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    Chemistry

    Click the arrow to open the dropdown
    read-moreClick the button for full data set
    read-moreClick the button for full data set
    Also known as: 21829-25-4, Adalat, Procardia, Procardia xl, Adalat cc, Cordipin
    Molecular Formula
    C17H18N2O6
    Molecular Weight
    346.3  g/mol
    InChI Key
    HYIMSNHJOBLJNT-UHFFFAOYSA-N
    FDA UNII
    I9ZF7L6G2L
    Nifedipine
    A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.
    Nifedipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of nifedipine is as a Calcium Channel Antagonist.
    1 2D Structure

    Nifedipine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
    2.1.2 InChI
    InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3
    2.1.3 InChI Key
    HYIMSNHJOBLJNT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
    2.2 Other Identifiers
    2.2.1 UNII
    I9ZF7L6G2L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Adalat

    2. Bay 1040

    3. Bay A 1040

    4. Bay-1040

    5. Bay-a-1040

    6. Bay1040

    7. Baya1040

    8. Cordipin

    9. Cordipine

    10. Corinfar

    11. Fenigidin

    12. Korinfar

    13. Monohydrochloride, Nifedipine

    14. Nifangin

    15. Nifedipine Gtis

    16. Nifedipine Monohydrochloride

    17. Nifedipine-gtis

    18. Procardia

    19. Procardia Xl

    20. Vascard

    2.3.2 Depositor-Supplied Synonyms

    1. 21829-25-4

    2. Adalat

    3. Procardia

    4. Procardia Xl

    5. Adalat Cc

    6. Cordipin

    7. Corinfar

    8. Fenihidine

    9. Citilat

    10. Oxcord

    11. Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

    12. Bay-a-1040

    13. Coracten

    14. Fenihidin

    15. Afeditab Cr

    16. Adalate

    17. Nifediac

    18. Hexadilat

    19. Introcar

    20. Kordafen

    21. Nifedical

    22. Nifedipinum

    23. Tibricol

    24. Adapine

    25. Anifed

    26. Pidilat

    27. Sepamit

    28. Zenusin

    29. Orix

    30. Adalat La

    31. Bay A 1040

    32. Nifedipino

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

    34. Adipine Xl

    35. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, Dimethyl Ester

    36. C17h18n2o6

    37. Mfcd00057326

    38. Nifedipine (adalat)

    39. Ccris 6074

    40. Chebi:7565

    41. Nifedipine Slow Release

    42. 3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

    43. Chembl193

    44. Nsc-757242

    45. I9zf7l6g2l

    46. Mls000028521

    47. Dimethyl 1,4-dihydro-2,6-dimethyl-4-(2'-nitrophenyl)-3,5-pyridinedicarboxylate

    48. Dimethyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate

    49. Ncgc00015748-11

    50. Chronadalate

    51. Dignokonstant

    52. Adapress

    53. Afeditab

    54. Aldipin

    55. Alfadal

    56. Angipec

    57. Aprical

    58. Bonacid

    59. Calcibloc

    60. Calcigard

    61. Calcilat

    62. Cardifen

    63. Cardilat

    64. Cardionorm

    65. Cordafen

    66. Cordaflex

    67. Cordalat

    68. Cordicant

    69. Cordilan

    70. Corotrend

    71. Corynphar

    72. Dilafed

    73. Dipinkor

    74. Duranifin

    75. Ecodipi

    76. Ecodipin

    77. Fenamon

    78. Hadipin

    79. Macorel

    80. Megalat

    81. Myogard

    82. Nifecard

    83. Nifecor

    84. Nifedicor

    85. Nifedin

    86. Nifedipres

    87. Nifelan

    88. Nifelat

    89. Nificard

    90. Smr000058291

    91. Alonix

    92. Anpine

    93. Camont

    94. Fedcor

    95. Glopir

    96. Coral

    97. Depin

    98. Alat

    99. Adalat Retard

    100. Cas-21829-25-4

    101. Fedcor Retard

    102. Adalat Crono

    103. Chronadalate Lp

    104. Adalat Oros

    105. 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbomethoxy-1,4-dihydropyridine

