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    Lacidipine

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

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    2D Structure
    Also known as: 103890-78-4, Lacipil, Motens, Gr-43659x, Trans lacidipine, Gr 43659x
    Molecular Formula
    C26H33NO6
    Molecular Weight
    455.5  g/mol
    InChI Key
    GKQPCPXONLDCMU-CCEZHUSRSA-N
    FDA UNII
    260080034N
    Lacidipine is a lipophilic dihydropyridine calcium antagonist with an intrinsically slow onset of activity. Due to its long duration of action, lacidipine does not lead to reflex tachycardia. It displays specificity in the vascular smooth muscle, where it acts as an antihypertensive agent to dilate peripheral arterioles and reduce blood pressure. Compared to other dihydropyridine calcium antagonists, lacidipine exhibits a greater antioxidant activity which may confer potentially beneficial antiatherosclerotic effects. Lacidipine is a highly lipophilic molecule that interacts with the biological membranes. Through radiotracer analysis, it was determined that lacidipine displays a high membrane partition coefficient leading to accumulation of the drug in the membrane and slow rate of membrane washout. When visualized by small-angle X-ray diffraction with angstrom resolution to examine its location within the membranes, lacidipine was found deep within the membrane's hydrocarbon core. These results may explain the long clinical half-life of lacidipine. In randomised, well-controlled trials, administration of daily single-dose lacidipine ranging from 2-6 mg demonstrated comparable antihypertensive efficacy similar to that of other long-acting dihydropyridine calcium antagonists, thiazide diuretics, atenolol (a beta-blocker) and enalapril (an ACE inhibitor). It is available as once-daily oral tablets containing 2 or 4 mg of the active compound commonly marketed as Lacipil or Motens. It is not currently FDA-approved.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    diethyl 2,6-dimethyl-4-[2-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
    2.1.2 InChI
    InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14+
    2.1.3 InChI Key
    GKQPCPXONLDCMU-CCEZHUSRSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2C=CC(=O)OC(C)(C)C)C(=O)OCC)C)C
    2.1.5 Isomeric SMILES
    CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2/C=C/C(=O)OC(C)(C)C)C(=O)OCC)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    260080034N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Caldine

    2. Gr 43659x

    3. Gr-43659x

    4. Lacimen

    5. Lacipil

    6. Motens

    2.3.2 Depositor-Supplied Synonyms

    1. 103890-78-4

    2. Lacipil

    3. Motens

    4. Gr-43659x

    5. Trans Lacidipine

    6. Gr 43659x

    7. Lacidipine (lacipil, Motens)

    8. Diethyl 2,6-dimethyl-4-[2-[(e)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

    9. Gx-1048

    10. Sn-305

    11. 4-(o-((e)-2-carboxyvinyl)phenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid, 4-tert-butyl Diethyl Ester

    12. Lacimen

    13. Dsstox_cid_26429

    14. Dsstox_rid_81607

    15. Dsstox_gsid_46429

    16. 3,5-pyridinedicarboxylic Acid, 4-(2-(3-(1,1-dimethylethoxy)-3-oxo-1-propenyl)phenyl)-1,4-dihydro-2,6-dimethyl-, Diethyl Ester, (e)-

    17. Diethyl (e)-4-(2-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    18. 260080034n

    19. Lacidipinum [latin]

    20. Lacidipino [spanish]

    21. Lacidipino

    22. Lacidipinum

    23. Lacirex

    24. (e)-diethyl 4-(2-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    25. Smr000466342

    26. Cas-103890-78-4

    27. Sr-05000001445

    28. Gr 43659 X

    29. Viapres

    30. Molap

    31. Lacidipine [usan:inn:ban]

    32. Lacidipine,(s)

    33. Ncgc00164545-01

    34. (e)-diethyl 4-(2-(3-tert-butoxy-3-oxoprop-1-enyl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    35. Lacidipine- Bio-x

