Ramipril 1267081 220016091 2008-06-17T21:57:20Z DumZiBoT 6085301 robot Adding: [[it:Ramipril]] {{Refimprove|date=November 2007}} {{drugbox | IUPAC_name = (1''S'',5''S'',7''S'')-8-[(2''S'')-2-<nowiki>[[</nowiki>(1''S'')-1-ethoxycarbonyl-3-phenyl-<br>propyl]amino]propanoyl]-8-azabicyclo[3.3.0]octane-7-<br>carboxylic acid | image = Ramipril.svg | CAS_number = 87333-19-5 | ATC_prefix = C09 | ATC_suffix = AA05 | ATC_supplemental = | PubChem = 5362129 | DrugBank = APRD00009 | C = 23 | H = 32 | N = 2 | O = 5 | molecular_weight = 416.511 g/mol | smiles = CCOC(=O)[C@H](CCc1ccccc1)N[C@H](C)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(=O)O | bioavailability = 28% | protein_bound = 73% (ramipril)<br>56% (ramiprilat) | metabolism = [[Liver|Hepatic]], to ramiprilat | elimination_half-life = 2 to 4 hours | excretion = [[Kidney|Renal]] (60%) and fecal (40%) | pregnancy_category = D | legal_UK = POM | legal_US = Rx-only | routes_of_administration = Oral }} '''Ramipril''' (marketed as '''Tritace/Ramace''' or '''Altace''') is an [[ACE inhibitor|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]] [[enzyme]]s. Ramiprilat is mostly [[excretion|excreted]] by the [[kidney]]s. The [[half-life]] of ramiprilat is variable (3-16 hours), and is prolonged by heart and [[liver failure]], as well as [[renal failure|kidney failure]]. It is marketed by [[King Pharmaceuticals]] under the brand name [http://www.altace.com Altace] and was protected by the U.S. Patent No. [http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=5061722.PN.&OS=PN/5061722&RS=PN/5061722 5,061,722] (was scheduled to expire on 29<sup>th</sup> Oct, 2008) assigned to [[Aventis]]. On September 11, 2007 in an appeal by [http://www.lupinpharmaceuticals.com/ 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 [http://www.cafc.uscourts.gov/opinions/06-1530.pdf invalid for obviousness] - opening the gate of this medicine to generic manufacturers. ==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== *[[Hypertension]] *[[Hypotension]] *[[Heart failure]] *[[Chest Pains]] ==External links== *[http://www.altace.com Altace (ramipril)], a registered trademark of [[King Pharmaceuticals]], Inc. {{ACE inhibitors}} [[Category:ACE inhibitors]] [[Category:Prodrugs]] [] [[de:Ramipril]] [[hr:Ramipril]] [[it:Ramipril]] [[hu:Ramipril]]