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    Chemistry

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    Also known as: 72509-76-3, Plendil, Flodil, Renedil, Feloday, Munobal
    Molecular Formula
    C18H19Cl2NO4
    Molecular Weight
    384.2  g/mol
    InChI Key
    RZTAMFZIAATZDJ-UHFFFAOYSA-N
    FDA UNII
    OL961R6O2C
    Felodipine
    A dihydropyridine calcium antagonist with positive inotropic effects. It lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels.
    Felodipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of felodipine is as a Calcium Channel Antagonist.
    1 2D Structure

    Felodipine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-O-ethyl 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
    2.1.2 InChI
    InChI=1S/C18H19Cl2NO4/c1-5-25-18(23)14-10(3)21-9(2)13(17(22)24-4)15(14)11-7-6-8-12(19)16(11)20/h6-8,15,21H,5H2,1-4H3
    2.1.3 InChI Key
    RZTAMFZIAATZDJ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)C1=C(NC(=C(C1C2=C(C(=CC=C2)Cl)Cl)C(=O)OC)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    OL961R6O2C
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Agon

    2. Felo Biochemie

    3. Felo Puren

    4. Felo-puren

    5. Felobeta

    6. Felocor

    7. Felodipin 1a Pharma

    8. Felodipin Abz

    9. Felodipin Al

    10. Felodipin Azu

    11. Felodipin Dura

    12. Felodipin Heumann

    13. Felodipin Ratiopharm

    14. Felodipin Stada

    15. Felodipin Von Ct

    16. Felodipin-ratiopharm

    17. Felodur

    18. Felogamma

    19. Fensel

    20. Flodil

    21. H 154 82

    22. H 154-82

    23. H 15482

    24. Heumann, Felodipin

    25. Modip

    26. Munobal

    27. Perfudal

    28. Plendil

    29. Renedil

    30. Von Ct, Felodipin

    2.3.2 Depositor-Supplied Synonyms

    1. 72509-76-3

    2. Plendil

    3. Flodil

    4. Renedil

    5. Feloday

    6. Munobal

    7. Splendil

    8. Dl-felodipine

    9. Perfudal

    10. Prevex

    11. Hydac

    12. Modip

    13. Agon

    14. Felodipina

    15. Felodipinum

    16. Felodipinum [inn-latin]

    17. 3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    18. Felodipina [inn-spanish]

    19. H 154/82

    20. Felodipine (plendil)

    21. C08ca02

    22. Cgh-869

    23. Plendil Er

    24. 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Ethyl Methyl Ester

    25. 5-o-ethyl 3-o-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    26. Felogard

    27. Mfcd00868316

    28. Penedil

    29. Preslow

    30. Munobal Retard

    31. Nsc-760343

    32. Plendil Retard

    33. H-154/82

    34. Plendil Depottab

    35. (+-)-ethyl Methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    36. Mls000069629

    37. Ol961r6o2c

    38. Chebi:585948

    39. Felodur Er

    40. Agon Sr

    41. 3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

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

    43. Ncgc00015455-03

    44. Plandil

    45. Smr000058204

    46. C18h19cl2no4

    47. Dsstox_cid_3042

    48. Dsstox_rid_76848

    49. Dsstox_gsid_23042

    50. Felodipine [usan:ban:inn]

    51. Logimax

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

    53. (+/-)-ethyl Methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    54. (rs)-3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    55. Plendil (tn)

    56. Sr-01000075890

    57. Brn 4331472

    58. Unii-ol961r6o2c

    59. Perfuda

    60. Plendil;renedil

    61. Felodipine, Solid

    62. Felodipine,(s)

    63. Felodipine [usan:usp:inn:ban]

    64. 3,5-dicarboxylate

    65. Felodipine- Bio-x

    66. Prestwick_797

    67. Cas-72509-76-3

    68. 3,5-pyridinedicarboxylic Acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, Ethyl Methyl Ester

    69. Felodipine (dl Form)

    70. Felodipine [mi]

    71. Felodipine [inn]

    72. Felodipine [jan]

    73. Opera_id_1873

    74. Prestwick0_000478

    75. Prestwick1_000478

    76. Prestwick2_000478

    77. Prestwick3_000478

    78. (.+/-.)-felodipine

    79. Felodipine [usan]

    80. Felodipine [vandf]

    81. F 9677

    82. Felodipine [mart.]

    83. 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinecarboxylic Acid Ethyl Methyl Ester

    84. Chembl1480

    85. Felodipine [usp-rs]

    86. Felodipine [who-dd]

    87. Lopac0_000508

    88. Schembl26398

    89. Bspbio_000616

    90. Ae-641/11429675

    91. Mls001077361

    92. Mls001333735

    93. Mls002153409

    94. Mls002153832

    95. Mls003876820

    96. Bidd:gt0733

    97. Spbio_002555

    98. Bpbio1_000678

    99. Felodipine (jp17/usp/inn)

    100. Gtpl4190

    101. (r)-(+)-felodipine-[d5]

