Ramipril

HCID 5362129CAS 87333-19-5

基本情報

標準SMILES
CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21
InChIKey
HDACQVRGBOVJII-JBDAPHQKSA-N
分子式
C23H32N2O5
平均分子量
416.5 g/mol
単同位体質量
416.23112212

概要

Ramipril is 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. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, a prodrug, a matrix metalloproteinase inhibitor, a cardioprotective agent and a bradykinin receptor B2 agonist. It is an ethyl ester, a dicarboxylic acid monoester, an azabicycloalkane, a cyclopentapyrrole and a dipeptide. It is a conjugate acid of a ramipril(1-).

名称と識別子

優先名称
Ramipril
IUPAC
(2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid

名称と別名

ramipril87333-19-5AltaceTritaceTriatecRamaceVesdilDelixCardaceAcovilPramaceHoe-498
名称をさらに表示
RamiprilumUniprilRamiprilum [Latin]HOE 498CorprilRamipresEcatorHopace

データベース識別子

CAS
87333-19-5
PubChem CID
5362129
DTXSID
DTXSID8023551
ChEMBL
CHEMBL1168
ChEBI
CHEBI:8774
UNII
L35JN3I7SJ
EC Number
642-904-3
Nikkaji
J22.246A

物性

構造計算による物性

XLogP
1.4
極性表面積
95.9 Ų
水素結合供与体数
2
水素結合受容体数
6
回転可能結合数
10
重原子数
30

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Antihypertensives

Pharmaceuticals -> Listed in ZINC15

LogP · 2 件

2.9

1.05

Color/Form · 2 件

Felty needles from ether

White crystalline solid

Solubility · 6 件

3.5mg/L

Sparingly soluble in water

Freely soluble in methanol

Soluble in polar substances and buffered aqueous solutions

3.90e-02 g/L

>62.5 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 3 件

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Angiotensin-Converting Enzyme Inhibitors; ACE Inhibitors; ACEIs

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 1.3% (1 of 76) of reports.

Danger

H360 (93.4%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 76 reports by companies from 13 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationRamipril: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
FDA Requirements · 1 件

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including ramipril, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Hazard Classes and CategoriesRepr. 1B (93.4%)
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents.

安全と保護具

Fire Fighting Procedures · 2 件

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage Conditions · 2 件

Store at 20 deg to 25 °C (68 deg to 77 °F).

Keep container tightly closed in a dry and well-ventilated place.

Cleanup Methods · 1 件

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Disposal Methods · 2 件

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Preventive Measures · 5 件

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Precautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: General industrial hygiene practice.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Personal Protective Equipment (PPE) · 4 件

Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place.

Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

毒性情報

Interactions · 4 件

In patients who are elderly, volume-depleted (including those on diuretic therapy), or with compromised renal function, co-administration of non-ateroidal anti-inflammatory drugs (NSAIDs), including selective cyclooxygenase-2 (COX-2) inhibitors, with angiotensin-converting enzyme (ACE) inhibitors, including ramipril, may result in deterioration of renal function, including possible acute renal failure. These effects are usually reversible. Monitor renal function periodically in patients receiving ramipril and NSAID therapy. The antihypertensive effect of ACE inhibitors, including ramipril, may be attenuated by NSAIDs.

Increased serum lithium levels and symptoms of lithium toxicity have been reported in patients receiving ACE inhibitors during therapy with lithium; therefore, frequent monitoring of serum lithium levels is recommended. If a diuretic is also used, the risk of lithium toxicity may be increased.

Coadministration of ramipril with other drugs that raise serum potassium levels may result in hyperkalemia. Monitor serum potassium in such patients.

Patients on diuretics, especially those in whom diuretic therapy was recently instituted, may occasionally experience an excessive reduction of blood pressure after initiation of therapy with ramipril. The possibility of hypotensive effects with ramipril can be minimized by either decreasing or discontinuing the diuretic or increasing the salt intake prior to initiation of treatment with ramipril. If this is not possible, reduce the starting dose.

