Altace

Ramipril

Clinical data
Trade names	Altace
AHFS/Drugs.com	Monograph
MedlinePlus	a692027
Pregnancy category	D
Routes of administration	Oral
ATC code	C09AA05 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	28%
Protein binding	73% (ramipril) 56% (ramiprilat)
Metabolism	Hepatic, to ramiprilat
Biological half-life	2 to 4 hours
Excretion	Renal (60%) and fecal (40%)
Identifiers
IUPAC name (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
CAS Number	87333-19-5 Y
PubChem CID	5362129
IUPHAR/BPS	6339
DrugBank	DB00178 Y
ChemSpider	4514937 Y
UNII	L35JN3I7SJ
KEGG	D00421 Y
ChEBI	CHEBI:8774 Y
ChEMBL	CHEMBL1168 Y
ECHA InfoCard	100.170.726
Chemical and physical data
Formula	C23H32N2O5
Molar mass	416.511 g/mol
3D model (JSmol)	Interactive image
Melting point	109 °C (228 °F)
SMILES O=C(OCC)[C@@H](N[C@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@H]12)C)CCc3ccccc3
InChI InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1 Y Key:HDACQVRGBOVJII-JBDAPHQKSA-N Y

Ramipril, sold under the brand name Altace among others, is an angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure (hypertension) and congestive heart failure. By inhibiting an enzyme, ACE inhibitors relax the muscles around small arteries (arterioles). The arterioles expand and allow blood to flow through more easily. This reduces blood pressure.

Indications for its use include:

Contraindications to its use include renovascular disease (impaired blood flow in the kidneys), severe renal impairment (especially in patients with one kidney or with bilateral renal artery stenosis), volume-depleted patients, a history of angioedema while on an ACE inhibitors, pregnancy, and 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 a rash or swelling of the face, mouth, tongue, or throat. In extreme cases, ramipril may lead to potentially fatal liver problems.

ACE inhibitors inhibit the actions of angiotensin converting enzyme (ACE), thereby lowering the production of angiotensin II and decreasing the breakdown of bradykinin. The decrease in angiotensin II results in relaxation of arteriole smooth muscle leading to a decrease in total peripheral resistance, reducing blood pressure as the blood is pumped through widened vessels. Its effect on bradykinin is responsible for the dry cough side effect.

Ramipril, a prodrug or precursor drug, is converted to the active metabolite ramiprilat by carboxylesterase 1. Ramiprilat is mostly excreted by the kidneys. Its half-life is variable (3–16 hours), and is prolonged by heart and liver failure, as well as kidney failure.