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Cilnidipine

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Chemistry

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Also known as: 132203-70-4, Cinalong, Atelec, Siscard, Frc-8653, Frc 8653

Molecular Formula

C₂₇H₂₈N₂O₇

Molecular Weight

492.5 g/mol

InChI Key

KJEBULYHNRNJTE-DHZHZOJOSA-N

FDA UNII

4LNU2SU262

Cilnidipine is a dihydropyridine calcium antagonist. It was jointly developed by Fuji Viscera Pharmaceutical Company, Japan and Ajinomoto, Japan and approved in 1995. Compared with other calcium antagonists, cilnidipine can act on the N-type calcium channel that existing sympathetic nerve end besides acting on L-type calcium channel that similar to most of the calcium antagonists. This drug is approved in China, Japan, Korea, India, and several countries in the European Union.

1 2D Structure

Cilnidipine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-O-(2-methoxyethyl) 5-O-[(E)-3-phenylprop-2-enyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

2.1.2 InChI

InChI=1S/C27H28N2O7/c1-18-23(26(30)35-14-8-11-20-9-5-4-6-10-20)25(21-12-7-13-22(17-21)29(32)33)24(19(2)28-18)27(31)36-16-15-34-3/h4-13,17,25,28H,14-16H2,1-3H3/b11-8+

2.1.3 InChI Key

KJEBULYHNRNJTE-DHZHZOJOSA-N

2.1.4 Canonical SMILES

CC1=C(C(C(=C(N1)C)C(=O)OCC=CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OCCOC

2.1.5 Isomeric SMILES

CC1=C(C(C(=C(N1)C)C(=O)OC/C=C/C2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OCCOC

2.2 Other Identifiers

2.2.1 UNII

4LNU2SU262

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-methoxyethyl-3-phenyl-2-propen-1-yl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

2. Cilnidipine, (+)-isomer

3. Cilnidipine, (-)-isomer

4. Frc 8653

5. Frc-8653

2.3.2 Depositor-Supplied Synonyms

1. 132203-70-4

2. Cinalong

3. Atelec

4. Siscard

5. Frc-8653

6. Frc 8653

7. 3-cinnamyl 5-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

8. Cilnidipine [inn]

9. Chebi:31399

10. Cilnidipine, (+)-

11. Cilnidipine, (-)-

12. (+-)-(e)-cinnamyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

13. 97t5az1jip

14. 4lnu2su262

15. S85436zg85

16. 2-methoxyethyl (2e)-3-phenylprop-2-en-1-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

17. Ncgc00162150-01

18. Cinaldipine

19. (+)-frc-8653

20. (-)-frc-8653

21. Dsstox_cid_26309

22. Dsstox_rid_81530

23. Dsstox_gsid_46309

24. (e)-cinnamyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

25. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-methoxyethyl 3-phenyl-2-propenyl Ester, (e)-(+)-

26. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-methoxyethyl 3-phenyl-2-propenyl Ester, (e)-(-)-

27. Atelec (tn)

28. Cas-132203-70-4

29. Sr-05000001454

30. 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 2-methoxyethyl (2e)-3-phenyl-2-propenyl Ester

31. Unii-97t5az1jip

32. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl) 5-((2e)-3-phenyl-2-propen-1-yl) Ester

33. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl) 5-[(2e)-3-phenyl-2-propen-1-yl] Ester

34. Cilnidipine- Bio-x

35. Mfcd00865853

36. Cilnidipine [mi]

37. Cilnidipine [jan]

38. Cilnidipine (jp17/inn)

39. Cilnidipine [mart.]

40. Unii-4lnu2su262

41. Schembl25550

42. Cilnidipine [who-dd]

43. 3-o-(2-methoxyethyl) 5-o-[(e)-3-phenylprop-2-enyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