HepatotoxicityRamipril, like other ACE inhibitors, has been associated with a low rate of serum aminotransferase elevations (
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2000(SRC), determined from a structure estimation method(2), indicates that ramipril is expected to have low mobility in soil(SRC). The estimated pKa values of ramipril are 3.74 and 5.15(3), indicating that this compound will exist almost entirely exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Ramipril is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.8X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2017).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2000(SRC), determined from a structure estimation method(2), indicates that ramipril is expected to adsorb to suspended solids and sediment(SRC). Estimated pKa values of 3.74 and 5.15(3) indicate ramipril will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of 3.32(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2017).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ramipril, which has an estimated vapor pressure of 3.8X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase ramipril may be removed from the air by wet and dry deposition(SRC). Ramipril contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsThe following adverse reactions have been associated with ramipril administration.
Milk Concentrations/MILK/ Ingestion of a single 10 mg oral dose of ramipril resulted in undetectable amounts of ramipril and its metabolites in breast milk.
Toxicity Summary · 2 件

IDENTIFICATION AND USE: Ramipril is a prodrug and has little pharmacologic activity until hydrolyzed in the liver to ramiprilat. It is an angiotensin-converting enzyme (ACE) inhibitor indicated for the treatment of hypertension. It is also used for stable patients with demonstratable congestive heart failure within the first few days of sustaining acute myocardial infarction. HUMAN STUDIES: Rare ACE inhibitor-associated clinical syndrome manifested initially by cholestatic jaundice may occur. It may progress to fulminant hepatic necrosis and is potentially fatal. Patients receiving an ACE inhibitor, including ramipril, who develop jaundice or marked elevations in hepatic enzymes should discontinue the drug and receive appropriate monitoring. Sensitivity reactions, including anaphylactic reactions and angioedema (including laryngeal or tongue edema) are potentially fatal. Head and neck angioedema involving the tongue, glottis, or larynx may cause airway obstruction. If laryngeal stridor or angioedema of the face, tongue, or glottis occurs, ramipril should be discontinued and appropriate therapy (e.g., epinephrine) should be initiated immediately. Use of drugs that act on the renin-angiotensin system during the second and third trimesters of pregnancy reduces fetal renal function and increases fetal and neonatal morbidity and death. Resulting oligohydramnios can be associated with fetal lung hypoplasia and skeletal deformations. Potential neonatal adverse effects include skull hypoplasia, anuria, hypotension, renal failure, and death. When pregnancy is detected, discontinue ramipril as soon as possible. No mutagenic activity was detected in the unscheduled DNA synthesis in a human cell line. ANIMAL STUDIES: No evidence of a tumorigenic effect was found when ramipril was given by gavage to rats for up to 24 months at doses of up to 500 mg/kg/day or to mice for up to 18 months at doses of up to 1000 mg/kg/day. A study in rats with dosages as great as 500 mg/kg/day did not produce adverse effects on fertility. Kidney organogenesis and functional development continue well into the postnatal period in the rat. A within-litter design was used to characterize renal susceptibility to an ACE inhibitor during the third week of life in rats. There were no treatment-related effects in rats dosed on PND 21. Following dosing on PND 14, dose-related increases were noted in mean serum urea nitrogen and/or creatinine levels on PND 17, but these measures recovered by PND 28. The interim changes were accompanied by macroscopic and microscopic changes in the kidneys on PND 17, including tubular hypoplasia, renal papillary edema, cortical tubular dilatation, hydronephrosis (pelvic dilatation) and tubular basophilia; renal anatomic changes were still evident and more severe on PND 28, 14 days after dosing. No mutagenic activity was detected in the Ames test in bacteria, the micronucleus test in mice or a forward gene-mutation assay in a Chinese hamster ovary cell line.

Ramipril overdose can lead to severe hypotension, primarily attributed to vasodilation and effective hypovolemia. A study conducted in 2006 to investigate the effects of ramipril overdose on blood pressure concluded that a drop in blood pressure typically occurs within the first 4 to 4.5 hours after ingestion. Therefore, monitoring the patient for at least 6 hours after the overdose is essential. If the blood pressure remains stable during the first 6 hours after administration, the patient can be considered for discharge.