    106. Dsstox_cid_5715

    107. Ecodipin E

    108. Apo-nifed

    109. Nifensar Xl

    110. Alonix S

    111. Fenamon Sr

    112. Dimethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate

    113. Adalat Cr

    114. Adalat Ft

    115. Adalat Lp

    116. Adalat Pa

    117. Adalat Gits

    118. Dsstox_rid_77889

    119. Adalat 5

    120. Dsstox_gsid_25715

    121. Adalat 10

    122. Adalat 20

    123. Adalat Gits 30

    124. Alpha-nifedipine Retard

    125. Emaberin

    126. Dilcor

    127. Aprical Long

    128. Slofedipine Xl

    129. Fortipine La

    130. Nifedical Xl

    131. Nifedipinum [inn-latin]

    132. Tensipine Mr

    133. 4-(2-nitrophenyl)-2,6-dimethyl-3,5-dicarbomethoxy-1,4-dihydropyridine

    134. Adalate Lp

    135. Nifedipino [inn-spanish]

    136. Adalat Xl

    137. 4-(2'-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsaeuredimethylester

    138. Dimethyl 4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    139. Procardia (tn)

    140. 193689-82-6

    141. Adalat (tn)

    142. Afeditab Cr (tn)

    143. 1173023-46-5

    144. Sr-01000075332

    145. Baya1040

    146. Nifedipine,(s)

    147. Bay 1040

    148. Kb-1712p

    149. Prestwick_357

    150. Einecs 244-598-3

    151. Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate

    152. Brn 0497773

    153. Nifedipine-[13c8]

    154. Spectrum_000979

    155. Tocris-1075

    156. Nifedipine [mi]

    157. Nifedipine [inn]

    158. Nifedipine [jan]

    159. Opera_id_1816

    160. Prestwick0_000063

    161. Prestwick1_000063

    162. Prestwick2_000063

    163. Prestwick3_000063

    164. Spectrum2_001058

    165. Spectrum3_000516

    166. Spectrum4_000074

    167. Spectrum5_001278

    168. Lopac-n-7634

    169. Nifedipine [hsdb]

    170. Nifedipine [inci]

    171. Nifedipine [usan]

    172. Nifedipine [vandf]

    173. Unii-i9zf7l6g2l

    174. N 7634

    175. Cid_4485

    176. Nifedipine [mart.]

    177. Schembl3968

    178. Nifedipine [usp-rs]

    179. Nifedipine [who-dd]

    180. Nifedipine [who-ip]

    181. Bidd:pxr0034

    182. Cbiol_001826

    183. Lopac0_000819

    184. Oprea1_788617

    185. Bspbio_000245

    186. Bspbio_001391

    187. Bspbio_002071

    188. Kbiogr_000111

    189. Kbiogr_000627

    190. Kbiogr_002400

    191. Kbioss_000111

    192. Kbioss_001459

    193. Kbioss_002405

    194. Mls000758222

    195. Mls001148146

    196. Mls001401371

    197. Bidd:gt0442

    198. Divk1c_000313

    199. Spectrum1500431

    200. Spbio_001016

    201. Spbio_002166

    202. Bpbio1_000271

    203. Gtpl2514

    204. Nifedipine (jp17/usp/inn)

    205. Bay-a 1040

    206. Dtxsid2025715

    207. Nifedipine [orange Book]

    208. Bcbcmap01_000046

    209. Hms500p15

    210. Hsdb 7775

    211. Kbio1_000313

    212. Kbio2_000111

    213. Kbio2_001459

    214. Kbio2_002400

    215. Kbio2_002679

    216. Kbio2_004027

    217. Kbio2_004968

    218. Kbio2_005247

    219. Kbio2_006595

    220. Kbio2_007536

    221. Kbio3_000221

    222. Kbio3_000222

    223. Kbio3_001571

    224. Kbio3_002879

    225. Nifedipine [ep Monograph]

    226. Nifedipine [usp Impurity]

    227. Cmap_000042

    228. Nifedipine-d4(2-nitrophenyl-d4)

    229. Ninds_000313

    230. Bio1_000112

    231. Bio1_000601

    232. Bio1_001090

