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Ramipril
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| Systematic (IUPAC) name | |
| (1S,5S,7S)-8-[(2S)-2-[[(1S)-1-ethoxycarbonyl-3-phenyl- propyl]amino]propanoyl]-8-azabicyclo[3.3.0]octane-7- carboxylic acid |
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| Identifiers | |
| CAS number | |
| ATC code | C09 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C23H32N2O5 |
| Mol. mass | 416.511 g/mol |
| SMILES | & |
| 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%) |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | Oral |
Ramipril (marketed as Tritace/Ramace or Altace) is an angiotensin-converting enzyme (ACE) inhibitor, used to treat hypertension and congestive heart failure. ACE inhibitors lower the production of angiotensin II, therefore relaxing arterial muscles while at the same time 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.
Ramipril is a prodrug and is converted to the active metabolite ramiprilat by liver esterase enzymes. 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.
It is marketed by King Pharmaceuticals under the brand name Altace and was protected by the U.S. Patent No. 5,061,722 (was scheduled to expire on 29th Oct, 2008) assigned to Aventis. On September 11, 2007 in an appeal by Lupin Pharmaceuticals the United States Court of Appeals for the Federal Circuit reversed a district court trial verdict, finding that Aventis's patent on Altace was invalid for obviousness - opening the gate of this medicine to generic manufacturers.
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Indications
Indications for its use include:
- Hypertension;
- Congestive heart failure;
- Following myocardial infarction in patients with clinical evidence of heart failure;
- Susceptible patients over 55 years: prevention of myocardial infarction, stroke, cardiovascular death or need of revascularization procedures.
Cautions
- Do not take potassium supplements without seeking medical advice.
- Do not take during pregnancy
Contraindications
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.
Side-effects
- may cause swelling of the mouth, tongue, or throat
- low blood sugar in patients taking other medicine for diabetes which shows as sweating or shakiness
- Dry cough may develop, dizziness, and light-headedness due to low blood pressure. (It is recommended to start treatment with the lowest dose.)
Dose
Patients are started on the lowest dose and titrated up every 1 - 2 weeks as required.
See also
External links
- Altace (ramipril), a registered trademark of King Pharmaceuticals, Inc.
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Wikipedia content modification information:
- This page was last modified on 17 June 2008, at 21:57.
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