法規制情報

FDA Requirements · 1 件

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including ramipril, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

化学と産業

薬理情報

ATC Code · 3 件

C09AA05

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingProtein binding of ramipril is about 73% and that of ramiprilat about 56%. Protein binding is independent of concentration over the range of 0.1μg/mL-10μg/mL
Pharmacodynamics · 1 件

Ramipril is an ACE inhibitor similar to benazepril, fosinopril and quinapril. 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 · 1 件

Ramipril inhibits the RAAS system by binding to and inhibiting ACE thereby preventing the conversion of angiotensin I to angiotensin II. As plasma levels of angiotensin II fall, less activation of the G-protein coupled receptors angiotensin receptor I (AT<sub>1</sub>R) and angiotensin receptor II (AT<sub>2</sub>R) occurs. AT<sub>1</sub>R mediates vasoconstriction, inflammation, fibrosis, and oxidative stress through a variety of signaling pathways. These include G<sub>q</sub> coupling to the inositol triphosphate pathway, activation of phospholipases C, A<sub>2</sub>, and D which contribute to eicosanoid production, activation of Ca<sup>2+</sup>-dependent and MAP kinases, G<sub>i</sub> and G<sub>12/13</sub>, and eventual activation of the Jak/STAT pathway leading to cell growth and production of extracellular matrix components. AT<sub>1</sub>R 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. AT<sub>2</sub>R acts in opposition to the effects of AT<sub>1</sub>R by activating phosphotyrosine phosphatases which inhibit MAP kinases, inhibiting Ca<sup>2+</sup> channel opening, and stimulating cGMP and nitric oxide production leading to vasodilation. 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 AT<sub>2</sub>R although the bulk of its effect is mediated by MasR. ACE is also responsible for the breakdown of bradykinin. 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.

Biological Half-Life · 2 件

Plasma concentrations of ramiprilat decline in a triphasic manner. 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.

Plasma concentrations of ramiprilat /metabolite of ramipril/ decline in a triphasic manner (initial rapid decline, apparent elimination phase, terminal elimination phase). The initial rapid decline, which represents distribution of the drug into a large peripheral compartment and subsequent binding to both plasma and tissue ACE, has a half-life of 2 to 4 hours. Because of its potent binding to ACE and slow dissociation from the enzyme, ramiprilat shows two elimination phases. The apparent elimination phase corresponds to the clearance of free ramiprilat and has a half-life of 9 to 18 hours. The terminal elimination phase has a prolonged half-life (>50 hours) and probably represents the binding/dissociation kinetics of the ramiprilat/ACE complex. It does not contribute to the accumulation of the drug. After multiple daily doses of ramipril 5 mg to 10 mg, the half-life of ramiprilat concentrations within the therapeutic range was 13 to 17 hours. /Ramiprilat/

Metabolism/Metabolites · 5 件

Hepatic metabolism accounts for 75% of total ramipril metabolism. 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.

Cleavage of the ester group (primarily in the liver) converts ramipril to its active diacid metabolite, ramiprilat. Peak plasma concentrations of ramiprilat are reached 2 to 4 hours after drug intake. The serum protein binding of ramipril is about 73% and that of ramiprilat about 56%; in vitro, these percentages are independent of concentration over the range of 0.01 ug/mL to 10 mcg/mL.

After oral administration to dogs, ramipril is rapidly converted via de-esterification into ramiprilat. Bioavailability of ramiprilat after a dose of 0.25 mg/kg per day of ramipril is approximately 6.7%.

Ramipril is a prodrug and has little pharmacologic activity until hydrolyzed in the liver to ramiprilat.

Ramipril is almost completely metabolized to ramiprilat, which has about 6 times the angiotensin-converting enzyme (ACE) inhibitory activity of ramipril, and to the diketopiperazine ester, the diketopiperazine acid, and the glucuronides of ramipril and ramiprilat, all of which are inactive.

用途と製造

Uses · 4 件

MEDICATION

MEDICATION (VET)

Angiotensin-Converting Enzyme Inhibitors; Antihypertensive Agents

Use (kg; approx.) in Germany (2009): >10000

Methods of ManufacturingPreparation: V. Teetz et al., European Patent Office patent 79022 (1983 to Hoechst) ... E. H. Gold et al., United States of America patent 4587258 (1986 to Schering Corp.).
Formulations/PreparationsTable: Ramipril Preparations [Table#8439]

関連反応

1 件

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