    233. Bio2_000111

    234. Bio2_000591

    235. Hms1361f13

    236. Hms1568m07

    237. Hms1791f13

    238. Hms1920p19

    239. Hms1989f13

    240. Hms2051o03

    241. Hms2089h11

    242. Hms2091h20

    243. Hms2095m07

    244. Hms2233b22

    245. Hms3262d19

    246. Hms3267g06

    247. Hms3393o03

    248. Hms3412e17

    249. Hms3651m19

    250. Hms3676e17

    251. Hms3712m07

    252. Hms3748o21

    253. Nifedipine [usp Monograph]

    254. Pharmakon1600-01500431

    255. Nifedipinum [who-ip Latin]

    256. Act02669

    257. Bcp21147

    258. Hy-b0284

    259. L-type Calcium Channel Blocker Iii

    260. Tox21_110212

    261. Tox21_200304

    262. Tox21_500819

    263. Bbl023163

    264. Bdbm50000778

    265. Bdbm50101817

    266. Ccg-40115

    267. Nsc757242

    268. Nsc786036

    269. S1808

    270. Stk735567

    271. Zinc85205448

    272. Akos002942507

    273. Akos037515769

    274. Nifedipine - Cas 21829-25-4

    275. Nifedipine 100 Microg/ml In Methanol

    276. Nifedipine, >=98% (hplc), Powder

    277. Tox21_110212_1

    278. Ac-8061

    279. Ccg-100758

    280. Db01115

    281. Ks-1456

    282. Lp00819

    283. Nc00008

    284. Nifedipine [usan:usp:inn:ban:jan]

    285. Nsc 757242

    286. Nsc-786036

    287. Sdccgsbi-0050796.p005

    288. 4-(2'-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsaeuredimethylester [german]

    289. Idi1_000313

    290. Idi1_033861

    291. Bay-1040;bay 1040;bay1040

    292. Ncgc00015748-01

    293. Ncgc00015748-02

    294. Ncgc00015748-03

    295. Ncgc00015748-04

    296. Ncgc00015748-05

    297. Ncgc00015748-06

    298. Ncgc00015748-07

    299. Ncgc00015748-08

    300. Ncgc00015748-09

    301. Ncgc00015748-10

    302. Ncgc00015748-12

    303. Ncgc00015748-13

    304. Ncgc00015748-14

    305. Ncgc00015748-15

    306. Ncgc00015748-17

    307. Ncgc00015748-33

    308. Ncgc00021710-02

    309. Ncgc00024983-01

    310. Ncgc00024983-02

    311. Ncgc00024983-03

    312. Ncgc00024983-04

    313. Ncgc00024983-05

    314. Ncgc00024983-06

    315. Ncgc00024983-07

    316. Ncgc00024983-08

    317. Ncgc00091707-01

    318. Ncgc00091707-02

    319. Ncgc00091707-03

    320. Ncgc00257858-01

    321. Ncgc00261504-01

    322. Bn166183

    323. Cpd000058291

    324. Sy074220

    325. Sbi-0050796.p004

    326. Eu-0100819

    327. Ft-0630478

    328. Ft-0653833

    329. Ft-0672727

    330. N0528

    331. Sw219724-1

    332. 29n254

    333. Bim-0050796.0001

    334. C07266

    335. D00437

    336. Q39111

    337. Ab00052051-05

    338. Ab00052051_06

    339. Ab00052051_07

    340. 5-22-04-00268 (beilstein Handbook Reference)

    341. A899873

    342. L001054

    343. Q-201471

    344. Sr-01000075332-1

    345. Sr-01000075332-3

    346. Sr-01000075332-4

    347. Sr-01000075332-6

    348. Brd-k96354014-001-01-3

    349. Brd-k96354014-001-10-4

    350. Z90350374

    351. F2173-0802

    352. Nifedipine, British Pharmacopoeia (bp) Reference Standard

    353. Nifedipine, European Pharmacopoeia (ep) Reference Standard

    354. Nifedipine, United States Pharmacopeia (usp) Reference Standard

    355. 2,6-dimethyl-3,5-dicarbomethoxy-4-(2-nitrophenyl)-1,4-dihydropyridine

    356. 4-(2'-nitrophenyl)-2,6 Dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine

    357. 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine

    358. Nifedipine, Pharmaceutical Secondary Standard; Certified Reference Material

    359. 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylicaciddimethylester

    360. 2,6-dimethyl-4-(2nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic Acid 3,5-dimethyl Ester

    361. Dimethyl (4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate)

    362. Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate #

    363. Dimethyl2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

    364. 101539-70-2

    365. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, Dimethyl Ester (9ci)

    366. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-, Dimethyl Ester (8ci)

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 346.3 g/mol
    Molecular Formula C17H18N2O6
    XLogP32.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count5
    Exact Mass346.11648630 g/mol
    Monoisotopic Mass346.11648630 g/mol
    Topological Polar Surface Area110 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity608
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 10  
    Drug NameAdalat cc
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelAdalat CC is an extended release tablet dosage form of the calcium channel blocker nifedipine. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-dimethyl ester, C17H18N2O6, and has the structural formula:Nifedi...
    Active IngredientNifedipine
    Dosage FormTablet, extended release
    RouteOral
    Strength60mg; 30mg; 90mg
    Market StatusPrescription
    CompanyBayer Hlthcare

    2 of 10  
    Drug NameAfeditab cr
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelAfeditab CR is an extended release tablet dosage form of the calcium channel blocker nifedipine. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2- nitrophenyl)-dimethyl ester, C H N O , and has the structural formula: 1718...
    Active IngredientNifedipine
    Dosage FormTablet, extended release
    RouteOral
    Strength60mg; 30mg
    Market StatusPrescription
    CompanyWatson Labs

    3 of 10  
    Drug NameNifedipine
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelNifedipine is a drug belonging to a class of pharmacological agents known as the calcium channel blockers. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, C17H18N2O6, and has the structural fo...
    Active IngredientNifedipine
    Dosage FormTablet, extended release; Capsule
    Routeoral; Oral
    Strength30mg; 90mg; 60mg; 10mg; 20mg
    Market StatusPrescription
    CompanyTwi Pharms; Valeant Intl; Osmotica Pharm; Par Pharm; Intergel Pharm; Matrix Labs; Actavis Elizabeth; Martec Usa; Emcure Pharms Usa; Mylan

    4 of 10  
    Drug NameProcardia
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelPROCARDIA (nifedipine) is an antianginal drug belonging to a class of pharmacological agents, the calcium channel blockers. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, C17H18N2O6, and ha...
    Active IngredientNifedipine
    Dosage FormCapsule
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyPfizer

    5 of 10  
    Drug NameProcardia xl
    Drug LabelNifedipine is a drug belonging to a class of pharmacological agents known as the calcium channel blockers. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, C17H18N2O6, and has the structural fo...
    Active IngredientNifedipine
    Dosage FormTablet, extended release
    RouteOral
    Strength30mg; 90mg; 60mg
    Market StatusPrescription
    CompanyPfizer

    6 of 10  
    Drug NameAdalat cc
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelAdalat CC is an extended release tablet dosage form of the calcium channel blocker nifedipine. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-dimethyl ester, C17H18N2O6, and has the structural formula:Nifedi...
    Active IngredientNifedipine
    Dosage FormTablet, extended release
    RouteOral
    Strength60mg; 30mg; 90mg
    Market StatusPrescription
    CompanyBayer Hlthcare

    7 of 10  
    Drug NameAfeditab cr
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelAfeditab CR is an extended release tablet dosage form of the calcium channel blocker nifedipine. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2- nitrophenyl)-dimethyl ester, C H N O , and has the structural formula: 1718...
    Active IngredientNifedipine
    Dosage FormTablet, extended release
    RouteOral
    Strength60mg; 30mg
    Market StatusPrescription
    CompanyWatson Labs

