Ramipril

Ramipril
Clinical data
Trade names	Altace, others
AHFS/Drugs.com	Monograph
MedlinePlus	a692027
License data	US DailyMed: Ramipril;
Routes of; administration	By mouth
ATC code	C09AA05 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	28%
Protein binding	73% (ramipril); 56% (ramiprilat)
Metabolism	Liver, to ramiprilat
Elimination half-life	13 to 17 hours
Excretion	Kidney (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 ;
PubChem CID	5362129;
IUPHAR/BPS	6339;
DrugBank	DB00178 ;
ChemSpider	4514937 ;
UNII	L35JN3I7SJ;
KEGG	D00421 ;
ChEBI	CHEBI:8774 ;
ChEMBL	ChEMBL1168 ;
CompTox Dashboard (EPA)	DTXSID8023551 ;
ECHA InfoCard	100.170.726
Chemical and physical data
Formula	C23H32N2O5
Molar mass	416.518 g·mol−1
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 ; Key:HDACQVRGBOVJII-JBDAPHQKSA-N ;
	(verify)

Ramipril, sold under the brand name Altace among others, is an ACE inhibitor type medication used to treat high blood pressure, heart failure, and diabetic kidney disease.^[1] It can also be used as a preventative medication in patients over 55 years old to reduce the risk of having a heart attack, stroke or cardiovascular death in patients shown to be at high risk, such as some diabetics and patients with vascular disease.^[2]^[3]^[4] It is a reasonable initial treatment for high blood pressure.^[1] It is taken by mouth.^[1]

Common side effects include headaches, dizziness, fatigue, and cough.^[1] Serious side effects may include liver problems, angioedema, kidney problems, and high blood potassium.^[1] Use in pregnancy and breastfeeding is not recommended.^[5] It is an ACE inhibitor and works by decreasing renin-angiotensin-aldosterone system activity.^[1]

Ramipril was patented in 1981 and approved for medical use in 1989.^[6] It is available as a generic medication.^[7] In 2022, it was the 187th most commonly prescribed medication in the United States, with more than 2 million prescriptions.^[8]^[9]

^ ^a ^b ^c ^d ^e ^f "Ramipril Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
^ Yusuf S, Sleight P, Pogue J, Bosch J, Davies R, Dagenais G (January 2000). "Effects of an angiotensin-converting-enzyme inhibitor, ramipril, on cardiovascular events in high-risk patients". The New England Journal of Medicine. 342 (3): 145–53. doi:10.1056/NEJM200001203420301. PMID 10639539.
^ HOPE study investigators (January 2000). "Effects of ramipril on cardiovascular and microvascular outcomes in people with diabetes mellitus: results of the HOPE study and MICRO-HOPE substudy". The Lancet. 355 (9200): 253–259. doi:10.1016/S0140-6736(99)12323-7. S2CID 1863533.
^ Savarese G, Costanzo P, Cleland JG, Vassallo E, Ruggiero D, Rosano G, et al. (January 2013). "A meta-analysis reporting effects of angiotensin-converting enzyme inhibitors and angiotensin receptor blockers in patients without heart failure". Journal of the American College of Cardiology. 61 (2): 131–42. doi:10.1016/j.jacc.2012.10.011. PMID 23219304.
^ "Ramipril Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 469. ISBN 9783527607495.
^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 172–173. ISBN 9780857113382.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Ramipril Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[AHFS2019-1] ^ ^a ^b ^c ^d ^e ^f "Ramipril Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.

[2] Yusuf S, Sleight P, Pogue J, Bosch J, Davies R, Dagenais G (January 2000). "Effects of an angiotensin-converting-enzyme inhibitor, ramipril, on cardiovascular events in high-risk patients". The New England Journal of Medicine. 342 (3): 145–53. doi:10.1056/NEJM200001203420301. PMID 10639539.

[3] HOPE study investigators (January 2000). "Effects of ramipril on cardiovascular and microvascular outcomes in people with diabetes mellitus: results of the HOPE study and MICRO-HOPE substudy". The Lancet. 355 (9200): 253–259. doi:10.1016/S0140-6736(99)12323-7. S2CID 1863533.

[4] Savarese G, Costanzo P, Cleland JG, Vassallo E, Ruggiero D, Rosano G, et al. (January 2013). "A meta-analysis reporting effects of angiotensin-converting enzyme inhibitors and angiotensin receptor blockers in patients without heart failure". Journal of the American College of Cardiology. 61 (2): 131–42. doi:10.1016/j.jacc.2012.10.011. PMID 23219304.

[Preg2019-5] "Ramipril Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.

[Fis2006-6] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 469. ISBN 9783527607495.

[BNF76-7] British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 172–173. ISBN 9780857113382.

[8] "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.

[9] "Ramipril Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

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