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Also known as: 82834-16-0, S-9490, Perindoprilum, Mcn-a-2833, Coversyl, Chebi:8024
Molecular Formula
C19H32N2O5
Molecular Weight
368.5  g/mol
InChI Key
IPVQLZZIHOAWMC-QXKUPLGCSA-N
FDA UNII
Y5GMK36KGY

CAS 82834-16-0
An angiotensin-converting enzyme inhibitor. It is used in patients with hypertension and heart failure.
Perindopril is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of perindopril is as an Angiotensin-converting Enzyme Inhibitor.
1 2D Structure

CAS 82834-16-0

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,3aS,7aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid
2.1.2 InChI
InChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,15-,16-/m0/s1
2.1.3 InChI Key
IPVQLZZIHOAWMC-QXKUPLGCSA-N
2.1.4 Canonical SMILES
CCCC(C(=O)OCC)NC(C)C(=O)N1C2CCCCC2CC1C(=O)O
2.1.5 Isomeric SMILES
CCC[C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)O
2.2 Other Identifiers
2.2.1 UNII
Y5GMK36KGY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Erbumine, Perindopril

2. Perindopril Erbumine

3. Perstarium

4. Pirindopril

5. S 9490

6. S 9490 3

7. S 9490-3

8. S 94903

9. S-9490

10. S9490

2.3.2 Depositor-Supplied Synonyms

1. 82834-16-0

2. S-9490

3. Perindoprilum

4. Mcn-a-2833

5. Coversyl

6. Chebi:8024

7. (2s,3as,7as)-1-[(2s)-2-[[(2s)-1-ethoxy-1-oxopentan-2-yl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic Acid

8. Y5gmk36kgy

9. (2s,3as,7as)-1-[(2s)-2-{[(2s)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1h-indole-2-carboxylic Acid

10. Dsstox_cid_3440

11. Dsstox_rid_77030

12. Dsstox_gsid_23440

13. (2s,3as,7as)-1-((s)-n-((s)-1-carboxybutyl)alanyl)hexahydro-2-indolinecarboxylic Acid, 1-ethyl Ester

14. Prestarium

15. Coverex

16. Coversum

17. Coverene Cor

18. Cas-82834-16-0

19. Perindoprilum [latin]

20. Unii-y5gmk36kgy

21. Perindopril (usan/inn)

22. Perindopril [usan:inn:ban]

23. Mcn-a 2833

24. S 9490

25. Ncgc00159509-02

26. Sed-9490

27. Dw-7950

28. Brn 4300272

29. Spectrum_001948

30. Perindopril [mi]

31. Spectrum2_001108

32. Spectrum3_001683

33. Spectrum4_000775

34. Spectrum5_001689

35. Perindopril [inn]

36. Perindopril [usan]

37. Perindopril [vandf]

38. Chembl1581

39. Perindopril [mart.]

40. Schembl16205

41. Bspbio_003206

42. Kbiogr_001190

43. Kbioss_002502

44. Perindopril [who-dd]

45. Mls002154153

46. Bidd:gt0786

47. Spbio_001216

48. Gtpl6367

49. Dtxsid6023440

50. Kbio2_002494

51. Kbio2_005062

52. Kbio2_007630

53. Kbio3_002426

54. Hms2098m04

55. Hms2232m24

56. Hms3715m04

57. Ex-a6377

58. Hy-b0130

59. Zinc3812867

60. Tox21_113087

61. Bdbm50493988

62. Akos025311315

63. Tox21_113087_1

64. Ccg-221101

65. Cs-1903

66. Db00790

67. Ncgc00274070-01

68. (2s)-2-[(1s)-1-carbethoxybutylamino]-1-oxopropyl-(2s,3as,7as)-perhydroindole-2-carboxylic Acid

69. (2s,3as,7as)-1-[(2s)-2-{[(2s)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1h-indole-2-carboxylic Acid

70. Ethyl N-{(2s)-1-[(2s,3as,7as)-2-carboxyoctahydro-1h-indol-1-yl]-1-oxopropan-2-yl}-l-norvalinate

71. Smr001233453

72. Sbi-0206736.p001

73. C07706

74. D03753

75. Ab00918721_06

76. 834p160

77. Q277785

78. S-90652

79. Sr-01000841817

80. J-523913

81. Sr-01000841817-2

82. Brd-k92731339-227-02-3

83. Brd-k92731339-227-03-1

84. (2s,3as,7as)-1-((s)-n-((s)-1-carboxybutyl)alanyl)hexahydro-2-indolinecarboxylicacid1-ethylester

85. (2s,3as,7as)-1-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-2-pent-yl]amino]propanoyl]-octahydro-1h-indole-2-carboxylic Acid

86. (2s,3as,7as)-1-{(2s)-2-[(1s)-1-(ethoxycarbonyl)butylamino]propionyl}octahydro-1h-indole-2-carboxylic Acid

87. 11h-indole-2-carboxylic Acid, Octahydro-1-(2-((1-ethoxycarbonyl)butyl)amino)-1-oxopropyl)-, (2s-(1(r*(r*)),2-alpha,3a-beta,7a-beta))-

88. 1h-indole-2-carboxylic Acid, 1-(2-((1-(ethoxycarbonyl)butyl)amino)-1-oxopropyl)octahydro-, (2s-(1(r*(r*)),2.alpha.,3a.beta.,7a.beta.))-

89. 1h-indole-2-carboxylic Acid, 1-(2-((1-(ethoxycarbonyl)butyl)amino)-1-oxopropyl)octahydro-, (2s-(1(r*(r*)),2alpha,3abeta,7abeta))-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 368.5 g/mol
Molecular Formula C19H32N2O5
XLogP30.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass368.23112213 g/mol
Monoisotopic Mass368.23112213 g/mol
Topological Polar Surface Area95.9 Ų
Heavy Atom Count26
Formal Charge0
Complexity524
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 Indication

For the treatment of mild to moderate essential hypertension, mild to moderate congestive heart failure, and to reduce the cardiovascular risk of individuals with hypertension or post-myocardial infarction and stable coronary disease.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Perindopril is a nonsulfhydryl prodrug that is metabolized via first pass effect (62%) and systemic hydrolysis (38%) to perindoprilat, its active metabolite, following oral administration. Perindoprilat lowers blood pressure 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 perindoprilat by causing increased vasodilation and decreased blood pressure.


5.2 MeSH Pharmacological Classification

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.)


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PERINDOPRIL
5.3.2 FDA UNII
Y5GMK36KGY
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - Angiotensin-converting Enzyme Inhibitors
5.4 ATC Code

C09AA04

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

C09AA04 - Perindopril


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed with peak plasma concentrations occurring approximately 1 hour after oral administration. Bioavailability is 65-75%. Following absorption, perindopril is hydrolyzed to perindoprilat, which has an average bioavailability of 20%. The rate and extent of absorption is unaffected by food. However, food decreases the extent of biotransformation to peridoprilat and reduces its bioavailability by 35%.


Route of Elimination

Perindopril is extensively metabolized following oral administration, with only 4 to 12% of the dose recovered unchanged in the urine.


Clearance

219 - 362 mL/min [oral administration]


5.6 Metabolism/Metabolites

Extensively metabolized, with only 4-12% of the dose recovered in urine following oral administration. Six metabolites have been identified: perindoprilat, perindopril glucuronide, perindoprilat glucuronide, a perindopril lactam, and two perindoprilat lactams. Only perindoprilat is pharmacologically active. Peridoprilat and perindoprilat glucuronide are the two main circulating metabolites.


Perindopril has known human metabolites that include Perindoprilat glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

Perindopril, 1.2 hours; Peridoprilat, 30-120 hours. The long half life of peridoprilat is due to its slow dissociation from ACE binding sites.


5.8 Mechanism of Action

There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Perindoprilat, the active metabolite of perindopril, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Perindopril also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors.


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