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Nicardipine

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

INJECTABLE;INTRAVENOUS - 20MG/200ML (0.1MG/ML), INJECTABLE;INJECTION - 25MG/10ML (2.5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, INJECTABLE;INTRAVENOUS - 40MG/200ML (0.2MG/ML)

INJECTABLE;INTRAVENOUS - 20MG/200ML (0.1MG/ML)
INJECTABLE;INJECTION - 25MG/10ML (2.5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
INJECTABLE;INTRAVENOUS - 40MG/200ML (0.2MG/ML)

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Suppliers, 28 Roquette, 11 BASF, 8 Sigachi Industries, 7 Gangwal Healthcare, 7 Microlex e.U, 6 Gangwal Chemicals, 6 Kerry, 6 SPI Pharma, 5 Ideal Cures Pvt Ltd, 4 ACG Worldwide, 4 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 3 Lonza Capsugel, 3 Corel Pharma Chem, 2 Prachin Chemical, 2 Ingredion Pharma Solutions, 2 Vasa Pharmachem, 2 Nanjing Well Pharmaceutical, 2 Seppic, 2 Actylis, 2 DFE Pharma, 1 DKSH, 1 Finar, 1 Zhejiang Huakang Pharmaceutical, 1 Evonik, 1 Alcedo Pharmachem, 1 Qualicaps, 1 Rochem International Inc, 1 Shijiazhuang Huaxu Pharmaceutical, 1 Pharmatrans-Sanaq

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Also known as: 54527-84-3, Nicardipine hcl, Cardene, Perdipine, Loxen, Nicodel

Molecular Formula

C₂₆H₃₀ClN₃O₆

Molecular Weight

516.0 g/mol

InChI Key

AIKVCUNQWYTVTO-UHFFFAOYSA-N

FDA UNII

K5BC5011K3

A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.

1 2D Structure

Nicardipine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydrochloride

2.1.2 InChI

InChI=1S/C26H29N3O6.ClH/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19;/h5-12,15,24,27H,13-14,16H2,1-4H3;1H

2.1.3 InChI Key

AIKVCUNQWYTVTO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C(C(=C(N1)C)C(=O)OCCN(C)CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OC.Cl

2.2 Other Identifiers

2.2.1 UNII

K5BC5011K3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Antagonil

2. Cardene

3. Cardene I.v.

4. Cardene Sr

5. Dagan

6. Flusemide

7. Hydrochloride, Nicardipine

8. La, Nicardipine

9. Lecibral

10. Lincil

11. Loxen

12. Lucenfal

13. Nicardipine

14. Nicardipine La

15. Nicardipino Ratiopharm

16. Nicardipino Seid

17. Perdipine

18. Ridene

19. Vasonase

20. Y 93

21. Y-93

22. Y93

2.3.2 Depositor-Supplied Synonyms

1. 54527-84-3

2. Nicardipine Hcl

3. Cardene

4. Perdipine

5. Loxen

6. Nicodel

7. Perdipina

8. Yc-93

9. Nicardipine (hydrochloride)

10. Dagan

11. Lecibral

12. Vasonase

13. Ridene

14. Yc-93 Hydrochloride

15. Nicardipinehydrochloride

16. Barizin

17. Cardepine

18. Dacarel

19. Lecibra

20. Lescodil

21. Nerdipina

22. Nicapress

23. Nicardal

24. Nicarpin

25. Nimicor

26. Rycarden

27. Vasodin

28. Nicant

29. Ranvil

30. Rydene

31. Rs-69216

32. Rs-69216-xx-07-0

33. Nsc-757855

34. Mls000069782

35. 2-(benzylmethylamino)ethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylatemonohydrochloride

36. Lincil

37. K5bc5011k3

38. Cardene Sr

39. 2-(benzylmethylamino)ethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate Monohydrochloride

40. 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Hydrochloride

41. Rs-69216xx07-0

42. Angioglebil

43. Bionicard

44. Nicardil

45. Smr000058487

46. Dafil

47. Cardene (tn)

48. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, Methyl 2-(methyl(phenylmethyl)amino)ethyl Ester, Monohydrochloride

