Lisinopril

Structural formula
General
Non-proprietary name	Lisinopril
other names	(all- S ) -1- [6-Amino-2- (1-carboxy-3-phenyl-propyl) amino-hexanoyl] pyrrolidine-2-carboxylic acid (dihydrate) (all- S ) -1- {6-Amino-2 - [(1-carboxy-3-phenylpropyl) amino] hexanoyl} pyrrolidine-2-carboxylic acid ( IUPAC )
Molecular formula	C 21 H 31 N 3 O 5 (Lisinopril) C 21 H 31 N 3 O 5 · 2H 2 O (lisinopril dihydrate)
External identifiers / databases
CAS number 76547-98-3 (lisinopril) 83915-83-7 (lisinopril dihydrate) EC number 278-488-1 ECHA InfoCard 100,071,332 PubChem 5362119 ChemSpider 4514933 DrugBank DB00722 Wikidata Q412208
Drug information
ATC code	C09 AA03
Drug class	ACE inhibitors
Mechanism of action	Inhibition of the angiotensin converting enzyme
properties
Molar mass	405.49 g mol −1 (lisinopril) 441.52 g mol −1 (lisinopril dihydrate)
solubility	readily soluble in water (97 mg ml −1 ) and methanol (14 mg ml −1 ), poorly soluble (<0.1 mg ml −1 each ) in ethanol, acetone, acetonitrile, chloroform and dimethylformamide (lisinopril Dihydrate)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Dihydrate no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	3600 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lisinopril is a drug in the group of ACE inhibitors that is used in particular to treat arterial hypertension (high blood pressure) and the treatment of heart failure . Its operating principle is based on the inhibition of the angiotensin converting enzyme (ACE).

chemistry

Lisinopril is a second generation ACE inhibitor. It has a tripeptide structure consisting of the natural α- amino acids ( S ) - proline and ( S ) - lysine and an unnatural homologue of the α-amino acid ( S ) - phenylalanine .

Lisinopril, along with captopril, is one of the two substances from the ACE inhibitor class, whose zinc complexing group acts directly and is not a prodrug ( carboxy group esterified with ethanol ). Compared to enalapril and ramipril , another difference is that the alanine of the tripeptide has been replaced by lysine .

pharmacology

application areas

Lisinopril is used in monotherapy and in double or triple combinations, preferably with diuretics or calcium antagonists, for the therapy of hypertension, and in monotherapy and double combinations with diuretics for the treatment of symptomatic heart failure , with synergistic effects of the substances in combinations . Furthermore, it has been shown to be effective in pure infarction prophylaxis for up to 6 weeks after a heart attack . Due to the nephroprotective properties (kidney protection), use in patients with high blood pressure in diabetes mellitus type II and incipient kidney diseases (e.g. nephropathy ) is possible and indicated.

Mechanism of action

Lisinopril leads as inhibitor of angiotensin converting enzyme in a decreased formation of angiotensin II from angiotensin I . This reduced formation of angiotensin II causes a decrease in the tone of the blood vessels and thus a decrease in blood pressure. The decrease in the angiotensin II level also leads to a reduction in the release of aldosterone from the adrenal cortex and thus to an influence on the water balance (see also renin-angiotensin-aldosterone system ). At the cellular level, a decrease in the mitogenic effects mediated by angiotensin II on cells of the heart, which lead to unfavorable changes (remodeling), especially after a myocardial infarction, can be observed.

Side effects

Most of the side effects of lisinopril have been associated with the slower breakdown and accumulation of bradykinin caused by ACE inhibitors . These include skin reactions such as B. exanthema and hives , also angioedema . Serious allergic skin reactions, however, are only very rarely observed.

Respiratory side effects include dry cough, hoarseness, and sore throat. Asthma attacks and shortness of breath can also occur, albeit rarely.

An excessive decrease in blood pressure may occur as a result of the main action of lisinopril. As a result, dizziness, headache, and drowsiness may occasionally be observed. Serious cardiovascular events such as angina pectoris , myocardial infarction and syncope have only been reported in isolated cases.

Functional kidney dysfunctions can occasionally be observed through interference with the water and electrolyte balance. Proteinuria (excretion of proteins in the urine), however, has only rarely been observed.

Since lisinopril during pregnancy can cause growth and bone formation disorders in the child combined with increased mortality, it must not be taken during this time and should be replaced by other suitable therapeutic measures.

Interactions

Lisinopril increases the blood sugar lowering effect of insulin and oral antidiabetic drugs , as well as the blood count-altering effects of immunosuppressants .

By interfering with the water and electrolyte balance, the elimination of electrolytes can be slowed down, which should be taken into account in particular when treating with lithium and potassium-sparing diuretics .

When combined with other antihypertensive drugs, increased blood pressure lowering should be taken into account.

Potency

Lisinopril is available in the following strengths:

• as a single preparation - 2.5 mg, 5 mg, 10 mg and 20 mg
• in combination with hydrochlorothiazide - 10 / 12.5 mg and 20 / 12.5 mg

Trade names

Monopreparations

Acerbon (D), Acemin (A), Acetan (A), Prinil (CH), Zestril (CH), numerous generics (D, CH)

Combination preparations

Acelisino (A), Acercomp (D, A), Co-Acetan (A), Prinzide (CH), Zestoretic (CH), various generics with the prefix "Co-" and the appendix "comp", "HCT", " mite "or" plus "(D, A, CH)

Individual evidence

1. ↑ External identifiers or database links for lisinopril dihydrate : CAS number: 83915-83-7, EC number: 627-033-9, ECHA InfoCard: 100.155.382 , PubChem : 5362118 , ChemSpider : 4514932 , Wikidata : Q47495698 .
2. ↑ Mary Adele J. O'Neil (ed.) The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th edition. Merck & Co., Inc., Whitehouse Station NJ 2006, ISBN 0-911910-00-X , p. 956.
3. ↑ ^{a b} Lisinopril data sheet from Sigma-Aldrich , accessed on February 25, 2011 ( PDF ).
4. ↑ Ernst Mutschler , Gerd Geisslinger, Heyo K. Kroemer , Peter Ruth, Monika Schäfer-Korting : Mutschler drug effects. Textbook of pharmacology and toxicology. With introductory chapters in anatomy, physiology and pathophysiology. 9th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 2008, ISBN 978-3-8047-1952-1 .
5. ↑ www.Leitlinien.net AWMF Guidelines Register No. 046/001 Development stage: 2 (hypertension).
6. ↑ ^{a b} ABDA database (as of July 15, 2008) of DIMDI .
7. ↑ Red List online, as of October 2009.
8. ↑ AM comp. d. Switzerland, as of October 2009.
9. ↑ AGES-PharmMed, as of October 2009.

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