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Quinapril
ACCUPRIL · Asig · CI-906 · Ectren · ACCUPRO · Koretic · ACCUPRIN · Quniapril
Identifikatoren & physikalische Daten
| CAS No. | 85441-61-8 |
|---|---|
| Summenformel | C25H30N2O5 |
| Durchschnittliche Molmasse | 438,5 g/mol |
| Monoisotopische Masse | 438,21547206 g/mol |
| SMILES | CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1Cc2ccccc2C[C@H]1C(=O)O |
| InChIKey | JSDRRTOADPPCHY-HSQYWUDLSA-N |
| PubChem CID | 54892 |
| ChEMBL | CHEMBL1592 |
| ChEBI | CHEBI:8713 |
| DTXSID | DTXSID4023547 |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 95,9 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 10 |
| Schwere Atome | 32 |
| Formalladung | 0 |
| Komplexität | 648 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antihypertensives |
| LogP (Verteilungskoeffizient) | 3.2 |
| Löslichkeit | 8.50e-03 g/L |
| Human Drugs | Breast FeedingLactationMilk, HumanAntihypertensive AgentsAngiotensin-Converting Enzyme InhibitorsACE InhibitorsACEIs |
| Schmelzpunkt | 120-130 °C120 - 130 °C120-130°C |
| Physical Description | Solid |
| Dissociation Constants | 2.8 |
| Collision Cross Section | 205.79 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]204.4 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated] |
| Siedepunkt | 662.0±55.0 °C(Predicted) |
| Dichte | 1.217±0.06 g/cm3(Predicted) |
| pKa (Säurekonstante) | 3.39±0.20(Predicted) |
| BCS Class | 1 |
| CAS Datenbank | 85441-61-8(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Regulatorische Informationen | Quinapril: 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. |
|---|---|
| Hepatotoxicity | Quinapril, like other ACE inhibitors, has been associated with a low rate of serum aminotransferase elevations ( |
| Unerwünschte Wirkungen | Adverse effects of quinapril include dry cough (as is typical among all ACEi class members), hyperkalemia, angioedema, dizziness, hypotension, and renal dysfunction. Less common adverse effects include skin rash and dysgeusia. Angioedema is a rare but well-documented adverse effect of ACEi, which often presents as facial, tongue, and lip swelling. However, unique instances present with isolated swelling of the small bowel. This presentation, also called intestinal-type angioedema, may manifest in patients taking ACEi presenting with abdominal pain, nausea, vomiting, and diarrhea. Although one report of agranulocytosis is available in a neutropenic patient using quinapril, no other reports of agranulocytosis were noted in the literature, as found in rare cases of captopril use, one of the original ACE inhibitors. |
| Expositionspfade | Peak plasma concentrations of quinapril occur within one hour following oral administration. The extent of absorption is at least 60%. The rate and extent of quinapril absorption are diminished moderately (approximately 25-30%) when ACCUPRIL tablets are administered during a high-fat meal. |
| Toxizitätsübersicht | Overdosing ACEi may lead to significant hypotension, renal failure, hyperkalemia, and hyponatremia. After ingesting 20 times the daily amount, significant hypotension occurred within the first 6 hours of ingestion. Clinicians could consider activated charcoal if a patient presents within an hour of ingestion. To date, no true antidote for quinapril is available.There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Quinaprilat, the principle active metabolite of quinapril, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Quinaprilat also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors. |
Anwendungen & Verwendung
Beschreibung
Quinapril is an orally active, non-sulfhydryl ACE inhibitor reportedly useful in the treatment of essential hypertension. The main claimed advantage of quinapril compared with other available ACE inhibitors is its side-effect profile. It is also effective in the management of congestive heart failure.
Verwenden
Antihypertensive; enzyme inhibitor (angiotensin-converting).