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    Isradipine

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    RELATED EXCIPIENT COMPANIES

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    2D Structure
    Also known as: 75695-93-1, Dynacirc, Isradipin, Lomir, Isrodipine, Prescal
    Molecular Formula
    C19H21N3O5
    Molecular Weight
    371.4  g/mol
    InChI Key
    HMJIYCCIJYRONP-UHFFFAOYSA-N
    FDA UNII
    YO1UK1S598
    A potent antagonist of CALCIUM CHANNELS that is highly selective for VASCULAR SMOOTH MUSCLE. It is effective in the treatment of chronic stable angina pectoris, hypertension, and congestive cardiac failure.
    Isradipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of isradipine is as a Calcium Channel Antagonist.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-O-methyl 5-O-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
    2.1.2 InChI
    InChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3
    2.1.3 InChI Key
    HMJIYCCIJYRONP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(C(C(=C(N1)C)C(=O)OC(C)C)C2=CC=CC3=NON=C32)C(=O)OC
    2.2 Other Identifiers
    2.2.1 UNII
    YO1UK1S598
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Dynacirc

    2. Isradipine, (+-)-isomer

    3. Isradipine, (r)-isomer

    4. Isradipine, (s)-isomer

    5. Lomir

    6. Pn 200-110

    7. Pn 205 033

    8. Pn 205 034

    9. Pn 205-033

    10. Pn 205-034

    11. Pn 205033

    12. Pn 205034

    13. Pn-200-110

    14. Pn-205-033

    15. Pn-205-034

    16. Pn205033

    17. Pn205034

    2.3.2 Depositor-Supplied Synonyms

    1. 75695-93-1

    2. Dynacirc

    3. Isradipin

    4. Lomir

    5. Isrodipine

    6. Prescal

    7. Esradin

    8. Dynacirc Cr

    9. Clivoten

    10. Pn 200-110

    11. Dynacrine

    12. Isradipinum [latin]

    13. Isradipino [spanish]

    14. Pn-200-110

    15. Rebriden

    16. Dynacire

    17. Dynacire Cr

    18. (+/-)-isradipine

    19. Isradipine (dynacirc)

    20. Pn 200

    21. C19h21n3o5

    22. (+-)-isradipine

    23. 3-isopropyl 5-methyl 4-(benzo[c][1,2,5]oxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    24. 3-o-methyl 5-o-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    25. 3,5-pyridinedicarboxylic Acid, 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-, Methyl 1-methylethyl Ester

    26. Nsc-759892

    27. Yo1uk1s598

    28. 131970-21-3

    29. 3,5-pyridinedicarboxylic Acid, 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-2,6-dimethyl-, Methyl 1-methylethyl Ester

    30. Isradipine D3

    31. Isradipinum

    32. Isradipino

    33. Dsstox_cid_3179

    34. Dsstox_rid_76907

    35. Dsstox_gsid_23179

    36. Icaz

    37. 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinecarboxylic Acid Methyl 1-methylethyl Ester

    38. Smr000466320

    39. Smr002529690

    40. Dynacirc (tn)

    41. Isradipine (usp/inn)

    42. Sr-01000597526

    43. Mfcd00153820

    44. Unii-yo1uk1s598

    45. Isradipine [usan:usp:inn:ban]

    46. Ncgc00016931-01

    47. (-)-isradipine

    48. (plusmn)-isradipine

    49. Cas-75695-93-1

    50. Pn200-110

    51. Isopropyl Methyl (+-)-4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    52. Spectrum_000218

    53. Isradipine [mi]

    54. Pn-200110

    55. Isradipine [inn]

    56. Prestwick0_001021

    57. Prestwick1_001021

    58. Prestwick2_001021

    59. Prestwick3_001021

    60. (.+/-.)-isradipine

    61. Isradipine [usan]

    62. Isradipine [vandf]

    63. Isradipine [mart.]

    64. Chembl1648

    65. Isradipine [usp-rs]

    66. Isradipine [who-dd]

    67. Schembl34555

    68. Bspbio_001201

    69. Kbioss_000698

    70. 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Methyl 1-methylethyl Ester

    71. Mls000759425

    72. Mls001424076

    73. Mls002154106

    74. Mls003915633

    75. Mls006010138

    76. O5-methyl O3-propan-2-yl 4-(2,1,3-benzoxadiazol-7-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    77. Spbio_003062

    78. Bpbio1_001323

    79. Chebi:6073

    80. Chembl315436

    81. Gtpl4488

    82. Chembl3211306

    83. Dtxsid4023179

    84. Isradipine [orange Book]

    85. Kbio2_000698

    86. Kbio2_003266

    87. Kbio2_005834

    88. Isradipine [ep Monograph]

    89. Hms1571m03

    90. Hms2051j12

    91. Hms2098m03

    92. Hms2235o12

    93. Hms3268d21

    94. Hms3393j12

    95. Hms3413a15

    96. Hms3655c17

    97. Hms3677a15

    98. Hms3715m03

    99. Hms3884e06

    100. Isradipine [usp Monograph]

    101. Pharmakon1600-02300234

    102. (non-isotopelabelled)isradipine-d7

    103. Act02697

    104. Bcp06719

    105. Hy-b0233

    106. Benzo[1,2,5]oxadiazol-4-aldehyde

    107. Tox21_110690

    108. Bdbm50436176

    109. Nsc759892

    110. S1662

    111. Akos015895129

    112. Isradipine, >=98% (hplc), Solid

    113. Tox21_110690_1

    114. Ac-8539

    115. Ccg-101027

    116. Ccg-213711

    117. Db00270

    118. Hs-0085

    119. Nc00277

    120. Nsc 759892

    121. Isopropyl Methyl 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    122. Ncgc00025341-01

    123. Ncgc00025341-02

    124. Ncgc00025341-03

    125. Ncgc00025341-06

    126. 3,5-pyridinedicarboxylic Acid, 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-2,6-dimethyl-, Methyl 1-methylethyl Ester (9ci)

