
  6. FDA Approved Products: Altace (ramipril) oral capsules [Link]
Human Metabolome Database
HMDB0014324
KEGG Drug
D00421
PubChem Compound
5362129
PubChem Substance
46506390
ChemSpider
4514937
BindingDB
50084681
RxNav
35296
ChEBI
8774
ChEMBL
CHEMBL1168
ZINC
ZINC000003798757
Therapeutic Targets Database
DAP000581
PharmGKB
PA451223
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ramipril
AHFS Codes
  • 24:32.04 — Angiotensin-converting Enzyme Inhibitors
FDA label
Download (587 KB)
MSDS
Download (53.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentHigh Blood Pressure (Hypertension) / High Blood Pressure Variability1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedPreventionAdverse Effects / Coronary Artery Atherosclerosis / Insulin resistance syndrome1
4CompletedPreventionAlzheimer's Disease (AD) / High Blood Pressure (Hypertension)1
4CompletedPreventionCardiovascular Heart Disease1
4CompletedPreventionDiabetes / Proteinuria / Renin Angiotensin System1
4CompletedPreventionHigh Blood Pressure (Hypertension)1
4CompletedPreventionNephropathy, Diabetic1
4CompletedTreatmentAcute Heart Failure (AHF)1
4CompletedTreatmentAlbuminuria1

