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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H31N3O5
Molecular Weight 405.4879
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LISINOPRIL ANHYDROUS

SMILES

NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N2CCC[C@H]2C(O)=O

InChI

InChIKey=RLAWWYSOJDYHDC-BZSNNMDCSA-N
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

HIDE SMILES / InChI

Description

Lisinopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE). Lisinopril is marketed under the brand name ZESTRIL. ZESTRIL is indicated for the treatment of hypertension. It may be used alone as initial therapy or concomitantly with other classes of antihypertensive agents. It is also indicated as adjunctive therapy in the management of heart failure in patients who are not responding adequately to diuretics and digitalis. Lisinopril inhibits angiotensin-converting enzyme (ACE) in human subjects and animals. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex. The beneficial effects of lisinopril in hypertension and heart failure appear to result primarily from suppression of the renin-angiotensin-aldosterone system. Inhibition of ACE results in decreased plasma angiotensin II which leads to decreased vasopressor activity and to decreased aldosterone secretion. While the mechanism through which ZESTRIL lowers blood pressure is believed to be primarily suppression of the renin-angiotensin-aldosterone system, ZESTRIL is antihypertensive even in patients with low-renin hypertension.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.36 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
[Antihypertensive effect of enalapril and lisinopril administered in combination with nonsteroid anti-inflammatory agents].
2001
Telmisartan: a review of its use in hypertension.
2001
Effects of lisinopril on streptozotocin-induced diabetic neuropathy in rats.
2001 Apr
Angiotensin-converting enzyme degrades Alzheimer amyloid beta-peptide (A beta ); retards A beta aggregation, deposition, fibril formation; and inhibits cytotoxicity.
2001 Dec 21
Fluorescence polarization studies of different forms of angiotensin-converting enzyme.
2001 Jul
Simultaneous determination of hydrochlorothiazide and several inhibitors of angiotensin-converting enzyme by capillary electrophoresis.
2001 Jul 27
Prescribing patterns and cost of antihypertensive drugs in an internal medicine clinic.
2001 May-Jun
Pet ownership, but not ace inhibitor therapy, blunts home blood pressure responses to mental stress.
2001 Oct
Differential manipulation of the renin angiotensin system and epoietin requirements in maintenance haemodialysis patients.
2001 Sep
Angiotensin-converting enzyme inhibition induces apoptosis in erythroid precursors and affects insulin-like growth factor-1 in posttransplantation erythrocytosis.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Hypertension Initial dose: 10 mg orally once a day; 5 mg orally once a day Maintenance dose: 20 to 40 mg orally once a day Maximum dose: 80 mg orally once a day Usual Adult Dose for Congestive Heart Failure Initial dose: 2.5 to 5 mg orally once a day Maintenance dose: Dosage should be increased as tolerated Maximum dose: 40 mg orally once a day Usual Adult Dose for Myocardial Infarction Initial dose: 5 mg orally (within 24 hours of the onset of acute myocardial infarction) Subsequent doses: 5 mg orally after 24 hours, then 10 mg orally after 48 hours. Maintenance dose: 10 mg orally once a day. Dosing should continue for at least 6 weeks.
Route of Administration: Oral
In Vitro Use Guide
Lisinopril inhibited angiotensin converting enzyme from sheep serum with IC50 5.6 nM
Name Type Language
LISINOPRIL ANHYDROUS
Common Name English
LISINOPRIL [INN]
Common Name English
L-PROLINE, 1-(N(SUP 2)-(1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-
Common Name English
LISINOPRIL [WHO-DD]
Common Name English
1-(N(SUP 2)-((S)-1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-L-PROLINE
Systematic Name English
LISINOPRIL [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000181
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
WHO-ATC C09AA03
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
NDF-RT N0000175562
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
Code System Code Type Description
HSDB
76547-98-3
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY
EVMPD
SUB08533MIG
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY
EVMPD
SUB23348
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY
PUBCHEM
5362119
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY SWITZERF
MERCK INDEX
M6842
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY Merck Index
ECHA (EC/EINECS)
278-488-1
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY
RXCUI
1546022
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY RxNorm
CAS
76547-98-3
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY
EPA CompTox
76547-98-3
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY
NCI_THESAURUS
C83924
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY
INN
5425
Created by admin on Tue Mar 06 12:31:07 UTC 2018 , Edited by admin on Tue Mar 06 12:31:07 UTC 2018
PRIMARY