    127. 3,5-pyridinedicarboxylic Acid, 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-, Methyl 1-methylethyl Ester, (+-)-

    128. 4-(2,1,3-benzooxadiazol-4-yl)-2.6-dimethyl-1,4-dihydro-3-isopropyloxycarbonylpyridine-5-carboxylic Acid Methyl Ester

    129. 4-(4-benzofurazanyl)-1,-4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Methyl 1-methhylethyl Ester

    130. 4-(4-benzofurazanyl)-1,4-dihydro-2,-6-dimethyl-3,5-pyridinedicarboxylic Acid Methyl 1-methylethyl Ester

    131. Isopropyl 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-3-pyridinecarboxylate

    132. Methyl 1-methylethyl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    133. Db-055981

    134. Ab00514007

    135. Ft-0627542

    136. I0876

    137. Sw220017-1

    138. D00349

    139. Ab00514007_02

    140. Ab00514007_03

    141. 695i931

    142. Q414873

    143. J-513454

    144. Sr-01000597526-1

    145. Sr-01000597526-2

    146. Sr-01000597526-8

    147. Brd-a90799790-001-03-3

    148. Brd-a90799790-001-10-8

    149. Isradipine, European Pharmacopoeia (ep) Reference Standard

    150. Isradipine, United States Pharmacopeia (usp) Reference Standard

    151. Isopropyl Methyl 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-2,6-dimet

    152. 3,5-pyridinedicarboxylic Acid, 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-, Methyl 1-methylethyl Ester, (+/-)-

    153. 3,5-pyridinedicarboxylic Acid, 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-, Methyl 1-methylethyl Ester, (.+/-.)-

    154. 3-isopropyl 5-methyl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate #

    155. 3-methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    156. 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Isopropyl Methyl Ester

    157. Isopropyl Methyl (+/-)-4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    158. Isopropyl Methyl (.+/-.)-4-(4-benzfurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    159. Isopropyl Methyl (.+/-.)-4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 371.4 g/mol
    Molecular Formula C19H21N3O5
    XLogP34.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count6
    Exact Mass371.14812078 g/mol
    Monoisotopic Mass371.14812078 g/mol
    Topological Polar Surface Area104 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity685
    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 2  
    Drug NameIsradipine
    PubMed HealthIsradipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
    Drug LabelIsradipine is a calcium antagonist available for oral administration in capsules containing 2.5 mg or 5 mg. The structural formula of isradipine is:Chemically, isradipine is 3,5-Pyridinedicarboxylic acid, 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl...
    Active IngredientIsradipine
    Dosage FormCapsule
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyWatson Labs; Mikah Pharma

    2 of 2  
    Drug NameIsradipine
    PubMed HealthIsradipine (By mouth)
    Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
    Drug LabelIsradipine is a calcium antagonist available for oral administration in capsules containing 2.5 mg or 5 mg. The structural formula of isradipine is:Chemically, isradipine is 3,5-Pyridinedicarboxylic acid, 4-(4-benzofurazanyl)-1,4-dihydro-2,6-dimethyl...
    Active IngredientIsradipine
    Dosage FormCapsule
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyWatson Labs; Mikah Pharma

    4.2 Drug Indication

    For the management of mild to moderate essential hypertension. It may be used alone or concurrently with thiazide-type diuretics.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Isradipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through L-type calcium channels. 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 isradipine result in an overall decrease in blood pressure.

    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.)

    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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ISRADIPINE
    5.3.2 FDA UNII
    YO1UK1S598
    5.3.3 Pharmacological Classes
    Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]
    5.4 ATC Code

    C - Cardiovascular system

    C08 - Calcium channel blockers

    C08C - Selective calcium channel blockers with mainly vascular effects

    C08CA - Dihydropyridine derivatives

    C08CA03 - Isradipine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Isradipine is 90%-95% absorbed and is subject to extensive first-pass metabolism, resulting in a bioavailability of about 15%-24%.

    Route of Elimination

    Approximately 60% to 65% of an administered dose is excreted in the urine and 25% to 30% in the feces.

    5.6 Metabolism/Metabolites

    Hepatic. Completely metabolized prior to excretion and no unchanged drug is detected in the urine.

    5.7 Biological Half-Life

    8 hours

    5.8 Mechanism of Action

    Isradipine 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. CCBs target L-type calcium channels, the major channel in muscle cells that mediates contraction. Similar to other DHP CCBs, isradipine 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 isradipine additional arterial selectivity. At therapeutic sub-toxic concentrations, isradipine has little effect on cardiac myocytes and conduction cells.