    8 of 10  
    Drug NameNifedipine
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelNifedipine is a drug belonging to a class of pharmacological agents known as the calcium channel blockers. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, C17H18N2O6, and has the structural fo...
    Active IngredientNifedipine
    Dosage FormTablet, extended release; Capsule
    Routeoral; Oral
    Strength30mg; 90mg; 60mg; 10mg; 20mg
    Market StatusPrescription
    CompanyTwi Pharms; Valeant Intl; Osmotica Pharm; Par Pharm; Intergel Pharm; Matrix Labs; Actavis Elizabeth; Martec Usa; Emcure Pharms Usa; Mylan

    9 of 10  
    Drug NameProcardia
    PubMed HealthNifedipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Antimigraine, Cardiovascular Agent
    Drug LabelPROCARDIA (nifedipine) is an antianginal drug belonging to a class of pharmacological agents, the calcium channel blockers. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, C17H18N2O6, and ha...
    Active IngredientNifedipine
    Dosage FormCapsule
    RouteOral
    Strength10mg
    Market StatusPrescription
    CompanyPfizer

    10 of 10  
    Drug NameProcardia xl
    Drug LabelNifedipine is a drug belonging to a class of pharmacological agents known as the calcium channel blockers. Nifedipine is 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, C17H18N2O6, and has the structural fo...
    Active IngredientNifedipine
    Dosage FormTablet, extended release
    RouteOral
    Strength30mg; 90mg; 60mg
    Market StatusPrescription
    CompanyPfizer

    4.2 Therapeutic Uses

    Calcium Channel Blockers; Tocolytic Agents; Vasodilator Agents

    National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

    Nifedipine extended-release tablets are indicated for the management of vasospastic angina confirmed by any of the following criteria: 1) classical pattern of angina at rest accompanied by ST segment elevation, 2) angina or coronary artery spasm provoked by ergonovine, or 3) angiographically demonstrated coronary artery spasm. In those patients who have had angiography, the presence of significant fixed obstructive disease is not incompatible with the diagnosis of vasospastic angina, provided that the above criteria are satisfied. Nifedipine extended-release may also be used where the clinical presentation suggests a possible vasospastic component but where vasospasm has not been confirmed, eg, where pain has a variable threshold on exertion or in unstable angina where electrocardiographic findings are compatible with intermittent vasospasm, or when angina is refractory to nitrates and/or adequate doses of beta blockers. /Included in US product label/

    US Natl Inst Health; DailyMed. Current Medication Information for Nifedipine (nifedipine) tablet, film coated, extended release (May 2006). Available from, as of October 15, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1158

    Nifedipine extended-release tablets are indicated for the management of chronic stable angina (effort-associated angina) without evidence of vasospasm in patients who remain symptomatic despite adequate doses of beta blockers and/or organic nitrates or who cannot tolerate those agents. /Included in US product label/

    US Natl Inst Health; DailyMed. Current Medication Information for Nifedipine (nifedipine) tablet, film coated, extended release (May 2006). Available from, as of October 15, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1158

    Nifedipine extended-release tablets (ADALAT CC) is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents. /Included in US product label/

    US Natl Inst Health; DailyMed. Current Medication Information for ADALAT CC (nifedipine) tablet, film coated (June 2009). Available from, as of October 15, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10098

    4.3 Drug Warning

    The National Heart, Lung, and Blood Institute (NHLBI) concluded from the apparent concordance of findings from observational studies in hypertensive patients and from randomized studies principally in acute myocardial infarction and unstable angina patients that it seems prudent and consistent with current evidence to recommend that short-acting nifedipine, especially at high doses, be used in the management of hypertension, angina, or myocardial infarction with great caution, if at all.

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    The Antihypertensive and Lipid-Lowering Treatment to Prevent Heart Attack Trial (ALLHAT), which compared long-term therapy with an ACE inhibitor (lisinopril) or dihydropyridine-derivative calcium-channel blocker (amlodipine) revealed no difference in the primary outcome of combined fatal coronary heart disease or nonfatal myocardial infarction among these therapies.

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    Serious adverse reactions requiring discontinuance of nifedipine therapy or dosage adjustment are relatively rare. An increase in the frequency, intensity, and duration of angina, possibly resulting from hypotension, has occurred rarely during initiation of nifedipine therapy. Additional serious adverse effects including myocardial infarction, congestive heart failure or pulmonary edema, and ventricular arrhythmia or conduction defects have reportedly occurred in 4%, 2%, and less than 0.5% of patients receiving conventional nifedipine capsules, respectively, but these have not been directly attributed to the drug.

