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Nisoldipine

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Chemistry

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Also known as: 63675-72-9, Sular, Nisocor, Baymycard, Nisoldipin, Zadipina

Molecular Formula

C₂₀H₂₄N₂O₆

Molecular Weight

388.4 g/mol

InChI Key

VKQFCGNPDRICFG-UHFFFAOYSA-N

FDA UNII

4I8HAB65SZ

A dihydropyridine calcium channel antagonist that acts as a potent arterial vasodilator and antihypertensive agent. It is also effective in patients with cardiac failure and angina.

Nisoldipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of nisoldipine is as a Calcium Channel Antagonist. The physiologic effect of nisoldipine is by means of Decreased Blood Pressure.

1 2D Structure

Nisoldipine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-O-methyl 5-O-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

2.1.2 InChI

InChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3

2.1.3 InChI Key

VKQFCGNPDRICFG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

4I8HAB65SZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bay K 5552

2.3.2 Depositor-Supplied Synonyms

1. 63675-72-9

2. Sular

3. Nisocor

4. Baymycard

5. Nisoldipin

6. Zadipina

7. Bay K 5552

8. Nisoldipinum

9. Syscor

10. 3-isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

11. Nisoldipinum [inn-latin]

12. Nisoldipino [inn-spanish]

13. Bay-k-5552

14. Bay-k 5552

15. Geomatrix 16e

16. Nisoldipine (stn)

17. Chebi:76917

18. Methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

19. 3-o-methyl 5-o-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

20. Nsc-759106

21. 4i8hab65sz

22. Chembl441428

23. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, Methyl 2-methylpropyl Ester

24. Nisoldipino

25. Nisoldipine 100 Microg/ml In Methanol

26. Ncgc00164633-01

27. Dsstox_cid_3371

28. Dsstox_rid_76999

29. Dsstox_gsid_23371

30. 3-methyl 5-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

31. Smr000466370

32. Cas-63675-72-9

33. Sular (tn)

34. Sr-05000002009

35. Einecs 264-407-7

36. Mfcd00478055

37. Unii-4i8hab65sz

38. Brn 0454188

39. Nisoldipine (jan/usan/inn)

40. Nisoldipine;

41. Nisoldipine,(s)

42. Nisoldipine [usan:inn:ban:jan]

43. (+-)-isobutyl Methyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate

44. Isobutyl 1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)-3-pyridincarboxylat

45. Nisoldipine, ~97%

46. Nisoldipine [mi]

47. Nisoldipine [inn]

48. Nisoldipine [jan]

49. (.+/-.)-nisoldipine

50. Nisoldipine [usan]

51. Nisoldipine [vandf]

52. Baymycard, Norvasc, Syscor

53. Chembl1726

54. Nisoldipine [mart.]

55. Schembl39779

56. (+/-)-nisoldipine

57. Nisoldipine [usp-rs]

58. Nisoldipine [who-dd]

59. 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl 2-methylpropyl Ester

60. Mls000759498

61. Mls001424102

62. Mls002153943

63. Bidd:gt0684

64. Gtpl2524

65. Chembl3192341

66. Dtxsid0023371

67. Nisoldipine, >=98% (hplc)

68. Nisoldipine [orange Book]

69. Hms2051o18

70. Hms2089k20

71. Hms2093f15

72. Hms2097e13

73. Hms2231l20

74. Hms3393o18

75. Hms3651k17

76. Hms3714e13

77. Hms3744o19

78. Hms3884i08

79. Pharmakon1600-01505390

80. Bcp22696

81. Tox21_112251

82. Tox21_302365

83. Ac-987

84. Bbl028683

85. Bdbm50101963

86. Bdbm50227259

87. Dl-255

88. Nsc759106

89. S1748

90. Stk631543

91. Akos005563632

92. Akos037515714

93. Tox21_112251_1

94. Ccg-100894

95. Ccg-213412

96. Cs-1131

97. Db00401

98. Ks-5188

99. Nc00144

100. Nsc 759106

101. Bay K 5552;bay-k 5552;sular

102. Isobutyl Methyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate

103. O5-isobutyl O3-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

104. Ncgc00164633-02

105. Ncgc00164633-03

106. Ncgc00255136-01

107. 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic Acid Isobutyl Methyl Ester

108. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, Methyl 2-methylpropyl Ester, (+-)-

109. 6-bromo-2,3-dimethoxybenzoicacid

110. Bn164147

111. Hy-17402

112. (+/-)-bay-k-5552

113. Sbi-0206830.p001

114. ((c)i)-nisoldipine-d4(2-nitrophenyl-d4)

115. Ft-0601599

116. N0900

117. Sw219237-1

118. C07699

119. D00618

120. Ab01275444-01

121. Ab01275444_02

122. 675n729

123. A834466

124. Q3342150

125. Sr-05000002009-1

126. Sr-05000002009-2

127. Sr-05000002009-3

128. Brd-a84465106-001-01-2

129. Z277942268

130. 3-isobutyl5-methyl2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

131. Isobutyl Methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

132. (.+/-.)-isobutyl Methyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate

133. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, 3-methyl 5-(2-methylpropyl) Ester

134. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, Methyl 2-methylpropyl Ester, (+/-)-

135. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, Methyl 2-methylpropyl Ester, (.+/-.)-

136. 3-isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate #

137. Methyl 2-methylpropyl-1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate, Dl-

138. O5-isobutyl O3-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;nisoldipine

139. O5-methyl O3-(2-methylpropyl) 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₄N₂O₆
Molecular Weight	388.4 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Exact Mass	388.16343649 g/mol
Monoisotopic Mass	388.16343649 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	704
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 Information

1 of 4
Drug Name	Nisoldipine
PubMed Health	Nisoldipine (By mouth)
Drug Classes	Antianginal, Antihypertensive, Cardiovascular Agent
Drug Label	Nisoldipine is an extended-release tablet dosage form of the dihydropyridine calcium channel blocker nisoldipine. Nisoldipine is ()-Isobutyl methyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate, C20H24N2O6, and has the struct...
Active Ingredient	Nisoldipine
Dosage Form	Tablet, extended release
Route	Oral
Strength	34mg; 8.5mg; 30mg; 25.5mg; 17mg; 40mg; 20mg
Market Status	Prescription
Company	Mylan

2 of 4
Drug Name	Sular
PubMed Health	Nisoldipine (By mouth)
Drug Classes	Antianginal, Antihypertensive, Cardiovascular Agent
Drug Label	SULAR (nisoldipine) is an extended release tablet dosage form of the dihydropyridine calcium channel blocker nisoldipine. Nisoldipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, methyl 2-methylpropyl ester, C20H24...
Active Ingredient	Nisoldipine
Dosage Form	Tablet, extended release
Route	Oral
Strength	34mg; 8.5mg; 17mg
Market Status	Prescription
Company	Shionogi

3 of 4
Drug Name	Nisoldipine
PubMed Health	Nisoldipine (By mouth)
Drug Classes	Antianginal, Antihypertensive, Cardiovascular Agent
Drug Label	Nisoldipine is an extended-release tablet dosage form of the dihydropyridine calcium channel blocker nisoldipine. Nisoldipine is ()-Isobutyl methyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate, C20H24N2O6, and has the struct...
Active Ingredient	Nisoldipine
Dosage Form	Tablet, extended release
Route	Oral
Strength	34mg; 8.5mg; 30mg; 25.5mg; 17mg; 40mg; 20mg
Market Status	Prescription
Company	Mylan

4 of 4
Drug Name	Sular
PubMed Health	Nisoldipine (By mouth)
Drug Classes	Antianginal, Antihypertensive, Cardiovascular Agent
Drug Label	SULAR (nisoldipine) is an extended release tablet dosage form of the dihydropyridine calcium channel blocker nisoldipine. Nisoldipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, methyl 2-methylpropyl ester, C20H24...
Active Ingredient	Nisoldipine
Dosage Form	Tablet, extended release
Route	Oral
Strength	34mg; 8.5mg; 17mg
Market Status	Prescription
Company	Shionogi

4.2 Drug Indication

For the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nisoldipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Nisoldipine is similar to other peripheral vasodilators. Nisoldipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial 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.

5.2 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.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

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 FDA Pharmacological Classification

5.3.1 Active Moiety

NISOLDIPINE

5.3.2 FDA UNII

4I8HAB65SZ

5.3.3 Pharmacological Classes

Decreased Blood Pressure [PE]; Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]

5.4 ATC Code

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA07 - Nisoldipine

5.5 Absorption, Distribution and Excretion

Absorption

Relatively well absorbed into the systemic circulation with 87% of the radiolabeled drug recovered in urine and feces. The absolute bioavailability of nisoldipine is about 5%.

Route of Elimination

Although 60-80% of an oral dose undergoes urinary excretion, only traces of unchanged nisoldipine are found in urine.

5.6 Metabolism/Metabolites

Pre-systemic metabolism in the gut wall, and this metabolism decreases from the proximal to the distal parts of the intestine. Nisoldipine is highly metabolized; 5 major urinary metabolites have been identified. The major biotransformation pathway appears to be the hydroxylation of the isobutyl ester. A hydroxylated derivative of the side chain, present in plasma at concentrations approximately equal to the parent compound, appears to be the only active metabolite and has about 10% of the activity of the parent compound. Cytochrome P450 enzymes are believed to play a major role in the metabolism of nisoldipine. The particular isoenzyme system responsible for its metabolism has not been identified, but other dihydropyridines are metabolized by cytochrome P450 IIIA4.

Nisoldipine has known human metabolites that include 2,6-Dimethyl-5-(2-methylpropoxycarbonyl)-4-(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid, 5-O-(1-hydroxy-2-methylpropyl) 3-O-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and Dehydro Nisoldipine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.7 Biological Half-Life

7-12 hours

5.8 Mechanism of Action

By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, Nisoldipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes The decrease in intracellular calcium inhibits the contractile processes of the myocardial 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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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 10MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 10MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**