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Chemistry

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Also known as: 87333-19-5, Tritace, Altace, Ramace, Triatec, Delix
Molecular Formula
C23H32N2O5
Molecular Weight
416.5  g/mol
InChI Key
HDACQVRGBOVJII-JBDAPHQKSA-N
FDA UNII
L35JN3I7SJ

Ramipril
A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.
Ramipril is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of ramipril is as an Angiotensin-converting Enzyme Inhibitor.
1 2D Structure

Ramipril

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
2.1.2 InChI
InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1
2.1.3 InChI Key
HDACQVRGBOVJII-JBDAPHQKSA-N
2.1.4 Canonical SMILES
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C3CCCC3CC2C(=O)O
2.1.5 Isomeric SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@H]3CCC[C@H]3C[C@H]2C(=O)O
2.2 Other Identifiers
2.2.1 UNII
L35JN3I7SJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acovil

2. Altace

3. Carasel

4. Delix

5. Hoe 498

6. Hoe-498

7. Hoe498

8. Ramace

9. Triatec

10. Tritace

11. Vesdil

12. Zabien

2.3.2 Depositor-Supplied Synonyms

1. 87333-19-5

2. Tritace

3. Altace

4. Ramace

5. Triatec

6. Delix

7. Carasel

8. Vesdil

9. Cardace

10. Hoe-498

11. Pramace

12. Ramiprilum [latin]

13. Ramiprilum

14. Unipril

15. Hoe 498

16. Quark

17. Altace (tn)

18. Corpril

19. Ramipres

20. Ecator

21. Hopace

22. Acovil

23. C09aa05

24. Lostapres

25. Hytren

26. (2s,3as,6as)-1-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]pyrrole-2-carboxylic Acid

27. Nsc-758933

28. Chembl1168

29. L35jn3i7sj

30. Chebi:8774

31. (2s,3as,6as)-1-((s)-n-((s)-1-carboxy-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrole-2-carboxylic Acid, 1-ethyl Ester

32. Ramipro

33. Naprix

34. Mfcd00865775

35. Dsstox_cid_3551

36. Dsstox_rid_77077

37. Dsstox_gsid_23551

38. (2s,3as,6as)-1-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-l-alanyl)octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

39. (2s,3as,6as)-1-((s)-2-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

40. (2s,3as,6as)-1-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azaniumyl]propanoyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]pyrrole-2-carboxylate

41. (2s,3as,6as)-1-[(2s)-2-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

42. (2s-(1(r*(r*)),2alpha,3abeta,6abeta))-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic Acid

43. Hoe498

44. Ramipril (altace)

45. (2s,3as,6as)-1-[(2s)-2-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid (non-preferred Name)

46. Cyclopenta[b]pyrrole-2-carboxylic Acid, 1-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydro-, (2s,3as,6as)-

47. Smr000466386

48. Ramipril (usp/inn)

49. Sr-05000001908

50. Unii-l35jn3i7sj

51. Ramipril [usan:usp:inn:ban]

52. Ncgc00016955-01

53. Cyclopenta(b)pyrrole-2-carboxylic Acid, 1-((2s)-2-(((1s)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-, (2s,3as,6as)-

54. Cas-87333-19-5

55. (2s,3as,6as)-1-((s)-n-((s)-1-ethoxycarbonyl-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrol-2-carbonsaeure

56. Spectrum_001958

57. Ramipril [usan]

58. Ramipril [inn]

59. Ramipril [jan]

60. Ramipril [mi]

61. Ramipril [vandf]

62. Spectrum3_001794

63. Spectrum4_001269

64. Spectrum5_001721

65. Ramipril [mart.]

66. Ramipril [usp-rs]

67. Ramipril [who-dd]

68. Schembl16059

69. Bspbio_003347

70. Kbiogr_001858

71. Kbioss_002512

72. Ramipril, (+)-

73. Cyclopenta(b)pyrrole-2-carboxylic Acid, 1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-, (2s-(1(r*(r*)),2alpha,3abeta,6abeta))-