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    Rarely, patients, usually receiving a beta blocker, have developed heart failure after beginning nifedipine. Patients with tight aortic stenosis may be at greater risk for such an event, as the unloading effect of nifedipine would be expected to be of less benefit to those patients, owing to their fixed impedance to flow across the aortic valve.

    US Natl Inst Health; DailyMed. Current Medication Information for Nifedipine (nifedipine) tablet, film coated, extended release (May 2006). Available from, as of October 15, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1158

    For more Drug Warnings (Complete) data for Nifedipine (32 total), please visit the HSDB record page.

    4.4 Drug Indication

    Nifedipine capsules are indicated to treat vasospastic angina and chronic stable angina. Extended release tablets are indicated to treat vasospastic angina, chronic stable angina, and hypertension.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Nifedipine is an inhibitor of L-type voltage gated calcium channels that reduces blood pressure and increases oxygen supply to the heart. Immediate release nifedipine's duration of action requires dosing 3 times daily. Nifedipine dosing is generally 10-120mg daily. Patients should be counselled regarding the risk of excessive hypotension, angina, and myocardial infarction.

    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.)

    Tocolytic Agents

    Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete. (See all compounds classified as Tocolytic Agents.)

    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
    NIFEDIPINE
    5.3.2 FDA UNII
    I9ZF7L6G2L
    5.3.3 Pharmacological Classes
    Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]
    5.4 ATC Code

    C08CA05

    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

    C08CA05 - Nifedipine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Sublingual dosing leads to a Cmax of 10ng/mL, with a Tmax of 50min, and an AUC of 25ng\*h/mL. Oral dosing leads to a Cmax of 82ng/mL, with a Tmax of 28min, and an AUC of 152ng\*h/mL. Nifedipine is a Biopharmaceutics Classification System Class II drug, meaning it has low solubility and high intestinal permeability. It is almost completely absorbed in the gastrointestinal tract but has a bioavilability of 45-68%, partly due to first pass metabolism.

    Route of Elimination

    Nifedipine is 60-80% recovered in the urine as inactive water soluble metabolites, and the rest is eliminated in the feces as metabolites.

    Volume of Distribution

    The steady state volume of distribution of nifedipine is 0.62-0.77L/kg and the volume of distribution of the central compartment is 0.25-0.29L/kg.

    Clearance

    The total body clearance of nifedipine is 450-700mL/min.

    Approximately 90% of an oral dose of nifedipine is rapidly absorbed from the GI tract following oral administration of the drug as conventional capsules. Only about 45-75% of an oral dose as conventional capsules reaches systemic circulation as unchanged drug since nifedipine is metabolized on first pass through the liver. Peak serum concentrations usually are reached within 0.5-2 hours after oral administration as conventional capsules. Food appears to decrease the rate but not the extent of absorption of nifedipine as conventional capsules.

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    Plasma drug concentrations rise at a gradual, controlled rate after a nifedipine extended-release tablet dose and reach a plateau at approximately six hours after the first dose. For subsequent doses, relatively constant plasma concentrations at this plateau are maintained with minimal fluctuations over the 24-hour dosing interval. About a four-fold higher fluctuation index (ratio of peak to trough plasma concentration) was observed with the conventional immediate-release nifedipine capsule at t.i.d. dosing than with once daily nifedipine extended-release tablet.

    US Natl Inst Health; DailyMed. Current Medication Information for Nifedipine (nifedipine) tablet, film coated, extended release (May 2006). Available from, as of October 15, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1158

    At steady-state the bioavailability of the nifedipine extended-release tablet is 86% relative to immediate-release nifedipine capsules. Administration of the nifedipine extended-release tablet in the presence of food slightly alters the early rate of drug absorption, but does not influence the extent of drug bioavailability. Markedly reduced GI retention time over prolonged periods (ie, short bowel syndrome), however, may influence the pharmacokinetic profile of the drug which could potentially result in lower plasma concentrations.

