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Nimodipine

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SOLUTION;ORAL - 3MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, SOLUTION;ORAL - 6MG/ML

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SOLUTION;ORAL - 6MG/ML

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Chemistry

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Also known as: 66085-59-4, Nimotop, Periplum, Admon, Nimodipino, Nymalize

Molecular Formula

C₂₁H₂₆N₂O₇

Molecular Weight

418.4 g/mol

InChI Key

UIAGMCDKSXEBJQ-UHFFFAOYSA-N

FDA UNII

57WA9QZ5WH

A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.

Nimodipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of nimodipine is as a Calcium Channel Antagonist.

1 2D Structure

Nimodipine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3

2.1.3 InChI Key

UIAGMCDKSXEBJQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

57WA9QZ5WH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Admon

2. Bay E 9736

3. Bayvit, Nimodipino

4. Brainal

5. Calnit

6. E 9736, Bay

7. Hexal, Nimodipin

8. Kenesil

9. Modus

10. Nimodipin Hexal

11. Nimodipin Isis

12. Nimodipin-isis

13. Nimodipino Bayvit

14. Nimotop

15. Nymalize

16. Remontal

2.3.2 Depositor-Supplied Synonyms

1. 66085-59-4

2. Nimotop

3. Periplum

4. Admon

5. Nimodipino

6. Nymalize

7. Bay E 9736

8. Nimodipinum

9. Bay-e 9736

10. Nimodipinum [inn-latin]

11. Nimodipino [inn-spanish]

12. Bay-e-9736

13. Nemotan

14. 3-isopropyl 5-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

15. Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

16. Nimodipine Ap

17. Chebi:7575

18. Nimodipine (nimotop)

19. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-methoxyethyl 1-methylethyl Ester

20. Nsc-758476

21. 57wa9qz5wh

22. Mls000863294

23. 3-o-(2-methoxyethyl) 5-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

24. 3-(2-methoxyethyl) 5-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

25. Ncgc00015714-09

26. Smr000058300

27. Dsstox_cid_3370

28. Dsstox_rid_76998

29. Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

30. Dsstox_gsid_23370

31. 2-methoxyethyl Propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

32. Nimogel

33. Drg-0139

34. Nimotop(tm)

35. 1-methylethyl 2-(methyloxy)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

36. 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic Acid 3-beta-methoxyethyl Ester 5-isopropyl Ester

37. Sr-01000075335

38. Nimotop (tn)

39. Einecs 266-127-0

40. Unii-57wa9qz5wh

41. Brn 0459792

42. Nimovent

43. Nimodipime,(s)

44. Nimodipine [usan:usp:inn:ban]

45. Nymalize (tn)

46. Cas-66085-59-4

47. Mfcd00153848

48. Eg-1961

49. Opera_id_14

50. Spectrum_001880

51. Nimodipine [mi]

52. Specplus_000716

53. Nimodipine (usp/inn)

54. Nimodipine [inn]

55. Nimodipine [jan]

56. Prestwick0_000918

57. Prestwick1_000918

58. Prestwick2_000918

59. Prestwick3_000918

60. Spectrum2_001562

61. Spectrum3_000766

62. Spectrum4_000791

63. Spectrum5_001687

64. Nimodipine [usan]

65. N-149

66. Nimodipine [vandf]

67. Nimodipine [mart.]

68. Nimodipine [usp-rs]

69. Nimodipine [who-dd]

70. (+/-)-nimodipine

71. Cbiol_001832

72. Lopac0_000891

73. Schembl34041

74. Bspbio_000796

75. Bspbio_001397

76. Bspbio_002412

77. Kbiogr_000117

78. Kbiogr_001262

79. Kbioss_000117

80. Kbioss_002408

81. Mls000069381

82. Mls001076550

83. Mls001424155

84. Mls002154061

85. Mls002172461

86. Mls003899190

87. Divk1c_006812

88. Spectrum1503600

89. Spbio_001464

90. Spbio_002985

91. Bpbio1_000876

92. Gtpl2523

93. Chembl3197349

94. Dtxsid5023370

95. Nimodipine [orange Book]

96. Schembl22882841

97. Kbio1_001756

98. Kbio2_000117

99. Kbio2_002403

100. Kbio2_002685

101. Kbio2_004971

102. Kbio2_005253

103. Kbio2_007539

104. Kbio3_000233

105. Kbio3_000234

106. Kbio3_001632

107. 3-isopropyl 5-(2-methoxyethyl)