74. Mls000759523

75. Mls001216547

76. Mls001423965

77. N-(1s-carboethoxy-3-phenylpropyl)-s-alanyl-cis,endo-2-azabicyclo[3.3.0]octane-3s-carboxylic Acid

78. Bidd:gt0803

79. Spectrum1505214

80. Ramipril [orange Book]

81. Gtpl6339

82. Ramipril [ep Monograph]

83. Ramipril, >=98% (hplc)

84. Dtxsid8023551

85. Ramipril [usp Monograph]

86. Hsdb 8393

87. Kbio2_002504

88. Kbio2_005072

89. Kbio2_007640

90. Kbio3_002849

91. Polycap Component Ramipril

92. Npd2431

93. Hms2051e04

94. Hms2090l11

95. Hms2093m10

96. Hms2231m05

97. Hms3259j07

98. Hms3715m16

99. Pharmakon1600-01505214

100. Cyclopenta(b)pyrrole-2-carboxylic Acid, 1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-, (2s-(1(r*(r*)),2.alpha.,3a.beta.,6a.beta.))-

101. Hy-b0279

102. Zinc3798757

103. Tox21_110708

104. Bbl033964

105. Bdbm50084681

106. Nsc758933

107. S1793

108. Stk801937

109. Akos005622534

110. Tox21_110708_1

111. Ac-1347

112. Ccg-100833

113. Db00178

114. Ks-1103

115. Nc00083

116. Nc00627

117. Nsc 758933

118. Ncgc00178127-01

119. Ncgc00178127-02

120. (2s,3as,6as)-1((s)-n-((s)-1-carboxy-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrole-2-carboxylic

121. (2s,3as,6as)-1-((s)-2-((s)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)propanoyl) Octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

122. (2s,3as,6as)-1-((s)-2-((s)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)propanoyl)-octahydrocyclopenta[b]p

123. (2s,3as,6as)-1-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydro-cyclopenta[b]pyrrole-2-carboxylic Acid

124. (2s,3as,6as)-1-[(2s)-2-{[(1s)-1-ethoxycarbonyl-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

125. (2s,3as,6as)-1-[(s)-2-((s)-1-ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-cyclopenta[b]

126. [2s,3as,6as]-1-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopen

127. Br164319

128. Sbi-0206728.p001

129. B2208

130. R0219

131. D00421

132. Ab00698339-07

133. Ab00698339-08

134. Ab00698339_09

135. Ab00698339_10

136. 333r195

137. Q412666

138. Sr-05000001908-1

139. Sr-05000001908-2

140. Ramipril, British Pharmacopoeia (bp) Reference Standard

141. Ramipril, European Pharmacopoeia (ep) Reference Standard

142. Z1946144927

143. Ramipril, United States Pharmacopeia (usp) Reference Standard

144. Ramipril, Pharmaceutical Secondary Standard; Certified Reference Material

145. (2s,3as,6as)-1-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

146. (2s,3as,6as)-1-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[d]pyrrole-2-carboxylic Acid

147. 1-[2-(1-ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-cyclopenta[b]pyrrole-2-carboxylic Acid(ramipril)

148. 1-[2-(1-ethoxycarbonyl-3-phenylpropylamino)propionyl]octahydrocyclopenta[b]- Pyrrole-2-carboxylic Acid

149. 1028843-43-7

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 416.5 g/mol
Molecular Formula C23H32N2O5
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count10
Exact Mass416.23112213 g/mol
Monoisotopic Mass416.23112213 g/mol
Topological Polar Surface Area95.9 Ų
Heavy Atom Count30
Formal Charge0
Complexity619
Isotope Atom Count0
Defined Atom Stereocenter Count5
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 4  
Drug NameAltace
PubMed HealthRamipril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelRamipril is a 2-aza-bicyclo [3.3.0]-octane-3-carboxylic acid derivative. It is a white, crystalline substance soluble in polar organic solvents and buffered aqueous solutions. Ramipril melts between 105112C.The CAS Registry Number is 87333-19-...
Active IngredientRamipril
Dosage FormCapsule
RouteOral
Strength2.5mg; 5mg; 1.25mg; 10mg
Market StatusPrescription
CompanyKing Pharms

2 of 4  
Drug NameRamipril
PubMed HealthRamipril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelRamipril is a 2-aza-bicyclo [3.3.0]-octane-3-carboxylic acid derivative. It is a white, crystalline substance soluble in polar organic solvents and buffered aqueous solutions. Ramipril melts between 105and 112Ramipril's chemical name is (2S,3aS,6aS)-
Active IngredientRamipril
Dosage FormTablet; Capsule
RouteOral
Strength2.5mg; 1.25mg; 5mg; 10mg
Market StatusPrescription
CompanyMylan Pharms; Apotex; Accord Hlthcare; Aurobindo Pharma; Lupin; Sandoz; Invagen Pharms; Roxane; Watson Labs; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs

3 of 4  
Drug NameAltace
PubMed HealthRamipril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelRamipril is a 2-aza-bicyclo [3.3.0]-octane-3-carboxylic acid derivative. It is a white, crystalline substance soluble in polar organic solvents and buffered aqueous solutions. Ramipril melts between 105112C.The CAS Registry Number is 87333-19-...
Active IngredientRamipril
Dosage FormCapsule
RouteOral
Strength2.5mg; 5mg; 1.25mg; 10mg
Market StatusPrescription
CompanyKing Pharms

4 of 4  
Drug NameRamipril
PubMed HealthRamipril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelRamipril is a 2-aza-bicyclo [3.3.0]-octane-3-carboxylic acid derivative. It is a white, crystalline substance soluble in polar organic solvents and buffered aqueous solutions. Ramipril melts between 105and 112Ramipril's chemical name is (2S,3aS,6aS)-
Active IngredientRamipril
Dosage FormTablet; Capsule
RouteOral
Strength2.5mg; 1.25mg; 5mg; 10mg
Market StatusPrescription
CompanyMylan Pharms; Apotex; Accord Hlthcare; Aurobindo Pharma; Lupin; Sandoz; Invagen Pharms; Roxane; Watson Labs; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs

4.2 Therapeutic Uses

Angiotensin-Converting Enzyme Inhibitors; Antihypertensive Agents

National Library of Medicine's Medical Subject Headings. Ramipril. Online file (MeSH, 2017). Available from, as of Oct 4, 2017: https://meshb.nlm.nih.gov/search


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Ramipril is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of August 30, 2017: https://clinicaltrials.gov/


Ramipril capsules are indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. These benefits have been seen in controlled trials of antihypertensive drugs from a wide variety of pharmacologic classes including this drug. ... Ramipril capsules may be used alone or in combination with thiazide diuretics. /Included in US product label/

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


Ramipril capsules are indicated in stable patients who have demonstrated clinical signs of congestive heart failure within the first few days after sustaining acute myocardial infarction. Administration of ramipril capsules to such patients have been shown to decrease the risk of death (principally cardiovascular death) and to decrease the risks of failure-related hospitalization and progression to severe/resistant heart failure. /Included in US product label/

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


For more Therapeutic Uses (Complete) data for Ramipril (8 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ When pregnancy is detected, discontinue ramipril 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 Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


Use of drugs that act on the renin-angiotensin system during the second and third trimesters of pregnancy reduces fetal renal function and increases fetal and neonatal morbidity and death. Resulting oligohydramnios can be associated with fetal lung hypoplasia and skeletal deformations. Potential neonatal adverse effects include skull hypoplasia, anuria, hypotension, renal failure, and death. When pregnancy is detected, discontinue ramipril as soon as possible. These adverse outcomes are usually associated with use of these drugs in the second and third trimester of pregnancy. Most epidemiologic studies examining fetal abnormalities after exposure to antihypertensive use in the first trimester have not distinguished drugs affecting the renin-angiotensin system from other antihypertensive agents. Appropriate management of maternal hypertension during pregnancy is important to optimize outcomes for both mother and fetus.

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


Angiotensin-converting enzyme (ACE) inhibitors can cause fetal and neonatal morbidity and mortality when used in pregnancy during the second and third trimesters. ACE inhibitors also increase the risk of major congenital malformations when administered during the first trimester of pregnancy. Discontinue as soon as possible when pregnancy is detected, unless continued use is considered lifesaving. Nearly all women can be transferred successfully to alternative therapy for the remainder of their pregnancy. /Angiotensin-converting enzyme (ACE) inhibitors/

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2097


Rare angiotensin-converting enzyme (ACE) inhibitor-associated clinical syndrome manifested initially by cholestatic jaundice may occur; may progress to fulminant hepatic necrosis and is potentially fatal. Patients receiving an ACE inhibitor, including ramipril, who develop jaundice or marked elevations in hepatic enzymes should discontinue the drug and receive appropriate monitoring.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2097


For more Drug Warnings (Complete) data for Ramipril (18 total), please visit the HSDB record page.