    US Natl Inst Health; DailyMed. Current Medication Information for Nifedipine (nifedipine) tablet, film coated, extended release (May 2006). Available from, as of October 15, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1158

    The manufacturer states that relative oral bioavailability differs little if conventional nifedipine capsules are swallowed intact, bitten and swallowed, or bitten and held sublingually. However, some data indicate that the rate and extent of absorption of nifedipine following sublingual administration may be decreased substantially. Oral bioavailability of nifedipine may be increased up to twofold in patients with liver cirrhosis.

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    For more Absorption, Distribution and Excretion (Complete) data for Nifedipine (10 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Nifedipine is predominantly metabolized by CYP3A4. Nifedipine is predominantly metabolized to 2,6-dimethyl-4-(2-nitrophenyl)-5-methoxycarbonyl-pyridine-3-carboxylic acid, and then further metabolized to 2-hydroxymethyl-pyridine carboxylic acid. Nifedipine is also minorly metabolized to dehydronifedipine.

    The drug is extensively metabolized in the liver (to highly water-soluble, inactive metabolites) by the cytochrome P-450 microsomal enzyme system, including CYP3A.

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    Nifedipine has known human metabolites that include Oxidized nifedipine.

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

    5.7 Biological Half-Life

    The terminal elimination half life of nifedipine is approximately 2 hours.

    In patients with normal renal and hepatic function, the plasma half-life of nifedipine is about 2 hours when administered as conventional capsules, and about 7 hours when administered as extended-release tablets (Adalat CC).

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    5.8 Mechanism of Action

    Nifedipine blocks voltage gated L-type calcium channels in vascular smooth muscle and myocardial cells. This blockage prevents the entry of calcium ions into cells during depolarization, reducing peripheral arterial vascular resistance and dilating coronary arteries. These actions reduce blood pressure and increase the supply of oxygen to the heart, alleviating angina.

    The principal physiologic action of nifedipine is to inhibit the transmembrane influx of extracellular calcium ions across the membranes of myocardial cells and vascular smooth muscle cells, without changing serum calcium concentrations. Calcium plays important roles in the excitation-contraction coupling processes of the heart and vascular smooth muscle cells and in the electrical discharge of the specialized conduction cells of the heart. The membranes of these cells contain numerous channels that carry a slow inward current and that are selective for calcium. Activation of these slow calcium channels contributes to the plateau phase (phase 2) of the action potential of cardiac and vascular smooth muscle cells. The exact mechanism whereby nifedipine inhibits calcium ion influx across the slow calcium channels is not known, but the drug is thought to inhibit ion-control gating mechanisms of the channel, deform the slow channel, and/or interfere with release of calcium from the sarcoplasmic reticulum. By inhibiting calcium influx, nifedipine inhibits the contractile processes of cardiac and vascular smooth muscle, thereby dilating the main coronary and systemic arteries.

    American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)

    Nifedipine is a peripheral arterial vasodilator which acts directly on vascular smooth muscle. The binding of nifedipine to voltage-dependent and possibly receptor-operated channels in vascular smooth muscle results in an inhibition of calcium influx through these channels. Stores of intracellular calcium in vascular smooth muscle are limited and thus dependent upon the influx of extracellular calcium for contraction to occur. The reduction in calcium influx by nifedipine causes arterial vasodilation and decreased peripheral vascular resistance which results in reduced arterial blood pressure.

    US Natl Inst Health; DailyMed. Current Medication Information for ADALAT CC (nifedipine) tablet, film coated (June 2009). Available from, as of October 15, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10098

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    06-Jan-2021
    31-Oct-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

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

    API Imports and Exports

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

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - CAPSULE;ORAL - 10MG

    USFDA APPLICATION NUMBER - 18482

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    DOSAGE - CAPSULE;ORAL - 20MG **Federal Regist...DOSAGE - CAPSULE;ORAL - 20MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 18482

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 30MG

    USFDA APPLICATION NUMBER - 19684

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 60MG

    USFDA APPLICATION NUMBER - 19684

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 90MG

    USFDA APPLICATION NUMBER - 19684

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 30MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 30MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20198

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 60MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 60MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20198

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 90MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 90MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20198

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