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Imidapril

Imidapril

Synopsis, Chemistry

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Also known as: 89396-94-1, Imidapril hcl, Imidapril (hydrochloride), Ta-6366, Imidapril monohydrochloride, Imidapril hydrochloride [jan]

Molecular Formula

C₂₀H₂₈ClN₃O₆

Molecular Weight

441.9 g/mol

InChI Key

LSLQGMMMRMDXHN-GEUPQXMHSA-N

FDA UNII

7NSF9GG1NU

Imidapril Hydrochloride is the hydrochloride salt of imidapril, an angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. As a prodrug, imidapril is converted by hydrolysis in the liver into its active form imidaprilat. Imidaprilat competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Imidaprilat also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.

1 2D Structure

Imidapril

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S)-3-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylic acid;hydrochloride

2.1.2 InChI

InChI=1S/C20H27N3O6.ClH/c1-4-29-19(27)15(11-10-14-8-6-5-7-9-14)21-13(2)17(24)23-16(18(25)26)12-22(3)20(23)28;/h5-9,13,15-16,21H,4,10-12H2,1-3H3,(H,25,26);1H/t13-,15-,16-;/m0./s1

2.1.3 InChI Key

LSLQGMMMRMDXHN-GEUPQXMHSA-N

2.1.4 Canonical SMILES

CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C(CN(C2=O)C)C(=O)O.Cl

2.1.5 Isomeric SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@@H](CN(C2=O)C)C(=O)O.Cl

2.2 Other Identifiers

2.2.1 UNII

7NSF9GG1NU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-methyl-3-(2-(n-(1-ethoxycarbonyl-3-phenylpropyl)amino)propionyl)-2-oxoimidazolidine-4-carboxylic Acid

2. 4-imidazolidinecarboxylic Acid, 3-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1-methyl-2-oxo-, Monohydrochloride, (4s-(3(r*(r*)),4r*))-

3. Imidapril

4. Imidapril Hcl

5. Ta 6366

6. Ta-6366

7. Tanatril

2.3.2 Depositor-Supplied Synonyms

1. 89396-94-1

2. Imidapril Hcl

3. Imidapril (hydrochloride)

4. Ta-6366

5. Imidapril Monohydrochloride

6. Imidapril Hydrochloride [jan]

7. Ta 6366

8. Tanatril

9. 7nsf9gg1nu

10. Novaloc

11. (4s)-3-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylic Acid;hydrochloride

12. 4-imidazolidinecarboxylic Acid, 3-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1-methyl-2-oxo-, Monohydrochloride, (4s-(3(r*(r*)),4r*))-

13. Dsstox_cid_26912

14. Dsstox_rid_82010

15. Dsstox_gsid_46912

16. (4s)-3-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylic Acid,hydrochloride

17. 4-imidazolidinecarboxylic Acid, 3-((2s)-2-(((1s)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1-methyl-2-oxo-, Monohydrochloride, (4s)-

18. Tanapril

19. (s)-3-((s)-2-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1-methyl-2-oxoimidazolidine-4-carboxylic Acid Hydrochloride

20. Cas-89396-94-1

21. Ncgc00181342-01

22. Unii-7nsf9gg1nu

23. Novarok

24. Tanatril (tn)

25. Imidapril Hydrochloride,(s)

26. Palmiticacidpropylester

27. Mls004712066

28. Schembl136722

29. Chembl3183293

30. Dtxsid7046912

31. Imidapril Hydrochloride (jp17)

32. Chebi:31691

33. Hy-b1451

34. Tox21_112801

35. Ac-526

36. Mfcd00923828

37. S2109

38. Akos015994537

39. Tox21_112801_1

40. Bs-1005

41. Ccg-269148

42. Cs-5010

43. Imidapril Hydrochloride [mart.]

44. Sh-6366

45. Imidapril Hydrochloride [who-dd]

46. Imidapril Monohydrochloride [mi]

47. Ncgc00181342-02

48. (4s)-3-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4-imidazolidinecarboxylic Acid Hydrochloride

49. Imidapril Hydrochloride, >=98% (hplc)

50. Smr003475023

51. I0901

52. C77009

53. D01549

54. A917212

55. Q27268625

56. (s)-3-((s)-2-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1-methyl-2-oxoimidazolidine-4-carboxylicacidhydrochloride

57. (s)-3-((s)-2-((s)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)propanoyl)-1-methyl-2-oxoimidazolidine-4-carboxylic Acid Hydrochloride

58. 3-((2s)-2-((1s)-n-(1-ethoxycarbonyl-3-phenylpropyl)amino)-propionyl)-1-methyl-2-oxoimidazolidine-4-carboxylic Acid, Hydrochloride-, 4s-

59. 4-imidazolidinecarboxylic Acid, 3-((2s)-2-(((1s)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1-methyl-2-oxo-, Hydrochloride (1:1), (4s)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₈ClN₃O₆
Molecular Weight	441.9 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	10
Exact Mass	441.1666633 g/mol
Monoisotopic Mass	441.1666633 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	619
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	2

4 Pharmacology and Biochemistry

4.1 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.)