4.4 Drug Indication

For the management of mild to severe hypertension. May be used to reduce cardiovascular mortality following myocardial infarction in hemodynamically stable individuals who develop clinical signs of congestive heart failure within a few days following myocardial infarction. To reduce the rate of death, myocardial infarction and stroke in individuals at high risk of cardiovascular events. May be used to slow the progression of renal disease in individuals with hypertension, diabetes mellitus and microalubinuria or overt nephropathy.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ramipril is an ACE inhibitor similar to benazepril, fosinopril and quinapril. It is an inactive prodrug that is converted to ramiprilat in the liver, the main site of activation, and kidneys. Ramiprilat confers blood pressure lowing effects by antagonizing the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may sustain the effects of ramiprilat by causing increased vasodilation and decreased blood pressure.


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
RAMIPRIL
5.3.2 FDA UNII
L35JN3I7SJ
5.3.3 Pharmacological Classes
Angiotensin-converting Enzyme Inhibitors [MoA]; Angiotensin Converting Enzyme Inhibitor [EPC]
5.4 ATC Code

C09AA05

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

C09AA05 - Ramipril


5.5 Absorption, Distribution and Excretion

Absorption

The extent of absorption is at least 50-60%.. Food decreases the rate of absorption from the GI tract without affecting the extent of absorption. The absolute bioavailabilities of ramipril and ramiprilat were 28% and 44%, respectively, when oral administration was compared to intravenous administration. The serum concentration of ramiprilat was unchanged when capsules were opened and the contents dissolved in water, dissolved in apple juice, or suspended in apple sauce.


Route of Elimination

Following oral administration, about 60% of the dose is eliminated in the urine as unchanged ramipril (<2%) and its metabolites. About 40% of the dose is found in the feces, representing both unabsorbed drug and drugs and metabolites eliminated via biliary excretion. The urinary excretion of ramipril may be reduced in patients with impaired renal function.


Clearance

The renal clearance of ramipril and ramiprilat was reported to be 7.2 and 77.4 mL/min/1.73m2. The mean renal clearance of ramipril and ramiprilat is reported to be 10.7 and 126.8 mL/min in healthy elderly patients with normal renal function, additionally the Cmax of ramiprilat is approximately 20% higher in this population. While the pharmacokinetics of ramipril appear unaffected by reduced renal function, the plasma concentration and half-life of ramiprilat are increased. In patient's with hepatic failure the concentration of ramipril is initially increased while the tmax of ramiprilat is prolonged due to a reduced ability to metabolize the drug. However, steady state concentrations of ramiprilat are the same in hepatic failure as in healthy patients.


/MILK/ Ingestion of a single 10 mg oral dose of ramipril resulted in undetectable amounts of ramipril and its metabolites in breast milk.

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


Following oral administration of ramipril, peak plasma concentrations (Cmax) of ramipril are reached within 1 hour. The extent of absorption is at least 50% to 60%, and is not significantly influenced by the presence of food in the gastrointestinal tract, although the rate of absorption is reduced.

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


Plasma concentrations of ramiprilat decline in a triphasic manner (initial rapid decline, apparent elimination phase, terminal elimination phase). The initial rapid decline, which represents distribution of the drug into a large peripheral compartment and subsequent binding to both plasma and tissue ACE, has a half-life of 2 to 4 hours. Because of its potent binding to ACE and slow dissociation from the enzyme, ramiprilat shows two elimination phases. The apparent elimination phase corresponds to the clearance of free ramiprilat and has a half-life of 9 to 18 hours. The terminal elimination phase has a prolonged half-life (>50 hours) and probably represents the binding/dissociation kinetics of the ramiprilat/ACE complex. It does not contribute to the accumulation of the drug. After multiple daily doses of ramipril 5 mg to 10 mg, the half-life of ramiprilat concentrations within the therapeutic range was 13 to 17 hours. /Ramiprilat/

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


Plasma concentrations of ramipril and ramiprilat increase with increased dose, but are not strictly dose-proportional. The 24-hour AUC for ramiprilat, however, is dose-proportional over the 2.5 mg to 20 mg dose range. The absolute bioavailabilities of ramipril and ramiprilat were 28% and 44%, respectively, when 5 mg of oral ramipril was compared with the same dose of ramipril given intravenously.