49. 3-(2-(benzyl(methyl)amino)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Hydrochloride

50. 5-o-[2-[benzyl(methyl)amino]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydrochloride

51. Yc 93

52. Sr-01000075333

53. Einecs 259-198-4

54. Nicardipine Hydrochloride [usan:jan]

55. Nerdipine

56. Unii-k5bc5011k3

57. Ccris 8508

58. 69441-18-5

59. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-methyl 5-(2-(methyl(phenylmethyl)amino)ethyl) Ester, Hydrochloride (1:1)

60. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-methyl 5-[2-[methyl(phenylmethyl)amino]ethyl] Ester, Hydrochloride (1:1)

61. Prestwick_590

62. Einecs 274-007-4

63. Mfcd00057327

64. Opera_id_357

65. Cardene In 4.8% Dextrose In Plastic Container

66. Cardene In 5.0% Dextrose In Plastic Container

67. Cas-54527-84-3

68. Dsstox_cid_26992

69. Dsstox_rid_82040

70. Dsstox_gsid_46992

71. Schembl41845

72. 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)methyl-2-[methyl(phenylmethyl)amino]-3,5-pyridinedicarboxylic Acid Ethyl Ester Hydrochloride

73. Mls001146898

74. Mls002153279

75. Mls002153794

76. Nicardipine Hydrochloride,(s)

77. Spectrum1501135

78. Chebi:7551

79. Cardene In 0.83% Sodium Chloride In Plastic Container

80. Cardene In 0.86% Sodium Chloride In Plastic Container

81. Chembl1200326

82. Chembl3199626

83. Dtxsid9046992

84. Hms1569m07

85. Hms1921h21

86. Pharmakon1600-01501135

87. Bcp05610

88. Tox21_301832

89. Tox21_500809

90. Ccg-39033

91. Hy-12515a

92. Nsc757855

93. S4181

94. Tn-901

95. Nicardipine Hydrochloride [mi]

96. Akos015994734

97. Bcp9000988

98. Cs-3684

99. Ks-1276

100. Lp00809

101. Nc00578

102. Nicardipine Hydrochloride [jan]

103. Nsc 757855

104. Rs-69216-xx-07-o

105. Nicardipine Hydrochloride (jp17/usan)

106. Nicardipine Hydrochloride [usan]

107. Ncgc00094142-01

108. Ncgc00094142-02

109. Ncgc00094142-03

110. Ncgc00094142-04

111. Ncgc00094142-05

112. Ncgc00256289-01

113. Ncgc00261494-01

114. Nicardipine Hydrochloride [mart.]

115. Nicardipine Hydrochloride [vandf]

116. 2-(benzyl(methyl)amino)ethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate Hydrochloride

117. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-, 2-(benzylmethylamino)ethyl Methyl Ester, Monohydrochloride

118. Ac-36579

119. Nicardipine Hydrochloride [usp-rs]

120. Nicardipine Hydrochloride [who-dd]

121. Nicardipine Hydrochloride, Powder, >=98%

122. Db-052598

123. Eu-0100809

124. Ft-0630671

125. N0635

126. Sw196762-3

127. D00617

128. D91754

129. N 7510

130. Nicardipine Hydrochloride [ep Monograph]

131. Nicardipine Hydrochloride [orange Book]

132. Nicardipine Hydrochloride [usp Monograph]

133. 527n843

134. A830225

135. Sr-01000075333-1

136. Sr-01000075333-5

137. W-105615

138. Q27281986

139. 12-(7-nitrobenzofurazan-4-ylamino)dodecanoicacid

140. Nicardipine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

141. Nicardipine For System Suitability, European Pharmacopoeia (ep) Reference Standard

142. Nicardipine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

143. 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic Acid 3-(2-(n-benzyl-n-methylamino))-ethyl Ester 5-methyl Ester Hydrochloride

144. 2-(n-benzyl-n-methylamino)ethyl Methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Hydrochloride

145. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,?methyl 2-[methyl(phenylmethyl)amino]ethyl Ester, Hydrochloride (1:1)

146. O5-[2-[benzyl(methyl)amino]ethyl] O3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Hydrochloride;nicardipine Hcl

