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Nilvadipine

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Synopsis

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Chemistry

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Also known as: 75530-68-6, Escor, Nivadil, Nivadipine, Fr-34235, Fk 235

Molecular Formula

C₁₉H₁₉N₃O₆

Molecular Weight

385.4 g/mol

InChI Key

FAIIFDPAEUKBEP-UHFFFAOYSA-N

FDA UNII

0214FUT37J

Nilvadipine is a calcium channel blocker (CCB) for the treatment of hypertension.

1 2D Structure

Nilvadipine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C19H19N3O6/c1-10(2)28-19(24)15-11(3)21-14(9-20)17(18(23)27-4)16(15)12-6-5-7-13(8-12)22(25)26/h5-8,10,16,21H,1-4H3

2.1.3 InChI Key

FAIIFDPAEUKBEP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C(C(=C(N1)C#N)C(=O)OC)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OC(C)C

2.2 Other Identifiers

2.2.1 UNII

0214FUT37J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-isopropyl-3-methyl-2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinecarboxylate

2. Escor

3. Fr 34235

4. Fr-34235

5. Nivadil

2.3.2 Depositor-Supplied Synonyms

1. 75530-68-6

2. Escor

3. Nivadil

4. Nivadipine

5. Fr-34235

6. Fk 235

7. Nivadip

8. Dl-nilvadipine

9. Fr 34235

10. Sk&f 102,362

11. Cl 287,389

12. Fk-235

13. Cl-287389

14. Nilvadipine (arc029)

15. Sk&f-102362

16. 5-isopropyl 3-methyl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

17. 3-o-methyl 5-o-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

18. Cl-287,389

19. 0214fut37j

20. 5-isopropyl 3-methyl 2-cyano-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

21. Skf-102362

22. 3,5-pyridinedicarboxylic Acid, 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-methyl 5-(1-methylethyl) Ester

23. Fr34235

24. Ncgc00167435-01

25. Sk&f-102,362

26. Nilvadipinum [latin]

27. Nilvadipino [spanish]

28. Nivaldipine

29. Nilvadipino

30. Nilvadipinum

31. 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-methyl 5-(1-methylethyl) Ester

32. Nilvadipine [usan:inn:jan]

33. Arc029

34. Brn 3572609

35. Unii-0214fut37j

36. Nivadil (tn)

37. Mfcd00867065

38. Nilvadipine [mi]

39. Nilvadipine [inn]

40. Nilvadipine [jan]

41. Nilvadipine [usan]

42. Dsstox_cid_26624

43. Dsstox_rid_81774

44. Nilvadipine [mart.]

45. Dsstox_gsid_46624

46. Schembl33729

47. (+/-)-nilvadipine

48. Nilvadipine [who-dd]

49. Chembl517427

50. Dtxsid2046624

51. Chebi:31911

52. Faiifdpaeukbep-uhfffaoysa-

53. Gtpl10160

54. Nilvadipine (jp17/usan/inn)

55. Fk235

56. Hms3651j11

57. Hms3714a17

58. Hms3884f16

59. Bcp06007

60. Arc029;fr34235

61. Tox21_112439

62. Bdbm50103634

63. Akos015907577

64. Ccg-220648

65. Db06712

66. Ks-1303

67. Ncgc00167435-02

68. Ncgc00167435-03

69. Ncgc00167435-07

70. 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 5-isopropyl 3-methyl Ester

71. 3,5-pyridinedicarboxylic Acid, 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-methyl-5-(1-methylethyl) Ester

72. 3-methyl 5-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

73. 5-isopropyl 3-methyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

74. Ac-28326

75. Hy-14284

76. O3-methyl O5-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

77. Cas-75530-68-6

78. Db-055963

79. Ft-0630839

80. N0899

81. S2721

82. Sw219572-1

83. D01908

84. Ab01566895_01

85. 530n686

86. A838445

87. Sr-01000872715

88. Q7037489

89. Sr-01000872715-1

90. O3-methyl O5-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-

91. (+)-5-isopropyl 3-methyl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

92. 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic Acid O3-methyl Ester O5-propan-2-yl Ester

93. 5-isopropyl 3-methyl (+)-2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

94. 5-isopropyl 3-methyl (-)-2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

95. 5-isopropyl3-methyl 2-cyano-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₉N₃O₆
Molecular Weight	385.4 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	6
Exact Mass	385.12738533 g/mol
Monoisotopic Mass	385.12738533 g/mol
Topological Polar Surface Area	134 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	783
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 management of vasospastic angina, chronic stable angina and hypertension.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nilvadipine is similar to other dihydropyridines including amlodipine, felodipine, isradipine, and nicardipine. Nilvadipine is used to treat Prinzmetal's angina, hypertension, and other vascular disorders such as Raynaud's phenomenon. By blocking the calcium channels, Nifedipine inhibits the spasm of the coronary artery and dilates the systemic arteries, results in a increase of myocardial oxygen supply and a decrease in systemic blood pressure.

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.)

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 ATC Code

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA10 - Nilvadipine

5.4 Mechanism of Action

Nilvadipine inhibits the influx of extracellular calcium through myocardial and vascular membrane pores by physically plugging the channel. The decrease in intracellular calcium inhibits the contractile processes of smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

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