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Nitrendipine

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Synopsis

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Chemistry

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Also known as: 39562-70-4, Bayotensin, Baypress, Nidrel, Deiten, Bay-e-5009

Molecular Formula

C₁₈H₂₀N₂O₆

Molecular Weight

360.4 g/mol

InChI Key

PVHUJELLJLJGLN-UHFFFAOYSA-N

FDA UNII

9B627AW319

A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.

1 2D Structure

Nitrendipine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3

2.1.3 InChI Key

PVHUJELLJLJGLN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCOC(=O)C1=C(NC(=C(C1C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OC)C)C

2.2 Other Identifiers

2.2.1 UNII

9B627AW319

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Balminil

2. Bay E 5009

3. Bayotensin

4. Baypresol

5. Baypress

6. Gericin

7. Jutapress

8. Nidrel

9. Niprina

10. Nitre Abz

11. Nitre Puren

12. Nitre-puren

13. Nitregamma

14. Nitren 1a Pharma

15. Nitren Acis

16. Nitren Lich

17. Nitrend Ksk

18. Nitrendepat

19. Nitrendi Biochemie

20. Nitrendidoc

21. Nitrendimerck

22. Nitrendipin Al

23. Nitrendipin Apogepha

24. Nitrendipin Atid

25. Nitrendipin Basics

26. Nitrendipin Beta

27. Nitrendipin Corax

28. Nitrendipin Heumann

29. Nitrendipin Jenapharm

30. Nitrendipin Lindo

31. Nitrendipin Ratiopharm

32. Nitrendipin Stada

33. Nitrendipin Von Ct

34. Nitrendipin-corax

35. Nitrendipin-ratiopharm

36. Nitrendipincorax

37. Nitrendipino Bayvit

38. Nitrendipino Ratiopharm

39. Nitrendipinratiopharm

40. Nitrensal

41. Nitrepress

42. Nitrepuren

43. Tensogradal

44. Trendinol

45. Vastensium

2.3.2 Depositor-Supplied Synonyms

1. 39562-70-4

2. Bayotensin

3. Baypress

4. Nidrel

5. Deiten

6. Bay-e-5009

7. Nitrendipinum

8. Nitrepin

9. Bay E 5009

10. Nitrendipino

11. Bylotensin

12. 3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

13. Nitrendipinum [inn-latin]

14. Nitrendipino [inn-spanish]

15. 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Ethyl Methyl Ester

16. Chebi:7582

17. Nitrendipin

18. Mfcd00082255

19. Nsc-758466

20. Mls000069349

21. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, Ethyl Methyl Ester

22. 5-o-ethyl 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

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

24. 9b627aw319

25. Ncgc00015713-07

26. Smr000058366

27. Dsstox_cid_3373

28. Dsstox_rid_77001

29. Dsstox_gsid_23373

30. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, Ethyl Methyl Ester, (+/-)-