Pharmacoeconomics

Manufacturers
  • King pharmaceuticals inc
  • Actavis elizabeth llc
  • Apotex inc
  • Cipla ltd
  • Dr reddys laboratories ltd
  • Invagen pharmaceuticals inc
  • Lupin ltd
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
  • King Pharmaceuticals, Inc.
Packagers
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Arrow Pharm Malta Ltd.
  • A-S Medication Solutions LLC
  • Blu Pharmaceuticals LLC
  • Bryant Ranch Prepack
  • Camber Pharmaceuticals Inc.
  • Cardinal Health
  • Cipla Ltd.
  • Cobalt Pharmaceuticals Inc.
  • DAVA Pharmaceuticals
  • Dispensing Solutions
  • Doctor Reddys Laboratories Ltd.
  • Heartland Repack Services LLC
  • Hoechst Marion Roussel Canada Inc.
  • InvaGen Pharmaceuticals Inc.
  • Kaiser Foundation Hospital
  • King Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Lupin Pharmaceuticals Inc.
  • Mckesson Corp.
  • Monarch Pharmacy
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandoz
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Vangard Labs Inc.
Dosage Forms
FormRouteStrength
CapsuleOral15 mg
TabletOral1.25 mg/1
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral5 mg/1
Tablet2.5 MG
Tablet5 MG
Tablet, coated5 mg
Tablet10 MG
Tablet, extended releaseOral2.5 mg
Tablet, film coated10 mg
Tablet, film coated2.5 mg
Tablet, film coated5 mg
TabletOral10 MG
TabletOral2.5 MG
CapsuleOral1.25 mg
CapsuleOral
TabletOral
Capsule1.25 MG
Capsule2.5 MG
Capsule5 MG
Capsule10 mg
CapsuleOral10 mg
CapsuleOral2.5 mg
CapsuleOral5 mg
CapsuleOral1.25 mg/1
CapsuleOral10 mg/1
CapsuleOral10 mg/301
CapsuleOral2.5 mg/1
CapsuleOral5 mg/1
Capsule, gelatin coatedOral1.25 mg/1
Capsule, gelatin coatedOral10 mg/1
Capsule, gelatin coatedOral2.5 mg/1
Capsule, gelatin coatedOral5 mg/1
Powder1 kg/1kg
Tablet7.5 MG
TabletOral1.25 MG
Tablet1.25 MG
Tablet
TabletOral
Tablet, film coatedOral2.5 mg
Tablet, film coatedOral5 mg
Tablet, extended releaseOral5 mg
Tablet12.5 mg
TabletOral5 mg
Tablet25 mg
Prices
Unit descriptionCostUnit
Altace 10 mg capsule2.87USD capsule
Altace 2.5 mg capsule2.54USD capsule
Altace 5 mg capsule2.53USD capsule
Altace 10 mg tablet2.37USD tablet
Altace 1.25 mg capsule2.2USD capsule
Ramipril 10 mg capsule2.19USD capsule
Altace 5 mg tablet2.02USD tablet
Altace 2.5 mg tablet1.93USD tablet
Ramipril 5 mg capsule1.87USD capsule
Ramipril 2.5 mg capsule1.78USD capsule
Altace 1.25 mg tablet1.63USD tablet
Ramipril 1.25 mg capsule1.59USD capsule
Altace 10 mg Tablet1.14USD tablet
Altace 2.5 mg Tablet0.9USD tablet
Altace 5 mg Tablet0.9USD tablet
Altace 1.25 mg Tablet0.78USD tablet
Apo-Ramipril 10 mg Tablet0.64USD tablet
Co Ramipril 10 mg Tablet0.64USD tablet
Jamp-Ramipril 10 mg Tablet0.64USD tablet
Mylan-Ramipril 10 mg Tablet0.64USD tablet
Novo-Ramipril 10 mg Tablet0.64USD tablet
Pms-Ramipril 10 mg Tablet0.64USD tablet
Ramipril 10 mg Tablet0.64USD tablet
Ran-Ramipril 10 mg Tablet0.64USD tablet
Ratio-Ramipril 10 mg Tablet0.64USD tablet
Sandoz Ramipril 10 mg Tablet0.64USD tablet
Apo-Ramipril 2.5 mg Tablet0.5USD tablet
Apo-Ramipril 5 mg Tablet0.5USD tablet
Co Ramipril 2.5 mg Tablet0.5USD tablet
Co Ramipril 5 mg Tablet0.5USD tablet
Jamp-Ramipril 2.5 mg Tablet0.5USD tablet
Jamp-Ramipril 5 mg Tablet0.5USD tablet
Mylan-Ramipril 2.5 mg Tablet0.5USD tablet
Mylan-Ramipril 5 mg Tablet0.5USD tablet
Novo-Ramipril 2.5 mg Tablet0.5USD tablet
Novo-Ramipril 5 mg Tablet0.5USD tablet
Pms-Ramipril 2.5 mg Tablet0.5USD tablet
Pms-Ramipril 5 mg Tablet0.5USD tablet
Ramipril 2.5 mg Tablet0.5USD tablet
Ramipril 5 mg Tablet0.5USD tablet
Ran-Ramipril 2.5 mg Tablet0.5USD tablet
Ran-Ramipril 5 mg Tablet0.5USD tablet
Ratio-Ramipril 2.5 mg Tablet0.5USD tablet
Ratio-Ramipril 5 mg Tablet0.5USD tablet
Sandoz Ramipril 2.5 mg Tablet0.5USD tablet
Sandoz Ramipril 5 mg Tablet0.5USD tablet
Apo-Ramipril 1.25 mg Tablet0.44USD tablet
Co Ramipril 1.25 mg Tablet0.44USD tablet
Jamp-Ramipril 1.25 mg Tablet0.44USD tablet
Mylan-Ramipril 1.25 mg Tablet0.44USD tablet
Pms-Ramipril 1.25 mg Tablet0.44USD tablet
Ramipril 1.25 mg Tablet0.44USD tablet
Ran-Ramipril 1.25 mg Tablet0.44USD tablet
Ratio-Ramipril 1.25 mg Tablet0.44USD tablet
Sandoz Ramipril 1.25 mg Tablet0.44USD tablet
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5403856No1995-04-042012-04-04US flag
CA2382387No2005-06-212020-08-25Canada flag
CA1338344No1996-05-212013-05-21Canada flag
US7368469No2008-05-062020-08-30US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)109 °CPhysProp
water solubility3.5mg/LNot Available
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 mg/mLALOGPS
logP0.92ALOGPS
logP1.47ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity111.19 m3·mol-1ChemAxon
Polarizability44.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9159
Blood Brain Barrier-0.8726
Caco-2 permeable-0.8491
P-glycoprotein substrateSubstrate0.7263
P-glycoprotein inhibitor INon-inhibitor0.7002
P-glycoprotein inhibitor IIInhibitor0.6295
Renal organic cation transporterNon-inhibitor0.8869
CYP450 2C9 substrateNon-substrate0.8541
CYP450 2D6 substrateNon-substrate0.8969
CYP450 3A4 substrateNon-substrate0.5082
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9304
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5691
Ames testNon AMES toxic0.9108
CarcinogenicityNon-carcinogens0.9267
BiodegradationNot ready biodegradable0.8903
Rat acute toxicity1.6732 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.98
hERG inhibition (predictor II)Non-inhibitor0.7901
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00lr-3930000000-ea57777ac9a14b1e9083

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Levitt DG, Schoemaker RC: Human physiologically based pharmacokinetic model for ACE inhibitors: ramipril and ramiprilat. BMC Clin Pharmacol. 2006 Jan 6;6:1. [PubMed:16398929]
  3. Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016]
  4. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Peptide binding
Specific Function
This is a receptor for bradykinin. Could be a factor in chronic pain and inflammation.
Gene Name
BDKRB1
Uniprot ID
P46663
Uniprot Name
B1 bradykinin receptor
Molecular Weight
40494.29 Da
References
  1. Ignjatovic T, Tan F, Brovkovych V, Skidgel RA, Erdos EG: Novel mode of action of angiotensin I converting enzyme inhibitors: direct activation of bradykinin B1 receptor. J Biol Chem. 2002 May 10;277(19):16847-52. Epub 2002 Mar 5. [PubMed:11880373]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Shah GB, Sharma S, Mehta AA, Goyal RK: Oculohypotensive effect of angiotensin-converting enzyme inhibitors in acute and chronic models of glaucoma. J Cardiovasc Pharmacol. 2000 Aug;36(2):169-75. [PubMed:10942157]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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