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Azelnidipine

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Also known as: 123524-52-7, 3-(1-benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, Calblock, Azelnidipine [inn], Cs-905, Cs 905

Molecular Formula

C₃₃H₃₄N₄O₆

Molecular Weight

582.6 g/mol

InChI Key

ZKFQEACEUNWPMT-UHFFFAOYSA-N

FDA UNII

PV23P19YUG

Azelnidipine is a dihydropyridine calcium channel blocker. It is marketed by Daiichi-Sankyo pharmaceuticals, Inc. in Japan. It has a gradual onset of action and produces a long-lasting decrease in blood pressure, with only a small increase in heart rate, unlike some other calcium channel blockers. It is currently being studied for post-ischemic stroke management.

1 2D Structure

Azelnidipine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-O-(1-benzhydrylazetidin-3-yl) 5-O-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

2.1.2 InChI

InChI=1S/C33H34N4O6/c1-20(2)42-32(38)27-21(3)35-31(34)29(28(27)24-15-10-16-25(17-24)37(40)41)33(39)43-26-18-36(19-26)30(22-11-6-4-7-12-22)23-13-8-5-9-14-23/h4-17,20,26,28,30,35H,18-19,34H2,1-3H3

2.1.3 InChI Key

ZKFQEACEUNWPMT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C(C(=C(N1)N)C(=O)OC2CN(C2)C(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC(=CC=C5)[N+](=O)[O-])C(=O)OC(C)C

2.2 Other Identifiers

2.2.1 UNII

PV23P19YUG

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(1-diphenylmethylazetidin-3-yl)-5-isopropyl-2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

2. Cs 905

3. Cs-905

2.3.2 Depositor-Supplied Synonyms

1. 123524-52-7

2. 3-(1-benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

3. Calblock

4. Azelnidipine [inn]

5. Cs-905

6. Cs 905

7. Pv23p19yug

8. Ncgc00167436-01

9. Ncgc00167436-02

10. Dsstox_cid_120

11. Dsstox_rid_75382

12. Dsstox_gsid_20120

13. 3,5-pyridinedicarboxylic Acid, 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) Ester

14. 3-o-(1-benzhydrylazetidin-3-yl) 5-o-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

15. Cas-123524-52-7

16. Unii-pv23p19yug

17. Rs-9054

18. Ccris 8650

19. Calblock (tn)

20. Mfcd00865803

21. Azelnidipine [mi]

22. Azelnidipine [jan]

23. Azelnidipine (jp17/inn)

24. Schembl49021

25. Azelnidipine [mart.]

26. 2-amino-1,4-dihydro-6-methyl-4-(3 Nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) Ester

27. 3,5-pyridinedicarboxylic Acid, 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-(1-(diphenylmethyl)-3-azetidinyl) 5-(1-methylethyl) Ester, (+-)-

28. Azelnidipine [who-dd]

29. Chembl1275868

30. Dtxsid3020120

31. Chebi:31247

32. Bcpp000357

33. Hms3651d18

34. Hms3885m05

35. Amy22122

36. Hy-b0023

37. Tox21_112440

38. S3053

39. Akos015841674

40. Tox21_112440_1

41. Ac-2151

42. Bcp9000370

43. Ccg-270140

44. Cs-0949

45. Db09230

46. Ks-1248

47. Pb24693

48. Azelnidipine, >=98% (hplc), Powder

49. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2-amino-6-methyl-4-(3-nitrophenyl)-, 3-(1-(diphenylmethyl)-3-azetidinyl) 5-(1-methylethyl) Ester, (+-)-

50. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2-amino-6-methyl-4-(3-nitrophenyl)-, 3-(1-(diphenylmethyl)-3-azetidinyl)-5-(1-methylethyl) Esster, (+-)-

51. 3-(1-(diphenylmethyl)-3-azetidinyl) 5-isopropyl (+-)-2-amino-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

52. 3-[1-(diphenylmethyl)azetidin-3-yl] 5-(1-methylethyl) 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

53. Ft-0655294

54. Sw219236-1

55. D01145

56. Ab01565841_02

57. 524a527

58. A805113

59. Sr-01000944916

60. Q-200664

61. Q4832365

62. Sr-01000944916-1

63. (+/-)-2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(1-diphenylmethylazetidin-3-yl) Ester 5-isopropyl Ester

64. 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(1-diphenylmethylazetidin-3-yl)ester 5-isopropyl Ester

65. 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-isopropyl Ester

66. 3-(1-(diphenylmethyl)-3-azetidinyl) 5-isopropyl (+/-)-2-amino-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

67. 3-[1-(diphenylmethyl)-3-azetidinyl] 5-isopropyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

68. O3-(1-benzhydrylazetidin-3-yl) O5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;azelnidipine

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₃₄N₄O₆
Molecular Weight	582.6 g/mol
XLogP3	6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	10
Exact Mass	582.24783482 g/mol
Monoisotopic Mass	582.24783482 g/mol
Topological Polar Surface Area	140 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	1080
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of hypertension.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Azelnidipine is a vasodilator that induces a gradual decrease in blood pressure in hypertensive patients. Unlike other members of its drug class, azelnidipine does not induce reflex tachycardia due to vasodilation. This is likely due to the fact that it elicits a gradual fall in blood pressure It also exhibits a prolonged hypotensive effect and has been shown to have a strong anti-arteriosclerotic action in vessels due to its high affinity for vascular tissue and antioxidative activity. Clinical studies have demonstrated that azelnidipine markedly reduced heart rate and proteinuria in hypertensive patients by inhibiting sympathetic nerve activity. Azelnidipine has also been confirmed to have cardio-protective, neuroprotective, and anti-atherosclerotic properties, and has also been found to prevent insulin resistance.

5.2 Absorption, Distribution and Excretion

Absorption

Oral ingestion of azelnidipine demonstrates rapid and dose-dependent absorption.

Route of Elimination

In one study, following a single 4mg oral dose of 14C-labeled azelnidipine in humans, about 26% of the drug was thought to br excreted in the urine and 63% in the feces during the 1 week period post administration.

Volume of Distribution

In a Chinese study examining the pharmacokinetics of the drug, the volume of distribution was found to be 1749 +/- 964.

5.3 Metabolism/Metabolites

Like most members of its class, azelnidipine primarily undergoes first-pass hepatic metabolism. Azelnidipine is metabolized by hepatic cytochrome P450 (CYP) 3A4 and has no active metabolite product. It may interact with other drugs or compounds that are substrates for this enzyme. Azelnidipine is lipophilic and has a potent affinity for membranes of vascular smooth muscle cells.

5.4 Biological Half-Life

16 28 hours.

5.5 Mechanism of Action

Azelnidipine inhibits trans-membrane Ca2+ influx through the voltage-dependent channels of smooth muscles in vascular walls. Ca2+ channels are classified into various categories, including L-type, T-type, N-type, P/Q-type, and R-type Ca2+ channels. The L-type Ca2+ channels. Normally, calcium induces smooth muscle contraction, contributing to hypertension. When calcium channels are blocked, the vascular smooth muscle does not contract, resulting in relaxation of vascular smooth muscle walls and decreased blood pressure.

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