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2D Structure
Also known as: Prinivil, Zestril, 76547-98-3, Linopril, Lisipril, Lysinopril
Molecular Formula
C21H31N3O5
Molecular Weight
405.5  g/mol
InChI Key
RLAWWYSOJDYHDC-BZSNNMDCSA-N
FDA UNII
7Q3P4BS2FD

One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure.
Lisinopril anhydrous is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of lisinopril anhydrous is as an Angiotensin-converting Enzyme Inhibitor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
2.1.2 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
2.1.3 InChI Key
RLAWWYSOJDYHDC-BZSNNMDCSA-N
2.1.4 Canonical SMILES
C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O
2.1.5 Isomeric SMILES
C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
7Q3P4BS2FD
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Lisinopril Maleate (1:1)

2. Lisinopril Sulfate (1:2)

3. Lysinopril

4. Mk-521

5. Prinivil

6. Zestril

2.3.2 Depositor-Supplied Synonyms

1. Prinivil

2. Zestril

3. 76547-98-3

4. Linopril

5. Lisipril

6. Lysinopril

7. Tensopril

8. 83915-83-7

9. Lisinopril Anhydrous

10. Acercomp

11. Inhibril

12. Noperten

13. Presiten

14. Sinopril

15. Acerbon

16. Carace

17. Vivatec

18. Coric

19. Alapril

20. Inopril

21. Lisinal

22. Lisoril

23. Lispril

24. Novatec

25. Sinopryl

26. Cipral

27. Cipril

28. Linvas

29. Lipril

30. Loril

31. Prinil

32. Tensyn

33. Tersif

34. Lisinoprilum

35. Longes

36. Hipril

37. Mk-521

38. Lisinopril (inn)

39. Lisinopril [inn]

40. [n2-[(s)-1-carboxy-3-phenylpropyl]-l-lysyl-l-proline

41. Lisinopril (zestril)

42. N2-[(1s)-1-carboxy-3-phenylpropyl]-l-lysyl-l-proline

43. Zestril (tn)

44. 7q3p4bs2fd

45. Chebi:43755

46. Qbrelis

47. Nsc-751176

48. Nsc-758151

49. (s)-1-((s)-6-amino-2-(((s)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylic Acid

50. Lpr

51. L-proline, N2-((1s)-1-carboxy-3-phenylpropyl)-l-lysyl-

52. (s)-1-(n2-(1-carboxy-3-phenylpropyl)-l-lysyl)-l-proline

53. Nanopril

54. Lisinoprilum [latin]

55. (s)-1-(n(2)-(1-carboxy-3-phenylpropyl)-l-lysyl)-l-proline

56. Chembl1237

57. (2s)-1-[(2s)-6-amino-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic Acid

58. Lizinopril

59. Diroton

60. Lisitec

61. Lisopril

62. Listril

63. Lizonoton

64. Optimon

65. Prinvil

66. Skopryl

67. Vitopril

68. Amicor

69. Doneka

70. Irumed

71. Laaven

72. Mls002154258

73. Mk 521

74. Mk 522

75. (2s)-1-[(2s)-6-amino-2-{[(1s)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic Acid