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


For more Absorption, Distribution and Excretion (Complete) data for Ramipril (7 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic metabolism accounts for 75% of total ramipril metabolism. 25% of hepatic metabolism produces the active metabolite ramiprilat via liver esterase enzymes. 100% of renal metabolism converts ramipril to ramiprilat. Other metabolites, diketopiperazine ester, the diketopiperazine acid, and the glucuronides of ramipril and ramiprilat, are inactive.


Cleavage of the ester group (primarily in the liver) converts ramipril to its active diacid metabolite, ramiprilat. Peak plasma concentrations of ramiprilat are reached 2 to 4 hours after drug intake. The serum protein binding of ramipril is about 73% and that of ramiprilat about 56%; in vitro, these percentages are independent of concentration over the range of 0.01 ug/mL to 10 mcg/mL.

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


After oral administration to dogs, ramipril is rapidly converted via de-esterification into ramiprilat. Bioavailability of ramiprilat after a dose of 0.25 mg/kg per day of ramipril is approximately 6.7%.

Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 1263


Ramipril is a prodrug and has little pharmacologic activity until hydrolyzed in the liver to ramiprilat.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2098


Ramipril is almost completely metabolized to ramiprilat, which has about 6 times the angiotensin-converting enzyme (ACE) inhibitory activity of ramipril, and to the diketopiperazine ester, the diketopiperazine acid, and the glucuronides of ramipril and ramiprilat, all of which are inactive.

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


5.7 Biological Half-Life

Plasma concentrations of ramiprilat decline in a triphasic manner. Initial rapid decline represents distribution into tissues and has a half life of 2-4 hours. The half life of the apparent elimination phase is 9-18 hours, which is thought to represent clearance of free drug. The half-life of the terminal elimination phase is > 50 hours and thought to represent clearance of drug bound to ACE due to its slow dissociation. The half life of ramiprilat after multiple daily doses (MDDs) is dose-dependent, ranging from 13-17 hours with 5-10 mg MDDs to 27-36 hours for 2.5 mg MDDs.


Plasma concentrations of ramiprilat /metabolite of ramipril/ decline in a triphasic manner (initial rapid decline, apparent elimination phase, terminal elimination phase). The initial rapid decline, which represents distribution of the drug into a large peripheral compartment and subsequent binding to both plasma and tissue ACE, has a half-life of 2 to 4 hours. Because of its potent binding to ACE and slow dissociation from the enzyme, ramiprilat shows two elimination phases. The apparent elimination phase corresponds to the clearance of free ramiprilat and has a half-life of 9 to 18 hours. The terminal elimination phase has a prolonged half-life (>50 hours) and probably represents the binding/dissociation kinetics of the ramiprilat/ACE complex. It does not contribute to the accumulation of the drug. After multiple daily doses of ramipril 5 mg to 10 mg, the half-life of ramiprilat concentrations within the therapeutic range was 13 to 17 hours. /Ramiprilat/

NIH; DailyMed. Current Medication Information for Ramipril Capsule (Updated: June 2017). Available from, as of October 25, 2017: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6d57158-e8f9-4c91-8317-0374e0c87d33


5.8 Mechanism of Action

Ramipril inhibits the RAAS system by binding to and inhibiting ACE thereby preventing the conversion of angiotensin I to angiotensin II. As plasma levels of angiotensin II fall, less activation of the G-protein coupled receptors angiotensin receptor I (AT1R) and angiotensin receptor II (AT2R) occurs. AT1R mediates vasoconstriction, inflammation, fibrosis, and oxidative stress through a variety of signaling pathways. These include Gq coupling to the inositol triphosphate pathway, activation of phospholipases C, A2, and D which contribute to eicosanoid production, activation of Ca2+-dependent and MAP kinases, Gi and G12/13, and eventual activation of the Jak/STAT pathway leading to cell growth and production of extracellular matrix components. AT1R activation also leads to increased activity of membrane-bound NADH/NADPH oxidase which contributes to production of reactive oxygen species. Decreased activation of this receptor mediates the renoprotective, antihypertensive, and cardioprotective effects of ramipril by reducing inflammation and vasoconstriction. AT2R acts in opposition to the effects of AT1R by activating phosphotyrosine phosphatases which inhibit MAP kinases, inhibiting Ca2+ channel opening, and stimulating cGMP and nitric oxide production leading to vasodilation. These counteracting effects are shared by the Mas receptor which is activated by Ang(1-7), a subtype of angiotensin produced by plasma esterases from AngI or by ACE2 from AngII produced through a secondary pathway by tonin and cathepsin G. Ang(1-7) also activates AT2R although the bulk of its effect is mediated by MasR. ACE is also responsible for the breakdown of bradykinin. The resulting buildup of bradykinin due to ACE inhibition is thought to mediate the characteristic dry-cough as a side effect of ACE inhibitor medications.