31. Baylotensin

32. Baypress (tn)

33. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-ethyl 5-methyl Ester

34. Sr-01000075334

35. Einecs 254-513-1

36. Brn 0498823

37. Unii-9b627aw319

38. Nitrendipine,(s)

39. Nitrendipine [usan:inn:ban:jan]

40. Cas-39562-70-4

41. Spectrum_001901

42. Opera_id_928

43. Specplus_000742

44. Prestwick0_000916

45. Prestwick1_000916

46. Prestwick2_000916

47. Prestwick3_000916

48. Spectrum2_001565

49. Spectrum3_000968

50. Spectrum4_001088

51. Spectrum5_001655

52. Nitrendipine [mi]

53. N-144

54. (.+/-.)-nitrendipine

55. Nitrendipine [inn]

56. Nitrendipine [jan]

57. Nitrendipine [usan]

58. (+-)-ethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

59. Ethyl 1,4-dihydro-5-(acetoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridincarboxylat

60. Cbiol_001834

61. Lopac0_000881

62. Oprea1_472855

63. Oprea1_703261

64. Schembl38972

65. Bspbio_000792

66. Bspbio_001399

67. Bspbio_002575

68. Kbiogr_000119

69. Kbiogr_001476

70. Kbioss_000119

71. Kbioss_002432

72. Nitrendipine [mart.]

73. Mls000759400

74. Mls001148149

75. Mls001424133

76. Mls002153303

77. Mls002154060

78. (+/-)-nitrendipine

79. Divk1c_006838

80. Nitrendipine [who-dd]

81. Nitrendipine, >95%, Powder

82. Spectrum1503609

83. Spbio_001470

84. Spbio_002981

85. Bpbio1_000872

86. Gtpl2334

87. Chembl3195219

88. Dtxsid0023373

89. Kbio1_001782

90. Kbio2_000119

91. Kbio2_002426

92. Kbio2_002687

93. Kbio2_004994

94. Kbio2_005255

95. Kbio2_007562

96. Kbio3_000237

97. Kbio3_000238

98. Kbio3_001795

99. Brd6392

100. Nitrendipine (jp17/usan/inn)

101. Bio1_000120

102. Bio1_000609

103. Bio1_001098

104. Bio2_000119

105. Bio2_000599

106. Hms1361f21

107. Hms1570h14

108. Hms1791f21

109. Hms1989f21

110. Hms2051b04

111. Hms2089h15

112. Hms2093g17

113. Hms2097h14

114. Hms2230f04

115. Hms3262b04

116. Hms3266b03

117. Hms3371j07

118. Hms3393b04

119. Hms3402f21

120. Hms3411i14

121. Hms3651f05

122. Hms3675i14

123. Hms3714h14

124. Hms3884h21

125. Nitrendipine [ep Impurity]

126. Pharmakon1600-01503609

127. Nitrendipine [ep Monograph]

128. Bcp07540

129. Brd-6392

130. Hy-b0424

131. Nitrendipine For Peak Identification

132. Tox21_110201

133. Tox21_500881

134. Ac-648

135. Bbl028163

136. Bdbm50237611

137. Ca-212

138. Ccg-39343

139. Nsc758466

140. Stk368903

141. Akos000622913

142. Akos015894921

143. Tox21_110201_1

144. Ccg-100991

145. Db01054

146. Ks-1305

147. Lp00881

148. Nc00241

149. Nsc 758466

150. Sdccgsbi-0050856.p004

151. Idi1_033869

152. Nitrendipine 100 Microg/ml In Methanol

153. Ncgc00015713-04

154. Ncgc00015713-05

155. Ncgc00015713-06

156. Ncgc00015713-08

157. Ncgc00015713-09

158. Ncgc00015713-10

159. Ncgc00015713-11

160. Ncgc00015713-13

161. Ncgc00015713-26

162. Ncgc00024013-02

163. Ncgc00024676-02

164. Ncgc00024676-03

165. Ncgc00024676-04

166. Ncgc00024676-05

167. Ncgc00024676-06

168. Ncgc00024676-07

169. Ncgc00261566-01

170. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, Ethyl Methyl Ester, (+-)-

171. 86052-02-0

172. Sy058769

173. (+/-)-bay-e-5009

174. Sbi-0050856.p003

175. Nitrendipine 100 Microg/ml In Acetonitrile

176. Ab00513962

177. Eu-0100881

178. Ft-0601600

179. N1186

180. S2491

181. Sw219737-1

182. C07713

183. D00629

184. Ab00053154-03

185. Ab00053154_04

186. Ab00053154_05

187. 562n704

188. A824621

189. Q416584

190. Sr-01000075334-1

191. Sr-01000075334-2

192. Sr-01000075334-4

193. Sr-01000075334-6

194. W-106422

195. Brd-a02006392-001-06-5

196. Brd-a02006392-001-09-9

197. Nitrendipine, European Pharmacopoeia (ep) Reference Standard

198. (.+/-.)-ethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

199. 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylic Acid Ethyl Methyl Ester

200. 3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate #

201. 3-ethyl5-methyl2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

202. Ethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

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

204. Methylethyl2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

205. Nitrendipine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

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

207. (+/-)-ethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

208. 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine Dicarboxylic Acid Ethyl Methyl Ester

209. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, Ethyl Methyl Ester, (.+/-.)-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₀N₂O₆
Molecular Weight	360.4 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	360.13213636 g/mol
Monoisotopic Mass	360.13213636 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	661
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 treatment of mild to moderate hypertension

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nitrendipine, 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. Nitrendipine is similar to other peripheral vasodilators. Nitrendipine 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 ATC Code

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA08 - Nitrendipine

5.4 Mechanism of Action

By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, Nitrendipine 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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