76. Smr000544473

77. Ccris 3568

78. Smr001233519

79. Einecs 278-488-1

80. Unii-7q3p4bs2fd

81. Brn 4276619

82. Lysinopryl

83. (s)-1-[n2-(1-carboxy-3-phenylpropyl)-l-lysyl]-l-proline

84. L-proline, N2-[(1s)-1-carboxy-3-phenylpropyl]-l-lysyl-

85. N-(1(s)-carboxy-3-phenylpropyl)-l-lysyl-l-proline

86. N2-((s)-1-carboxy-3-phenylpropyl)-l-lysyl-l-proline

87. Lisiprilprinivil

88. Hsdb 6852

89. (s)-1-(n(sup 2)-(1-carboxy-3-phenylpropyl)-l-lysyl)-l-proline

90. 77726-95-5

91. (s)-1-[n2-(1-carboxy-3-phenylpropyl)-l-lysyl]-l-proline Dihydrate

92. 1-(n2-(1-carboxy-3-phenylpropyl)-l-lysyl)-l-proline

93. Spectrum_000497

94. Lisinopril [mi]

95. Prestwick0_000301

96. Prestwick1_000301

97. Prestwick2_000301

98. Prestwick3_000301

99. Spectrum2_001456

100. Spectrum3_000941

101. Spectrum4_001040

102. Spectrum5_000995

103. (s)-lisinopril Dihydrate

104. Lisinopril [who-dd]

105. Schembl15680

106. Bspbio_000262

107. Kbiogr_001599

108. Kbioss_000977

109. (2s)-1-[(2s)-6-amino-2-[[(2s)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic Acid

110. Mls001306436

111. Mls001306481

112. Bidd:gt0755

113. Divk1c_001037

114. Spectrum1501217

115. Spbio_001351

116. Spbio_002481

117. Bpbio1_000290

118. Gtpl6360

119. Ici-209k

120. Dtxsid6040537

121. Bdbm66979

122. Hms503o15

123. Kbio1_001037

124. Kbio2_000977

125. Kbio2_003545

126. Kbio2_006113

127. Kbio3_002002

128. L-proline, 1-(n2-(1-carboxy-3-phenylpropyl)-l-lysyl)-

129. N(2)-[(1s)-1-carboxy-3-phenylpropyl]-l-lysyl-l-proline

130. N~2~-[(1s)-1-carboxy-3-phenylpropyl]-l-lysyl-l-proline

131. Cid_22887897

132. Ninds_001037

133. Hms1921b14

134. Hms2090o14

135. Hms2092l21

136. Hms2850n20

137. Pharmakon1600-01501217

138. 1-[nalpha-[(s)-1-carboxy-3-phenylpropyl]-l-lysyl]-l-proline

139. L-proline, 1-(n2-(1-carboxy-3-phenylpropyl)-l-lysyl)-, (s)-

140. Zinc3812863

141. Bdbm50367879

142. Ccg-39190

143. Dl-434

144. Nsc751176

145. Nsc758151

146. S2076

147. Akos015836369

148. Akos015894970

149. L-proline, 1-(n(sup 2)-(1-carboxy-3-phenylpropyl)-l-lysyl)-, (s)-

150. Bcp9000856

151. Db00722

152. Idi1_001037

153. Ncgc00179623-01

154. Ncgc00179623-07

155. Hy-18206

156. Sbi-0051692.p002

157. L0220

158. C76449

159. D08131

160. Ab00052250-13

161. Ab00052250_14

162. Ab00052250_15

163. 547l983

164. A838743

165. Q412208

166. Sr-05000001786

167. Sr-05000001786-1

168. Brd-k67966701-335-03-5

169. Z2786051707

170. N-[n2 (1(s)-carboxy-3-phenylpropyl)-l-lysyl]-l-proline

171. N-[n2 -(1(s)-carboxy-3-phenylpropyl)-l-lysyl]-l-proline

172. 1-(n(sup 2)-((s)-1-carboxy-3-phenylpropyl)-l-lysyl)-l-proline

173. L-proline, 1-(n(sup 2)-(1-carboxy-3-phenylpropyl)-l-lysyl)-

174. (2s)-1-[(2s)-6-amino-2-[[(1s)-1-carboxy-3-phenyl-propyl]amino]hexanoyl]proline;hydrate

175. (2s)-1-[(2s)-6-amino-2-[[(1s)-1-carboxy-3-phenyl-propyl]amino]hexanoyl]pyrrolidine-2-carboxylic Acid;lisinopril

176. (2s)-1-[(2s)-6-amino-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]-1-oxohexyl]-2-pyrrolidinecarboxylic Acid;hydrate

177. (2s)-1-[(2s)-6-amino-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic Acid;hydrate

178. (2s)-1-[(2s)-6-azanyl-2-[[(2s)-1-oxidanyl-1-oxidanylidene-4-phenyl-butan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic Acid;hydrate

179. (s)-1-((s)-6-amino-2-((s)-1-carboxy-3-phenylpropylamino)hexanoyl)pyrrolidine-2-carboxylic Acid

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 405.5 g/mol
Molecular Formula C21H31N3O5
XLogP3-2.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count12
Exact Mass405.22637110 g/mol
Monoisotopic Mass405.22637110 g/mol
Topological Polar Surface Area133 Ų
Heavy Atom Count29
Formal Charge0
Complexity550
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameLisinopril
PubMed HealthLisinopril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelLisinopril is an oral long-acting angiotensin converting enzyme inhibitor. Lisinopril, a synthetic peptide derivative, is chemically described as (S)-1-[N2-(1-Carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate. Its empirical formula is C21H31N3O52H...
Active IngredientLisinopril
Dosage FormTablet
RouteOral
Strength2.5mg; 30mg; 5mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyHikma Intl Pharms; Wockhardt; Ranbaxy; Apotex; Accord Hlthcare; Aurobindo; Lupin; Sandoz; Prinston; Invagen Pharms; Watson Labs; Ivax Sub Teva Pharms; Vintage; Mylan

2 of 6  
Drug NamePrinivil
PubMed HealthLisinopril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelPRINIVIL (Lisinopril), a synthetic peptide derivative, is an oral long-acting angiotensin converting enzyme inhibitor. Lisinopril is chemically described as (S)-1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate. Its empirical formula is...
Active IngredientLisinopril
Dosage FormTablet
RouteOral
Strength5mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyMerck

3 of 6  
Drug NameZestril
PubMed HealthLisinopril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelLisinopril is an oral long-acting angiotensin converting enzyme inhibitor. Lisinopril, a synthetic peptide derivative, is chemically described as (S)-1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate. Its empirical formula is C21H31N3O5.2...
Active IngredientLisinopril
Dosage FormTablet
RouteOral
Strength2.5mg; 30mg; 5mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyAstrazeneca

4 of 6  
Drug NameLisinopril
PubMed HealthLisinopril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelLisinopril is an oral long-acting angiotensin converting enzyme inhibitor. Lisinopril, a synthetic peptide derivative, is chemically described as (S)-1-[N2-(1-Carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate. Its empirical formula is C21H31N3O52H...
Active IngredientLisinopril
Dosage FormTablet
RouteOral
Strength2.5mg; 30mg; 5mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyHikma Intl Pharms; Wockhardt; Ranbaxy; Apotex; Accord Hlthcare; Aurobindo; Lupin; Sandoz; Prinston; Invagen Pharms; Watson Labs; Ivax Sub Teva Pharms; Vintage; Mylan

5 of 6  
Drug NamePrinivil
PubMed HealthLisinopril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelPRINIVIL (Lisinopril), a synthetic peptide derivative, is an oral long-acting angiotensin converting enzyme inhibitor. Lisinopril is chemically described as (S)-1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate. Its empirical formula is...
Active IngredientLisinopril
Dosage FormTablet
RouteOral
Strength5mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyMerck

6 of 6  
Drug NameZestril
PubMed HealthLisinopril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelLisinopril is an oral long-acting angiotensin converting enzyme inhibitor. Lisinopril, a synthetic peptide derivative, is chemically described as (S)-1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-L-proline dihydrate. Its empirical formula is C21H31N3O5.2...
Active IngredientLisinopril
Dosage FormTablet
RouteOral
Strength2.5mg; 30mg; 5mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyAstrazeneca

4.2 Therapeutic Uses

Angiotensin-Converting Enzyme Inhibitors; Antihypertensive Agents; Cardiotonic Agents

National Library of Medicine's Medical Subject Headings. Lisinopril. Online file (MeSH, 2016). Available from, as of October 28, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html


Prinivil is indicated for the treatment of hypertension in adult patients and pediatric patients 6 years of age and older to lower blood pressure. Lowering blood pressure lowers the risk of fatal and non-fatal cardiovascular events, primarily strokes and myocardial infarctions. ... Prinivil may be administered alone or with other antihypertensive agents /Included in US product labeling/

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


Prinivil is indicated to reduce signs and symptoms of heart failure in patients who are not responding adequately to diuretics and digitalis /Included in US product labeling/

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


Prinivil is indicated for the reduction of mortality in treatment of hemodynamically stable patients within 24 hours of acute myocardial infarction. Patients should receive, as appropriate, the standard recommended treatments such as thrombolytics, aspirin and beta-blockers. /Included in US product label/

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


For more Therapeutic Uses (Complete) data for LISINOPRIL (6 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ WARNING: FETAL TOXICITY When pregnancy is detected, discontinue Prinivil as soon as possible. Drugs that act directly on the renin-angiotensin system can cause injury and death to the developing fetus.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


Milk of lactating rats contains radioactivity following administration of (14)C lisinopril. It is not known whether this drug is secreted in human milk. Because many drugs are secreted in human milk, and because of the potential for serious adverse reactions in nursing infants from ACE inhibitors, discontinue nursing or discontinue Prinivil.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


Antihypertensive effects and safety of Prinivil have been established in pediatric patients aged 6 to 16 years. No relevant differences between the adverse reaction profile for pediatric patients and adult patients were identified. Safety and effectiveness of Prinivil have not been established in pediatric patients under the age of 6 or in pediatric patients with glomerular filtration rate <30 mL/min/1.73 sq m.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


Adverse effects reported in greater than 1% of patients receiving lisinopril for the management of heart failure and more frequently than with placebo include dizziness, hypotension, headache, diarrhea, chest pain, nausea, abdominal pain, rash, and upper respiratory tract infection.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 2071


For more Drug Warnings (Complete) data for LISINOPRIL (23 total), please visit the HSDB record page.


4.4 Drug Indication

Lisinopril is indicated for the treatment of acute myocardial infarction, hypertension in patients 6 years, and as an adjunct therapy for heart failure. A combination product with hydrochlorothiazide is indicated for the treatment of hypertension.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Lisinopril is an angiotensin converting enzyme inhibitor used to treat hypertension, heart failure, and myocardial infarction. Lisinopril is not a prodrug, and functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system. It has a wide therapeutic index and a long duration of action as patients are generally given 10-80mg daily.


5.2 MeSH Pharmacological Classification

Angiotensin-Converting Enzyme Inhibitors

A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. (See all compounds classified as Angiotensin-Converting Enzyme Inhibitors.)


Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
LISINOPRIL ANHYDROUS
5.3.2 FDA UNII
7Q3P4BS2FD
5.3.3 Pharmacological Classes
Angiotensin-converting Enzyme Inhibitors [MoA]; Angiotensin Converting Enzyme Inhibitor [EPC]
5.4 ATC Code

C09AA03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C09 - Agents acting on the renin-angiotensin system

C09A - Ace inhibitors, plain

C09AA - Ace inhibitors, plain

C09AA03 - Lisinopril


5.5 Absorption, Distribution and Excretion

Absorption

Lisinopril is 6-60% orally bioavailable with an average of 25% bioavailability. Lisinopril reaches a Cmax of 58ng/mL with a Tmax of 6-8h. Lisinopril's absorption is not affected by food.


Route of Elimination

Lisinopril is entirely eliminated exclusively in the urine.


Volume of Distribution

The apparent volume of distribution of lisinopril is 124L.


Clearance

A 30kg child has a typical clearance of 10L/h, which increases with renal function. The mean renal clearance of lisinopril in healthy adult males is 121mL/min.


Steady state is attained after two daily doses (every 24 hours) in healthy volunteers. The drug is not metabolized but is eliminated via the kidneys.

Beermann B; Am J Med 85 (3b): 25-30 (1988)


In dogs, lisinopril's bioavilability ranges from 24-50% with peak levels occurring approximately 4 hours after dosing. Lisinopril is distributed poorly into the CNS. It is unknown if it is distributed into maternal milk, but it does cross the placenta.

Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 857


Following oral administration of Prinivil, peak serum concentrations of lisinopril occur within about 7 hours, although there was a trend to a small delay in time taken to reach peak serum concentrations in acute myocardial infarction patients. Declining serum concentrations exhibit a prolonged terminal phase which does not contribute to drug accumulation. This terminal phase probably represents saturable binding to ACE and is not proportional to dose.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


Lisinopril does not appear to be bound to other serum proteins. Lisinopril does not undergo metabolism and is excreted unchanged entirely in the urine. Based on urinary recovery, the mean extent of absorption of lisinopril is approximately 25 percent, with large inter-subject variability (6-60 percent) at all doses tested (5-80 mg). Lisinopril absorption is not influenced by the presence of food in the gastrointestinal tract. The absolute bioavailability of lisinopril is reduced to about 16 percent in patients with stable NYHA Class II-IV congestive heart failure, and the volume of distribution appears to be slightly smaller than that in normal subjects. The oral bioavailability of lisinopril in patients with acute myocardial infarction is similar to that in healthy volunteers.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


For more Absorption, Distribution and Excretion (Complete) data for LISINOPRIL (9 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Lisinopril is not metabolized and is excreted as the unchanged drug.


Lisinopril does not undergo metabolism and is excreted unchanged entirely in the urine.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


5.7 Biological Half-Life

Lisinopril has an effective half life of accumulation of 12.6h and a terminal half life of 46.7h.


The plasma half-life controlling accumulation during chronic administration is 12-13 hr and the absorbed drug is eliminated via glomerular filtration.

PMID:2550635 Case DE et al; J Hum Hypertens 3 (Suppl 1): 127-31 (1989)


The accumulation half-life averages 12.6 hours despite a terminal serum half-life of approximately 40 hours /in healthy volunteers/.

Beermann B; AmJ Med 85 (3b): 25-30 (1988)


Upon multiple dosing, lisinopril exhibits an effective half-life of 12 hours.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


5.8 Mechanism of Action

Angiotensin II constricts coronary blood vessels and is positively inotropic, which under normal circumstances, would increase vascular resistance and oxygen consumption. This action can eventually lead to myocyte hypertrophy and vascular smooth muscle cell proliferation. Lisinopril is an angiotensin converting enzyme inhibitor (ACEI), preventing the conversion of angiotensin I to angiotensin II. This action prevents myocyte hypertrophy and vascular smooth muscle cell proliferation seen in untreated patients. Increased levels of bradykinin also exhibit vasodilating effects for patients taking ACEIs. Lisinopril also inhibits renin's conversion of angiotensin to angiotensin I.


Orally active angiotensin-converting enzyme inhibitor.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1026


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. The latter decrease may result in a small increase of serum potassium.

NIH; DailyMed. Current Medication Information for Prinivil (Lisinopril) Tablet (Updated: October 2016). Available from, as of October 31, 2016: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6f3c339-2c9d-4d07-14a1-6d6c7daf26c6


The action of the angiotensin-converting enzyme (ACE) inhibitor lisinopril on the consequences of myocardial reoxygenation and oxidative damage was assessed in cultured chick embryonic ventricular cardiomyocytes. Lisinopril, 10(-8) M to 10(-6) M, produced a significant (P < 0.05) dose-dependent enhancement of the restoration of contractile frequency occurring during myocardial reoxygenation but did not alter the depression in contractile frequency during hypoxia. Lisinopril significantly (P < 0.05) shifted the dose-response relationship of ammonium persulfate-induced reduction in cardiac contractile frequency. Lisinopril significantly (P < 0.05) reduced the effect of another oxidative agent, tertbutylhydroperoxide which produced a time-dependent reduction in cardiac contractile frequency. Lisinopril did not alter cardiac contractile frequency in the absence of hypoxia or ammonium persulfate or tertbutylhydroperoxide. The viability of cardiomyocytes, assessed by trypan blue exclusion, paralleled the changes in cardiac contractile frequency. Lisinopril significantly (P < 0.05) improved viability of cardiomyocytes exposed to either ammonium persulfate or tertbutylhydroperoxide. Lisinopril did not display any antioxidant properties against the free radical alpha,alpha-diphenyl-beta-picrylhydrazyl. These data suggest that lisinopril accelerates the recovery of cardiomyocytes during reoxygenation and blunts the effects of oxidative agents through mechanisms involving the endogenous renin angiotensin system and/or a direct cellular action.

PMID:8405086 Rabkin; Eur J Pharmacol 238 (1): 81-88 (1993)