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03-Jan-2022
29-Apr-2025
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DOSAGE - CAPSULE;ORAL - 1.25MG

USFDA APPLICATION NUMBER - 19901

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DOSAGE - CAPSULE;ORAL - 10MG

USFDA APPLICATION NUMBER - 19901

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DOSAGE - CAPSULE;ORAL - 2.5MG

USFDA APPLICATION NUMBER - 19901

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DOSAGE - CAPSULE;ORAL - 5MG

USFDA APPLICATION NUMBER - 19901

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ABOUT THIS PAGE

Looking for 87333-19-5 / Ramipril API manufacturers, exporters & distributors?

Ramipril manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Ramipril API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Ramipril manufacturer or Ramipril supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Ramipril manufacturer or Ramipril supplier.

PharmaCompass also assists you with knowing the Ramipril API Price utilized in the formulation of products. Ramipril API Price is not always fixed or binding as the Ramipril Price is obtained through a variety of data sources. The Ramipril Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Ramipril

Synonyms

87333-19-5, Tritace, Altace, Ramace, Triatec, Delix

Cas Number

87333-19-5

Unique Ingredient Identifier (UNII)

L35JN3I7SJ

About Ramipril

A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.

Naprix Manufacturers

A Naprix manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Naprix, including repackagers and relabelers. The FDA regulates Naprix manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Naprix API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Naprix manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Naprix Suppliers

A Naprix supplier is an individual or a company that provides Naprix active pharmaceutical ingredient (API) or Naprix finished formulations upon request. The Naprix suppliers may include Naprix API manufacturers, exporters, distributors and traders.

click here to find a list of Naprix suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Naprix USDMF

A Naprix DMF (Drug Master File) is a document detailing the whole manufacturing process of Naprix active pharmaceutical ingredient (API) in detail. Different forms of Naprix DMFs exist exist since differing nations have different regulations, such as Naprix USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Naprix DMF submitted to regulatory agencies in the US is known as a USDMF. Naprix USDMF includes data on Naprix's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Naprix USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Naprix suppliers with USDMF on PharmaCompass.

Naprix KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Naprix Drug Master File in Korea (Naprix KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Naprix. The MFDS reviews the Naprix KDMF as part of the drug registration process and uses the information provided in the Naprix KDMF to evaluate the safety and efficacy of the drug.

After submitting a Naprix KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Naprix API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Naprix suppliers with KDMF on PharmaCompass.

Naprix CEP

A Naprix CEP of the European Pharmacopoeia monograph is often referred to as a Naprix Certificate of Suitability (COS). The purpose of a Naprix CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Naprix EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Naprix to their clients by showing that a Naprix CEP has been issued for it. The manufacturer submits a Naprix CEP (COS) as part of the market authorization procedure, and it takes on the role of a Naprix CEP holder for the record. Additionally, the data presented in the Naprix CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Naprix DMF.

A Naprix CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Naprix CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Naprix suppliers with CEP (COS) on PharmaCompass.

Naprix WC

A Naprix written confirmation (Naprix WC) is an official document issued by a regulatory agency to a Naprix manufacturer, verifying that the manufacturing facility of a Naprix active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Naprix APIs or Naprix finished pharmaceutical products to another nation, regulatory agencies frequently require a Naprix WC (written confirmation) as part of the regulatory process.

click here to find a list of Naprix suppliers with Written Confirmation (WC) on PharmaCompass.

Naprix NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Naprix as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Naprix API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Naprix as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Naprix and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Naprix NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Naprix suppliers with NDC on PharmaCompass.

Naprix GMP

Naprix Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Naprix GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Naprix GMP manufacturer or Naprix GMP API supplier for your needs.

Naprix CoA

A Naprix CoA (Certificate of Analysis) is a formal document that attests to Naprix's compliance with Naprix specifications and serves as a tool for batch-level quality control.

Naprix CoA mostly includes findings from lab analyses of a specific batch. For each Naprix CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Naprix may be tested according to a variety of international standards, such as European Pharmacopoeia (Naprix EP), Naprix JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Naprix USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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