Lisinopril

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Cat Number

API0232182

CAS Number

76547-98-3

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Product Detail Description Scientific Support Customer Q&A

CAS Number

76547-98-3

EINECS

278-488-1

Storage

Store at room temperature

Synonyms

Prinivil; Zestril; Lisinopril anhydrous; Lysinopril; Carace; Novatec; Lisinoprilum

Molecular Formula

C21H31N3O5

Molecular Weight

405.5

Smiles

C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O

Appearance

White to off-white solid powder

Melting Point

162-165°C

Boiling Point

666.4±55.0°C (Predicted)

Relative Density

1.251±0.06 (Predicted)

General Description

Lisinopril is a lysine-containing dicarboxylate angiotensin-converting enzyme (ACE) inhibitor, the active diacid derivative of enalaprilat. Its structure is a lysine analogue of enalaprilat, containing a proline ring and a lysine group, which is responsible for its water solubility. Lisinopril is a white to off-white crystalline powder with a molecular weight of 441.5 Da (as the dihydrate).

Mechanism of Action

Lisinopril competitively inhibits ACE (kininase II), preventing the conversion of angiotensin I to the potent vasoconstrictor angiotensin II. This reduces angiotensin II-mediated vasoconstriction, aldosterone secretion, and sympathetic activation. The drug also blocks the breakdown of bradykinin, leading to increased bradykinin levels, which contributes to its vasodilatory effects but also causes a dry cough.

Application

Lisinopril is indicated for the treatment of hypertension, heart failure, and acute myocardial infarction (to improve survival and reduce ventricular dysfunction). It also slows the progression of diabetic nephropathy in patients with type 2 diabetes and hypertension.

This systematic review of off-label lisinopril uses found strong evidence for efficacy in proteinuric kidney disease, though with a slight GFR reduction. Positive effects were also reported for diabetic nephropathy, migraine, diabetes prevention, myocardial fibrosis, mitral regurgitation, Duchenne cardiomyopathy, oligospermia/infertility, and diabetic retinopathy.

Fig. 1 PRISMA flow diagram summarizing retrieved, included, and excluded randomized controlled trials. (Sadat-Ebrahimi SR, et al., 2018)

References

Sadat-Ebrahimi SR, et al. An evidence-based systematic review of the off-label uses of lisinopril. Br J Clin Pharmacol. 2018;84(11):2502-2521.

Does Lisinopril require protection from moisture during storage?

Yes, it is hygroscopic. The lysine side chain can absorb moisture, leading to hydrolysis and formation of the diketopiperazine impurity. Store in tightly sealed containers with desiccant.