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₀ClN₃O₆
Molecular Weight	516.0 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	10
Exact Mass	515.1823134 g/mol
Monoisotopic Mass	515.1823134 g/mol
Topological Polar Surface Area	114 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	856
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Cardene
Drug Label	Cardene (nicardipine HCI) is a calcium ion influx inhibitor (slow channel blocker or calcium channel blocker). Cardene I.V. for intravenous administration contains 2.5 mg/mL of nicardipine hydrochloride. Nicardipine hydrochloride is a dihydropy...
Active Ingredient	Nicardipine hydrochloride
Dosage Form	Injectable; Capsule
Route	Injection; Oral
Strength	25mg/10ml (2.5mg/ml); 30mg; 20mg
Market Status	Prescription
Company	Chiesi Usa

2 of 6
Drug Name	Cardene sr
Drug Label	CARDENE SR is a sustained release formulation of CARDENE. CARDENE SR capsules for oral administration each contain 30 mg, 45 mg or 60 mg of nicardipine hydrochloride. Nicardipine hydrochloride is a calcium ion influx inhibitor (slow channel block...
Active Ingredient	Nicardipine hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	60mg; 30mg
Market Status	Prescription
Company	Chiesi Usa

3 of 6
Drug Name	Nicardipine hydrochloride
PubMed Health	Nicardipine
Drug Classes	Antianginal, Antihypertensive, Cardiovascular Agent
Drug Label	Nicardipine hydrochloride capsules for oral administration each contain 20 mg or 30 mg of nicardipine hydrochloride. Nicardipine hydrochloride is a calcium ion influx inhibitor (slow channel blocker or calcium channel blocker).Nicardipine hydrochlori...
Active Ingredient	Nicardipine hydrochloride
Dosage Form	Capsule; Injectable
Route	Injection; Oral
Strength	30mg; 25mg/10ml (2.5mg/ml); 20mg
Market Status	Prescription
Company	Exela Pharma Science; Wockhardt; Navinta; Bedford; Ani Pharms; Epic Pharma; Sun Pharma Global; Mylan Institutional; Luitpold; Mylan

4 of 6
Drug Name	Cardene
Drug Label	Cardene (nicardipine HCI) is a calcium ion influx inhibitor (slow channel blocker or calcium channel blocker). Cardene I.V. for intravenous administration contains 2.5 mg/mL of nicardipine hydrochloride. Nicardipine hydrochloride is a dihydropy...
Active Ingredient	Nicardipine hydrochloride
Dosage Form	Injectable; Capsule
Route	Injection; Oral
Strength	25mg/10ml (2.5mg/ml); 30mg; 20mg
Market Status	Prescription
Company	Chiesi Usa

5 of 6
Drug Name	Cardene sr
Drug Label	CARDENE SR is a sustained release formulation of CARDENE. CARDENE SR capsules for oral administration each contain 30 mg, 45 mg or 60 mg of nicardipine hydrochloride. Nicardipine hydrochloride is a calcium ion influx inhibitor (slow channel block...
Active Ingredient	Nicardipine hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	60mg; 30mg
Market Status	Prescription
Company	Chiesi Usa

6 of 6
Drug Name	Nicardipine hydrochloride
PubMed Health	Nicardipine
Drug Classes	Antianginal, Antihypertensive, Cardiovascular Agent
Drug Label	Nicardipine hydrochloride capsules for oral administration each contain 20 mg or 30 mg of nicardipine hydrochloride. Nicardipine hydrochloride is a calcium ion influx inhibitor (slow channel blocker or calcium channel blocker).Nicardipine hydrochlori...
Active Ingredient	Nicardipine hydrochloride
Dosage Form	Capsule; Injectable
Route	Injection; Oral
Strength	30mg; 25mg/10ml (2.5mg/ml); 20mg
Market Status	Prescription
Company	Exela Pharma Science; Wockhardt; Navinta; Bedford; Ani Pharms; Epic Pharma; Sun Pharma Global; Mylan Institutional; Luitpold; Mylan

5 Pharmacology and Biochemistry

5.1 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.)

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.)

Vasodilator Agents

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

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Cytochrome P450 2C19 Inhibitors [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]; Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]

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