    102. Chembl3196476

    103. Dtxsid4023042

    104. Felodipine [orange Book]

    105. Schembl13460298

    106. Felodipine [ep Monograph]

    107. Felodipine [usp Impurity]

    108. Lexxel Component Felodipine

    109. Bdbm189379

    110. Felodipine [usp Monograph]

    111. Hms1569o18

    112. Hms2089j05

    113. Hms2096o18

    114. Hms2232d24

    115. Hms3259f12

    116. Hms3261f17

    117. Hms3651o21

    118. Hms3713o18

    119. Hms3884i14

    120. Pharmakon1600-01505887

    121. Bcp02192

    122. Bcp22685

    123. Hy-b0309

    124. 2,6-dimethyl-1,4-dihydropyridine-

    125. Tox21_110155

    126. Tox21_500508

    127. Ca-236

    128. Nsc760343

    129. S1885

    130. Felodipine Component Of Lexxel

    131. Akos015891545

    132. Felodipine 100 Microg/ml In Methanol

    133. Tox21_110155_1

    134. Ac-2124

    135. Bcp9000680

    136. Ccg-204599

    137. Db01023

    138. Ks-1264

    139. Lp00508

    140. Nc00721

    141. Nsc 760343

    142. Sdccgsbi-0050492.p002

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

    144. Ncgc00015455-04

    145. Ncgc00015455-05

    146. Ncgc00015455-06

    147. Ncgc00015455-07

    148. Ncgc00015455-08

    149. Ncgc00015455-10

    150. Ncgc00015455-24

    151. Ncgc00024087-02

    152. Ncgc00093906-01

    153. Ncgc00093906-02

    154. Ncgc00261193-01

    155. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-4-(2,3-dichlorophenyl)-2,6-dimethyl-, Ethyl Methyl Ester

    156. 3,5-pyridinedicarboxylic Acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, Ethyl Methyl Ester, (+-)-

    157. 4-(2,3-dichloro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic Acid 3-ethyl Ester 5-methyl Ester

    158. Ac-24403

    159. Bf164445

    160. Felodipine 100 Microg/ml In Acetonitrile

    161. Smr002529504

    162. Sy053174

    163. 3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-

    164. Eu-0100508

    165. F0814

    166. Ft-0626393

    167. Ft-0660933

    168. Ft-0668475

    169. Sw219299-1

    170. En300-70726

    171. D00319

    172. 509f763

    173. Q420644

    174. Sr-01000075890-1

    175. Sr-01000075890-4

    176. Brd-a30815329-001-03-0

    177. Z239864852

    178. Felodipine, European Pharmacopoeia (ep) Reference Standard

    179. Felodipine, United States Pharmacopeia (usp) Reference Standard

    180. 3-ethyl5-methyl4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    181. (.+/-.) Ethyl Methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    182. 3,5-pyridinedicarboxylic Acid 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, Ethyl Methyl Ester, (+/-)-

    183. 3,5-pyridinedicarboxylic Acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-ethyl-5-methylester

    184. 3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate #

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 384.2 g/mol
    Molecular Formula C18H19Cl2NO4
    XLogP33.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count6
    Exact Mass383.0691135 g/mol
    Monoisotopic Mass383.0691135 g/mol
    Topological Polar Surface Area64.6 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity614
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameFelodipine
    PubMed HealthFelodipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
    Drug LabelFelodipine is a calcium antagonist (calcium channel blocker). Felodipine is a dihydropyridine derivative that is chemically described as ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2, 6-dimethyl-3,5-pyridinedicarboxylate. Its molecular formula...
    Active IngredientFelodipine
    Dosage FormTablet, extended release
    RouteOral
    Strength2.5mg; 5mg; 10mg
    Market StatusPrescription
    CompanyVintage Pharms; Wockhardt; Glenmark Generics; Mutual Pharm; Aurobindo Pharma; Torrent Pharms; Ranbaxy Labs; Mylan; Heritage Pharms

    2 of 4  
    Drug NamePlendil
    PubMed HealthFelodipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
    Drug LabelPLENDIL (felodipine) is a calcium antagonist (calcium channel blocker). Felodipine is a dihydropyridine derivative that is chemically described as ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate. Its empirica...
    Active IngredientFelodipine
    Dosage FormTablet, extended release
    RouteOral
    Strength2.5mg; 5mg; 10mg
    Market StatusPrescription
    CompanyAstrazeneca

    3 of 4  
    Drug NameFelodipine
    PubMed HealthFelodipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
    Drug LabelFelodipine is a calcium antagonist (calcium channel blocker). Felodipine is a dihydropyridine derivative that is chemically described as ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2, 6-dimethyl-3,5-pyridinedicarboxylate. Its molecular formula...
    Active IngredientFelodipine
    Dosage FormTablet, extended release
    RouteOral
    Strength2.5mg; 5mg; 10mg
    Market StatusPrescription
    CompanyVintage Pharms; Wockhardt; Glenmark Generics; Mutual Pharm; Aurobindo Pharma; Torrent Pharms; Ranbaxy Labs; Mylan; Heritage Pharms

