| Systematic (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 | |
| Clinical data | |
| Trade names | Altace |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a692027 |
| Pregnancy cat. | D |
| Legal status | POM (UK) ℞-only (US) |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 28% |
| Protein binding | 73% (ramipril) 56% (ramiprilat) |
| Metabolism | Hepatic, to ramiprilat |
| Half-life | 2 to 4 hours |
| Excretion | Renal (60%) and fecal (40%) |
| Identifiers | |
| CAS number | 87333-19-5 |
| ATC code | C09AA05 |
| PubChem | CID 5362129 |
| DrugBank | APRD00009 |
| ChemSpider | 4514937 |
| UNII | L35JN3I7SJ |
| KEGG | D00421 |
| ChEBI | CHEBI:8774 |
| ChEMBL | CHEMBL1168 |
| Chemical data | |
| Formula | C23H32N2O5 |
| Mol. mass | 416.511 g/mol |
| SMILES | eMolecules & PubChem |
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Ramipril (marketed as Prilace by Arrow Pharmaceuticals in Australia, Ramipro by Westfield Pharma in the Philippines, Tritace by Sanofi-Aventis and Altace by King Pharmaceuticals in the United States) is an angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.
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ACE inhibitors lower the production of angiotensin II and also decrease the breakdown of bradykinin, thereby relaxing arterial muscles and enlarging the arteries, allowing the heart to pump blood more easily, and increasing blood flow due to more blood being pumped into and through larger passageways. Its effect on bradykinin is also responsible for the dry cough side effect.
Ramipril is a prodrug and is converted to the active metabolite ramiprilat by liver esterase enzymes.[1] Ramiprilat is mostly excreted by the kidneys. The half-life of ramiprilat is variable (3–16 hours), and is prolonged by heart and liver failure, as well as kidney failure.
The compound was protected by U.S. Patent 5,061,722 which was assigned to Aventis on 29 October 1991. The patent was scheduled to expire on 29 October 2008. On 11 September 2007, in an appeal by the Indian company Lupin Ltd., the United States Court of Appeals for the Federal Circuit reversed a district court trial verdict and found that Aventis's patent on Ramipril was invalid for obviousness - opening the gate of this medicine to generic manufacturers.
Ramipril is marketed in India under the brand names of Cardace, Zigpril and Zorem.
Indications for its use include:
Renovascular disease, severe renal impairment (especially in patients with one kidney or with bilateral renal artery stenosis), volume-depleted patients, history of angioedema while on an ACE inhibitor, pregnancy, hypotension.
Serious allergic reactions to this drug are unlikely, but immediate medical attention must be sought if they occur. Symptoms of a serious allergic reaction include but are not limited to:
In extreme cases, Ramipril may lead to potentially fatal liver problems. It is recommended to start treatment with the lowest dose.
Patients are started on the lowest dose and titrated up every 3 – 4 weeks as required.
Dosage comes in the following forms: 1.25 mg, 2.5 mg, 5 mg, 10 mg
The HOPE trial[4][5] seemed to show that ramipril possessed cardioprotective qualities which extended beyond its qualities as an anti-hypertensive. The HOPE trial and the interpretation of the results have been criticised.[6]
The AIRE trial[1][7] showed a 27% reduction in mortality.
Ramipril was found to have similar results as telmisartan.[8]
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