108. Brd8407

109. Nimodipine [ep Monograph]

110. Nimodipine [usp Impurity]

111. Bio1_000118

112. Bio1_000607

113. Bio1_001096

114. Bio2_000117

115. Bio2_000597

116. Hms1361f19

117. Hms1570h18

118. Hms1791f19

119. Hms1922e04

120. Hms1989f19

121. Hms2052m05

122. Hms2089h13

123. Hms2093g11

124. Hms2097h18

125. Hms2234b05

126. Hms3262d04

127. Hms3266o22

128. Hms3369g07

129. Hms3394m05

130. Hms3402f19

131. Hms3411i12

132. Hms3657i03

133. Hms3675i12

134. Hms3714h18

135. Nimodipine [usp Monograph]

136. Pharmakon1600-01503600

137. 3,5-pyridinecarboxylic Acid 2-methoxyethyl 1-methylethyl Ester

138. Act02628

139. Albb-015317

140. Amy40399

141. Bcp21152

142. Brd-8407

143. Hy-b0265

144. 2,6-dimethyl-4-(3-nitrophenyl)-

145. Tox21_110202

146. Tox21_500891

147. Bbl028286

148. Bdbm50101971

149. Ca-211

150. Ccg-39340

151. Nsc758476

152. S1747

153. Stk642934

154. Akos005174934

155. Akos015852459

156. Nimodipine - Cas 66085-59-4

157. Nimodipine 100 Microg/ml In Methanol

158. Tox21_110202_1

159. Ac-8484

160. Ccg-101085

161. Db00393

162. Ks-1304

163. Lp00891

164. Nc00335

165. Nsc 758476

166. Sdccgsbi-0050866.p004

167. Idi1_033867

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

169. Ncgc00015714-04

170. Ncgc00015714-05

171. Ncgc00015714-06

172. Ncgc00015714-07

173. Ncgc00015714-08

174. Ncgc00015714-10

175. Ncgc00015714-11

176. Ncgc00015714-12

177. Ncgc00015714-13

178. Ncgc00015714-16

179. Ncgc00015714-28

180. Ncgc00021456-02

181. Ncgc00024675-02

182. Ncgc00024675-03

183. Ncgc00024675-04

184. Ncgc00024675-05

185. Ncgc00024675-06

186. Ncgc00024675-07

187. Ncgc00024675-08

188. Ncgc00024675-09

189. Ncgc00261576-01

190. Nimodipine 100 Microg/ml In Acetonitrile

191. O5-isopropyl O3-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

192. Smr002530605

193. Sbi-0050866.p003

194. Ab00513963

195. Eu-0100891

196. Ft-0602600

197. N0896

198. Sw219238-1

199. C07267

200. D00438

201. F20554

202. 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-

203. Ab00053314-03

204. Ab00053314-04

205. Ab00053314_05

206. Ab00053314_06

207. 085n594

208. Q421429

209. Sr-01000075335-1

210. Sr-01000075335-2

211. Sr-01000075335-4

212. Sr-01000075335-5

213. Sr-01000075335-7

214. Brd-a58048407-001-06-3

215. Brd-a58048407-001-09-7

216. Bay E 9736 Pound>> Bay-e-9736 Pound>> Baye97

217. Nimodipine, British Pharmacopoeia (bp) Reference Standard

218. Nimodipine, European Pharmacopoeia (ep) Reference Standard

219. Nimodipine, United States Pharmacopeia (usp) Reference Standard

220. Nimodipine, Pharmaceutical Secondary Standard; Certified Reference Material

221. Nimodipine For Peak Identification, Europepharmacopoeia (ep) Reference Standard

222. 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 2-methyloxyethyl 1-methylethyl Ester

223. 2-methoxyethyl 1-methylethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

224. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-methoxyethyl) 5-(1-methylethyl) Ester

225. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,?2-methoxyethyl 1-methylethyl Ester

226. 3-isopropyl 5-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate #

227. 3-isopropyl5-(2-methoxyethyl)2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

228. Isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

229. O5-(2-methoxyethyl) O3-propan-2-yl 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	C₂₁H₂₆N₂O₇
Molecular Weight	418.4 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	418.17400117 g/mol
Monoisotopic Mass	418.17400117 g/mol
Topological Polar Surface Area	120 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	736
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	Nimodipine
PubMed Health	Nimodipine (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Nimodipine belongs to the class of pharmacological agents known as calcium channel blockers. Nimodipine is isopropyl 2 - methoxyethyl 1, 4 - dihydro - 2, 6 - dimethyl - 4 - (m-nitrophenyl) - 3, 5 pyridinedicarboxylate.It has a molecular weight...
Active Ingredient	Nimodipine
Dosage Form	Capsule
Route	Oral
Strength	30mg
Market Status	Prescription
Company	Thepharmanetwork; Sun Pharm Inds; Barr Labs; Banner Pharmacaps

2 of 4
Drug Name	Nymalize
PubMed Health	Nimodipine (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	NYMALIZE contains nimodipine, a dihydropyridine calcium channel blocker. Nimodipine is isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate. It has a molecular weight of 418.5 and a molecular formula of C21H26...
Active Ingredient	Nimodipine
Dosage Form	Solution
Route	Oral
Strength	60mg/20ml
Market Status	Prescription
Company	Arbor Pharms

