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Enalaprilat

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Synopsis

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Chemistry

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Also known as: 76420-72-9, Enalapril acid, Enalaprilate, Enalaprilatum, Enalaprilic acid, Enalaprilat anhydrous

Molecular Formula

C₁₈H₂₄N₂O₅

Molecular Weight

348.4 g/mol

InChI Key

LZFZMUMEGBBDTC-QEJZJMRPSA-N

FDA UNII

Q508Q118JM

The active metabolite of ENALAPRIL and one of the potent, intravenously administered, ANGIOTENSIN-CONVERTING ENZYME INHIBITORS. It is an effective agent for the treatment of essential hypertension and has beneficial hemodynamic effects in heart failure. The drug produces renal vasodilation with an increase in sodium excretion.

Enalaprilat anhydrous is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of enalaprilat anhydrous is as an Angiotensin-converting Enzyme Inhibitor. The physiologic effect of enalaprilat anhydrous is by means of Decreased Blood Pressure.

1 2D Structure

Enalaprilat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]propanoyl]pyrrolidine-2-carboxylic acid

2.1.2 InChI

InChI=1S/C18H24N2O5/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25)/t12-,14-,15-/m0/s1

2.1.3 InChI Key

LZFZMUMEGBBDTC-QEJZJMRPSA-N

2.1.4 Canonical SMILES

CC(C(=O)N1CCCC1C(=O)O)NC(CCC2=CC=CC=C2)C(=O)O

2.1.5 Isomeric SMILES

C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N[C@@H](CCC2=CC=CC=C2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

Q508Q118JM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(n-((s)-1-carboxy-3-phenylpropyl)-l-alanyl)-l-proline Dihydrate

2. Enalaprilat Anhydrous

3. Enalaprilat Citrate, Anhydrous

4. Enalaprilat Dihydrate

5. Enalaprilat, (r)-isomer, Anhydrous

6. Enalaprilic Acid

7. Mk 422

8. Mk-422

9. Mk422

10. Pres Iv

11. Vasotec

12. Xanef

2.3.2 Depositor-Supplied Synonyms

1. 76420-72-9

2. Enalapril Acid

3. Enalaprilate

4. Enalaprilatum

5. Enalaprilic Acid

6. Enalaprilat Anhydrous

7. Enalapril Diacid

8. Enalaprilat (anhydrous)

9. (s)-1-((s)-2-(((s)-1-carboxy-3-phenylpropyl)amino)propanoyl)pyrrolidine-2-carboxylic Acid

10. N-[(1s)-1-carboxy-3-phenylpropyl]-l-alanyl-l-proline

11. Mk-422

12. Enalaprilat [inn]

13. Chebi:4786

14. Q508q118jm

15. 1-((2s)-2-{[(1s)-1-carboxy-3-phenylpropyl]amino}propanoyl)-l-proline

16. ((s)-1-carboxy-3-phenylpropyl)-l-alanyl-l-proline

17. Eal

18. L-proline, N-((1s)-1-carboxy-3-phenylpropyl)-l-alanyl-

19. L-proline, N-[(1s)-1-carboxy-3-phenylpropyl]-l-alanyl-

20. Enalaprilat Inhibitor

21. (2s)-1-[(2s)-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]propanoyl]pyrrolidine-2-carboxylic Acid

22. Smr000466359

23. Enalaprilat [spanish]

24. Mk 421 Diacid

25. Chembl577

26. Enalaprilate [french]

27. Enalaprilatum [latin]

28. Mk 422

29. Unii-q508q118jm

30. Enalaprilat,(s)

31. (s)-1-((s)-2-((s)-1-carboxy-3-phenylpropylamino)propanoyl)pyrrolidine-2-carboxylic Acid

32. (2s)-1-((2s)-2-(((1s)-1-carboxy-3-phenylpropyl)amino)propanoyl)pyrrolidine-2-carboxylic Acid

33. (2s)-1-[(2s)-2-{[(1s)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic Acid

34. Einecs 278-459-3

35. Mfcd00865786

36. Schembl37289

37. (2s)-1-[(2s)-2-[[(2s)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic Acid

38. Mls000759476

39. Mls001424138

40. Bidd:gt0752

41. Gtpl6332

42. N-(1(s)-carboxy-3-phenylpropyl)-l-alanyl-l-proline

43. Enalaprilat, Analytical Standard

44. Dtxsid0048975

45. Hy-b0231a

46. Hms2051h16

47. Hms2089p04

48. Hms2232b19

49. Hms3263o13

50. Pharmakon1600-01503833

51. Zinc3812851

52. Tox21_501036

53. Bdbm50367254

54. Nsc760053

55. Akos015840130

56. Akos015892570

57. Ccg-101042

58. Db09477

59. Lp01036

60. Nc00292

61. Sdccgsbi-0633781.p001

62. Ncgc00164593-01

63. Ncgc00164593-11

64. Ncgc00261721-01

65. As-13013

66. Cs-0012359

67. E1302

68. Ab00698268-05

69. Ab00698268-07

70. Ab00698268-08

71. Ab00698268_09

72. Ab00698268_10

73. Enalapril Diacid Dihydrate Anhydrous [mi]

74. 420e729

75. Enalapril Maleate Impurity C [ep Impurity]

76. Sr-01000763426

77. Q5375179

78. Sr-01000763426-3

79. W-104365

80. N-[(s)-1-carboxy-3-phenyl-propyl]-l-alanyl-l-proline

81. 1-(n-((s)-1-carboxy-3-phenylpropyl)-l-alanyl)-l-proline

82. L-proline, 1-(n-(1-carboxt-3-phenylpropyl)-l-alanyl)-, (s)-

83. L-proline, 1-(n-(1-carboxy-3-phenylpropyl)-l-alanyl)-, (s)-

84. (s)-1-((s)-2-(((s)-1-carboxy-3-phenylpropyl)amino)propanoyl)pyrrolidine-2-carboxylicacid

85. (2s)-1-[(2s)-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]propanoyl]pyrrolidine-2-carboxylic Acid (enalaprilat)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₄N₂O₅
Molecular Weight	348.4 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Exact Mass	348.16852187 g/mol
Monoisotopic Mass	348.16852187 g/mol
Topological Polar Surface Area	107 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	490
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Enalaprilat
PubMed Health	Enalaprilat (Injection)
Drug Classes	Antihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug Label	Enalaprilat injection USP is a sterile aqueous solution for intravenous administration. Enalaprilat is an angiotensin-converting enzyme inhibitor. It is chemically described as (S)-1-[N-(1-carboxy-3-phenylpropyl)-L-alanyl]-L-proline dihydrate. Its st...
Active Ingredient	Enalaprilat
Dosage Form	Injectable
Route	Injection
Strength	1.25mg/ml
Market Status	Prescription
Company	Bedford; Hospira; Hikma Farmaceutica; Teva Pharms Usa

2 of 2
Drug Name	Enalaprilat
PubMed Health	Enalaprilat (Injection)
Drug Classes	Antihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug Label	Enalaprilat injection USP is a sterile aqueous solution for intravenous administration. Enalaprilat is an angiotensin-converting enzyme inhibitor. It is chemically described as (S)-1-[N-(1-carboxy-3-phenylpropyl)-L-alanyl]-L-proline dihydrate. Its st...
Active Ingredient	Enalaprilat
Dosage Form	Injectable
Route	Injection
Strength	1.25mg/ml
Market Status	Prescription
Company	Bedford; Hospira; Hikma Farmaceutica; Teva Pharms Usa

4.2 Drug Indication

Enalaprilat injection is indicated for the treatment of hypertension when oral therapy is not practical.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Enalaprilat injection results in the reduction of both supine and standing systolic and diastolic blood pressure, usually with no orthostatic component. Symptomatic postural hypotension is therefore infrequent, although it might be anticipated in volume-depleted patients. The onset of action usually occurs within fifteen minutes of administration with the maximum effect occurring within one to four hours. The abrupt withdrawal of enalaprilat has not been associated with a rapid increase in blood pressure. The duration of hemodynamic effects appears to be dose-related. However, for the recommended dose, the duration of action in most patients is approximately six hours. Following administration of enalapril, there is an increase in renal blood flow; glomerular filtration rate is usually unchanged. The effects appear to be similar in patients with renovascular hypertension.

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

ENALAPRILAT ANHYDROUS

5.3.2 FDA UNII

Q508Q118JM

5.3.3 Pharmacological Classes

Angiotensin-converting Enzyme Inhibitors [MoA]; Decreased Blood Pressure [PE]; Angiotensin Converting Enzyme Inhibitor [EPC]

5.4 Absorption, Distribution and Excretion

Absorption

Enalaprilat is poorly absorbed following oral administration, and is therefore only available as an intravenous injection.

Route of Elimination

Excretion of enalaprilat is primarily renal with more than 90 percent of an administered dose recovered in the urine as unchanged drug within 24 hours.

Clearance

The disposition of enalaprilat in patients with renal insufficiency is similar to that in patients with normal renal function until the glomerular filtration rate is 30 mL/min or less. Renal clearance was 158 47 ml/min.

5.5 Metabolism/Metabolites

Both enalapril and enalaprilat undergo renal excretion without further metabolism.

5.6 Biological Half-Life

11 hr

5.7 Mechanism of Action

Enalaprilat is the active metabolite of the orally available pro-drug, enalapril. Used in the treatment of hypertension, enalapril is an ACE inhibitor that prevents Angiotensin Converting Enzyme (ACE) from transforming angiotensin I into angiotensin II. As angiotensin II is responsible for vasoconstriction and sodium reabsorption in the proximal tubule of the kidney, down-regulation of this protein results in reduced blood pressure and blood fluid volume

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