44. Chembl452076

45. Gtpl7767

46. Dtxsid0046309

47. Unii-s85436zg85

48. Chebi:91506

49. Hms2089j07

50. Hms3261e06

51. Hms3413l13

52. Hms3677l13

53. Hms3715n17

54. Hms3884k09

55. Bcp22689

56. Tox21_112001

57. Tox21_500422

58. Ac-270

59. Bdbm50101813

60. S1293

61. Stk623341

62. Akos005558085

63. Tox21_112001_1

64. Ccg-221188

65. Ccg-221726

66. Cilnidipine, >=98% (hplc), Powder

67. Cs-1133

68. Db09232

69. Ks-1294

70. Lp00422

71. Sdccgsbi-0633712.p001

72. Ncgc00162150-02

73. Ncgc00162150-03

74. Ncgc00162150-04

75. Ncgc00162150-16

76. Ncgc00261107-01

77. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-methoxyethyl 3-phenyl-2-propenyl Ester, (e)-(+-)-

78. Bc164309

79. Hy-17404

80. Ls-15175

81. Sw219784-1

82. D01173

83. T70209

84. Ab01274755-01

85. Ab01274755-02

86. Ab01274755_03

87. Frc-8653; Frc 8653; Frc8653

88. 203c704

89. Q731525

90. J-006141

91. Sr-05000001454-1

92. Sr-05000001454-2

93. Brd-a07875874-001-01-6

94. F2173-0669

95. (+/-)-(e)-cinnamyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

96. 102106-21-8

97. 118934-76-2

98. 118934-77-3

99. 132295-21-7

100. 132338-87-5

101. 2-methoxyethyl (2e)-3-phenyl-2-propenyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

102. O3-(2-methoxyethyl) O5-(3-phenylprop-2-enyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₈N₂O₇
Molecular Weight	492.5 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	11
Exact Mass	492.18965124 g/mol
Monoisotopic Mass	492.18965124 g/mol
Topological Polar Surface Area	120 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	896
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Cilnidipine is indicated for the management of hypertension for end-organ protection. It is reported to be useful in elderly patients and in those with diabetes and albuminuria. Cilnidipine has been increasingly used in patients with chronic kidney disease Hypertension is the term used to describe the presence of high blood pressure. The blood pressure is generated by the force of the blood pumped from the heart against the blood vessels. Thus hypertension is caused when there is too much pressure on the blood vessels and this effect can damage the blood vessel.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Administration of cilnidipine has been shown to present an antisympathetic profile in vitro and in vivo. It decreases blood pressure safely and effectively without excessive blood pressure reduction or tachycardia.

5.2 MeSH Pharmacological Classification

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

5.3 ATC Code

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA14 - Cilnidipine

5.4 Absorption, Distribution and Excretion

Absorption

Cilnidipine presents a very rapid absorption with a maximum peaked concentration after 2 hours. Its distribution tends to be higher in the liver as well as in kidneys, plasma and other tissues. Cilnidipine does not present a high accumulation in the tissue after repeated oral administration. Cilnidipine is reported to present very low bioavailability determined to be approximately 13%. This low bioavailability is suggested to be due to its low aqueous solubility and high permeability. Hence, efforts have been made in order to find an innovative formulation that can significantly improve the bioavailability of this drug. One of these formulations corresponds to the generation of polymeric nanoparticles which enhance the bioavailability by 2.5-3-fold.

Route of Elimination

Cilnidipine gets eliminated through the urine in a proportion of 20% of the administered dose and 80% is eliminated by the feces.

Volume of Distribution

Drugs on the group of dihydropyridines such as cilnidipine tend to have a large volume of distribution.

5.5 Metabolism/Metabolites

Cilnidipine is metabolized by both liver and kidney. It is rapidly metabolized by liver microsomes by a dehydrogenation process. The major enzymatic isoform involved in cilnidipine dehydrogenation of the dihydropyridine ring is CYP3A.

5.6 Biological Half-Life

The half-life of the hypotensive effect for cilnidipine is of about 20.4 min.

5.7 Mechanism of Action

Cilnidipine acts on the L-type calcium channels of blood vessels by blocking the incoming calcium and suppressing the contraction of blood vessels, thereby reducing blood pressure. Cilnidipine also works on the N-type calcium channel located at the end of the sympathetic nerve, inhibiting the emission of norepinephrine and suppressing the increase in stress blood pressure.

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