3 of 4
Drug Name	Nimodipine
PubMed Health	Nimodipine (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Nimodipine belongs to the class of pharmacological agents known as calcium channel blockers. Nimodipine is isopropyl 2 - methoxyethyl 1, 4 - dihydro - 2, 6 - dimethyl - 4 - (m-nitrophenyl) - 3, 5 pyridinedicarboxylate.It has a molecular weight...
Active Ingredient	Nimodipine
Dosage Form	Capsule
Route	Oral
Strength	30mg
Market Status	Prescription
Company	Thepharmanetwork; Sun Pharm Inds; Barr Labs; Banner Pharmacaps

4 of 4
Drug Name	Nymalize
PubMed Health	Nimodipine (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	NYMALIZE contains nimodipine, a dihydropyridine calcium channel blocker. Nimodipine is isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate. It has a molecular weight of 418.5 and a molecular formula of C21H26...
Active Ingredient	Nimodipine
Dosage Form	Solution
Route	Oral
Strength	60mg/20ml
Market Status	Prescription
Company	Arbor Pharms

4.2 Drug Indication

For use as an adjunct to improve neurologic outcome following subarachnoid hemorrhage (SAH) from ruptured intracranial berry aneurysms by reducing the incidence and severity of ischemic deficits.

FDA Label

Treatment of aneurysmal subarchnoidal haemorrhage

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nimodipine belongs to the class of pharmacological agents known as calcium channel blockers. Nimodipine is indicated for the improvement of neurological outcome by reducing the incidence and severity of ischemic deficits in patients with subarachnoid hemorrhage from ruptured congenital aneurysms who are in good neurological condition post-ictus (e.g., Hunt and Hess Grades I-III). The contractile processes of smooth muscle cells are dependent upon calcium ions, which enter these cells during depolarization as slow ionic transmembrane currents. Nimodipine inhibits calcium ion transfer into these cells and thus inhibits contractions of vascular smooth muscle. In animal experiments, nimodipine had a greater effect on cerebral arteries than on arteries elsewhere in the body perhaps because it is highly lipophilic, allowing it to cross the blood brain barrier.

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.)

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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

NIMODIPINE

5.3.2 FDA UNII

57WA9QZ5WH

5.3.3 Pharmacological Classes

Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]

5.4 ATC Code

C08CA06

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA06 - Nimodipine

5.5 Absorption, Distribution and Excretion

Absorption

In humans, nimodipine is rapidly absorbed after oral administration, and peak concentrations are generally attained within one hour. Bioavailability is 100% following intravenous administration and 3-30% following oral administration due to extensive first-pass metabolism.

Route of Elimination

Nimodipine is eliminated almost exclusively in the form of metabolites and less than 1% is recovered in the urine as unchanged drug. Numerous metabolites, all of which are either inactive or considerably less active than the parent compound, have been identified.

5.6 Metabolism/Metabolites

Hepatic metabolism via CYP 3A4.

Nimodipine has known human metabolites that include 2,6-Dimethyl-4-(3-nitrophenyl)-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid, Dehydro nimodipine, and Unii-96S4GG1upr.

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

5.7 Biological Half-Life

1.7-9 hours

5.8 Mechanism of Action

Although the precise mechanism of action is not known, nimodipine blocks intracellular influx of calcium through voltage-dependent and receptor-operated slow calcium channels across the membranes of myocardial, vascular smooth muscle, and neuronal cells. By specifically binding to L-type voltage-gated calcium channels, nimodipine inhibits the calcium ion transfer, resulting in the inhibition of vascular smooth muscle contraction. Evidence suggests that the dilation of small cerebral resistance vessels, with a resultant increase in collateral circulation, and/or a direct effect involving the prevention of calcium overload in neurons may be responsible for nimodipine's clinical effect in patients with subarachnoid hemorrhage.

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

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Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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DOSAGE - SOLUTION;ORAL - 3MG/ML **Federal Reg...DOSAGE - SOLUTION;ORAL - 3MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 203340

DOSAGE - SOLUTION;ORAL - 6MG/ML

USFDA APPLICATION NUMBER - 203340

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Nimodipine

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

13 API Suppliers

8 USDMF

4 CEP/COS

1 EU WC

1 KDMF

7 NDC API

7 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

14 Drugs in Development

INTERMEDIATES

2 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

53 FDF Dossiers

11 FDA Orange Book

31 Europe

1 Canada

2 South Africa

8 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

SOLUTION;ORAL - 3MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

SOLUTION;ORAL - 6MG/ML

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2 Rochem International Inc

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7 DKSH

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4 ACG Worldwide

5 Actylis

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14 Roquette

7 Seppic

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1 Sigachi Industries

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EXCIPIENTS BY APPLICATIONS

46 Coating Systems & Additives

28 Fillers, Diluents & Binders

21 Controlled & Modified Release

18 Film Formers & Plasticizers

14 Taste Masking

13 Topical

13 Parenteral

12 Thickeners and Stabilizers

12 Chewable & Orodispersible Aids

11 Direct Compression

9 Empty Capsules

8 Solubilizers

6 Granulation

5 Co-Processed Excipients

SOLUTION;ORAL - 3MG/ML Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons