Lisinopril

Lisinopril

Chemical structure of lisinopril
Clinical data
Pronunciation	/laɪˈsɪnəprɪl/, ly-SIN-ə-pril
Trade names	Prinivil, Zestril, others
AHFS/Drugs.com	Monograph
MedlinePlus	a692051
Pregnancy category	D (not recommended)
Routes of administration	By mouth
ATC code	C09AA03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	approx. 25%, but wide range between individuals (6 to 60%)
Protein binding	0
Metabolism	None
Biological half-life	12 hours
Excretion	Eliminated unchanged in urine
Identifiers
IUPAC name (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
Synonyms	(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
CAS Number	83915-83-7
PubChem CID	5362119
IUPHAR/BPS	6360
DrugBank	APRD00560 Y
ChemSpider	4514933 Y
UNII	7Q3P4BS2FD
KEGG	D00362 Y
ChEBI	CHEBI:43755 N
ChEMBL	CHEMBL1237 Y
PDB ligand	LPR (PDBe, RCSB PDB)
ECHA InfoCard	100.155.382
Chemical and physical data
Formula	C21H31N3O5
Molar mass	405.488 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)[C@H]2N(C(=O)[C@@H](N[C@H](C(=O)O)CCc1ccccc1)CCCCN)CCC2
InChI InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1 Y Key:RLAWWYSOJDYHDC-BZSNNMDCSA-N Y
NY (what is this?)

Lisinopril is a drug of the angiotensin-converting enzyme (ACE) inhibitor class used primarily in treatment of high blood pressure, heart failure, and after heart attacks. It is also used for preventing kidney and eye complications in people with diabetes. Its indications, contraindications, and side effects are as those for all ACE inhibitors.

Lisinopril was the third ACE inhibitor (after captopril and enalapril) and was introduced into therapy in the early 1990s. A number of properties distinguish it from other ACE inhibitors: It is hydrophilic, has a long half-life and tissue penetration, and is not metabolized by the liver.

Lisinopril is typically used for the treatment of hypertension, congestive heart failure, acute myocardial infarction, and diabetic nephropathy.

Treatment with lisinopril should be avoided for people who have a history of angioedema (hereditary or idiopathic) or who have diabetes and are taking aliskiren.

Side effects, incidence differs depending on which disease state the patient is being treated for.

People taking lisinopril for the treatment of hypertension may experience the following side effects: