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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H31N3O5.2H2O
Molecular Weight 441.5185
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LISINOPRIL

SMILES

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

InChI

InChIKey=CZRQXSDBMCMPNJ-ZUIPZQNBSA-N
InChI=1S/C21H31N3O5.2H2O/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);2*1H2/t16-,17-,18-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H31N3O5
Molecular Weight 405.4879
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Primary TargetPharmacologyConditionPotency
0.36 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZESTRIL
Primary
ZESTRIL
Primary
ZESTRIL

PubMed

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
Substance Class Chemical
Record UNII
E7199S1YWR
Record Status Validated (UNII)
Record Version