    4 of 4  
    Drug NamePlendil
    PubMed HealthFelodipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
    Drug LabelPLENDIL (felodipine) is a calcium antagonist (calcium channel blocker). Felodipine is a dihydropyridine derivative that is chemically described as ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate. Its empirica...
    Active IngredientFelodipine
    Dosage FormTablet, extended release
    RouteOral
    Strength2.5mg; 5mg; 10mg
    Market StatusPrescription
    CompanyAstrazeneca

    4.2 Drug Indication

    For the treatment of mild to moderate essential hypertension.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Felodipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. There are at least five different types of calcium channels in Homo sapiens: L-, N-, P/Q-, R- and T-type. It was widely accepted that CCBs target L-type calcium channels, the major channel in muscle cells that mediates contraction; however, some studies have shown that felodipine also binds to and inhibits T-type calcium channels. T-type calcium channels are most commonly found on neurons, cells with pacemaker activity and on osteocytes. The pharmacologic significance of T-type calcium channel blockade is unknown. Felodipine also binds to calmodulin and inhibits calmodulin-dependent calcium release from the sarcoplasmic reticulum. The effect of this interaction appears to be minor. Another study demonstrated that felodipine attenuates the activity of calmodulin-dependent cyclic nucleotide phosphodiesterase (CaMPDE) by binding to the PDE-1B1 and PDE-1A2 enzyme subunits. CaMPDE is one of the key enzymes involved in cyclic nucleotides and calcium second messenger systems. Felodipine also acts as an antagonist to the mineralcorticoid receptor by competing with aldosterone for binding and blocking aldosterone-induced coactivator recruitment of the mineralcorticoid receptor. Felodipine is able to bind to skeletal and cardiac muscle isoforms of troponin C, one of the key regulatory proteins in muscle contraction. Though felodipine exhibits binding to many endogenous molecules, its vasodilatory effects are still thought to be brought about primarily through inhibition of voltage-gated L-type calcium channels. Similar to other DHP CCBs, felodipine binds directly to inactive calcium channels stabilizing their inactive conformation. Since arterial smooth muscle depolarizations are longer in duration than cardiac muscle depolarizations, inactive channels are more prevalent in smooth muscle cells. Alternative splicing of the alpha-1 subunit of the channel gives felodipine additional arterial selectivity. At therapeutic sub-toxic concentrations, felodipine has little effect on cardiac myocytes and conduction cells.

    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.)

    Anti-Arrhythmia Agents

    Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    FELODIPINE
    5.3.2 FDA UNII
    OL961R6O2C
    5.3.3 Pharmacological Classes
    Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]
    5.4 ATC Code

    C08CA02

    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

    C08CA02 - Felodipine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Is completely absorbed from the gastrointestinal tract; however, extensive first-pass metabolism through the portal circulation results in a low systemic availability of 15%. Bioavailability is unaffected by food.

    Route of Elimination

    Although higher concentrations of the metabolites are present in the plasma due to decreased urinary excretion, these are inactive. Animal studies have demonstrated that felodipine crosses the blood-brain barrier and the placenta.

    Volume of Distribution

    10 L/kg

    Clearance

    0.8 L/min [Young healthy subjects]

    5.6 Metabolism/Metabolites

    Hepatic metabolism primarily via cytochrome P450 3A4. Six metabolites with no appreciable vasodilatory effects have been identified.

    5.7 Biological Half-Life

    17.5-31.5 hours in hypertensive patients; 19.1-35.9 hours in elderly hypertensive patients; 8.5-19.7 in healthy volunteers.

    5.8 Mechanism of Action

    Felodipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through voltage-gated L-type calcium channels. It reversibly competes against nitrendipine and other DHP CCBs for DHP binding sites in vascular smooth muscle and cultured rabbit atrial cells. Calcium ions entering the cell through these channels bind to calmodulin. Calcium-bound calmodulin then binds to and activates myosin light chain kinase (MLCK). Activated MLCK catalyzes the phosphorylation of the regulatory light chain subunit of myosin, a key step in muscle contraction. Signal amplification is achieved by calcium-induced calcium release from the sarcoplasmic reticulum through ryanodine receptors. Inhibition of the initial influx of calcium decreases the contractile activity of arterial smooth muscle cells and results in vasodilation. The vasodilatory effects of felodipine result in an overall decrease in blood pressure. Felodipine may be used to treat mild to moderate essential hypertension.

    API Reference Price

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    07-Apr-2021
    02-Sep-2024
    KGS
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    Average Price (USD/KGS)

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    Total Quantity (KGS)

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

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    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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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**

    USFDA APPLICATION NUMBER - 19834

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 2.5M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 2.5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 19834

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 5MG ...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 19834

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