    36. Motens (tn)

    37. Unii-260080034n

    38. Lacidipine [mi]

    39. Lacidipine [inn]

    40. Lacidipine [jan]

    41. Lacidipine (usan/inn)

    42. Lacidipine [usan]

    43. Lacidipine [vandf]

    44. Lacidipine [mart.]

    45. Lacidipine [who-dd]

    46. Lacipil, Motens, Lacidipine

    47. Schembl49277

    48. Schembl49278

    49. Mls000759454

    50. Mls001424282

    51. Chembl460291

    52. Chembl1728809

    53. Dtxsid1046429

    54. Schembl13287288

    55. Chebi:94480

    56. Gtpl11740

    57. Chebi:135737

    58. Hms2052f03

    59. Hms2089k22

    60. Hms3713d20

    61. Hms3884i18

    62. (non-isotopelabelled)lacidipine-d9

    63. Bcp02933

    64. Gr43659x

    65. Hy-b0347

    66. Tox21_112174

    67. Gx1048

    68. S1994

    69. Stl454986

    70. Akos005066844

    71. Tox21_112174_1

    72. Zinc100015470

    73. Bcp9000831

    74. Ccg-101153

    75. Ccg-220579

    76. Db09236

    77. Gx 1048

    78. Hs-0086

    79. Nc00403

    80. Ncgc00263529-01

    81. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(2-(3-(1,1-dimethylethoxy)-3-oxo-1-propenyl)phenyl)-, Diethyl Ester, (e)-

    82. Ac-11008

    83. Ac-33195

    84. Bl164603

    85. Cpd000466342

    86. Bcp0726000285

    87. L0276

    88. Sw219840-1

    89. C71162

    90. D04657

    91. Ab00698350-05

    92. Ab01275445-01

    93. Ab01275445_02

    94. Gx-1048,gr-43659x,sn-305

    95. 890l784

    96. A800840

    97. J-001058

    98. Q1163827

    99. Sr-05000001445-1

    100. Sr-05000001445-2

    101. Brd-k05851096-001-01-9

    102. 2,6-dimethyl-4-[2-[(e)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylic Acid Diethyl Ester

    103. Diethyl 2,6-dimethyl-4-[2-[(e)-3-[(2-methylpropan-2-yl)oxy]-3-oxidanylidene-prop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

    104. Diethyl 4-{2-[(1e)-3-tert-butoxy-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

    2.4 Create Date
    2005-09-13
    3 Chemical and Physical Properties
    Molecular Weight 455.5 g/mol
    Molecular Formula C26H33NO6
    XLogP34.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count11
    Exact Mass455.23078777 g/mol
    Monoisotopic Mass455.23078777 g/mol
    Topological Polar Surface Area90.9 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity805
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated for the treatment of hypertension either alone or in combination with other antihypertensive agents, including -adrenoceptor antagonists, diuretics, and ACE-inhibitors.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    acidipine is a specific and potent calcium antagonist with a predominant selectivity for calcium channels in the vascular smooth muscle. Its main action is to dilate predominantly peripheral and coronary arteries, reducing peripheral vascular resistance and lowering blood pressure. Following the oral administration of 4 mg lacidipine to volunteer subjects, a minimal prolongation of QTc interval has been observed (mean QTcF increase between 3.44 and 9.60 ms in young and elderly volunteers).

    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.)

    5.3 ATC Code

    C - Cardiovascular system

    C08 - Calcium channel blockers

    C08C - Selective calcium channel blockers with mainly vascular effects

    C08CA - Dihydropyridine derivatives

    C08CA09 - Lacidipine

    5.4 Absorption, Distribution and Excretion

    Absorption

    Since it is a highly lipophilic compound, lacidpine is rapidly absorbed from the gastrointestinal tract following oral administration with the peak plasma concentrations reached between 30 and 150 minutes of dosing. The peak plasma concentrations display large interindividual variability, with the values ranging from 1.6 to 5.7 g/L following single-dose oral administration of lacidipine 4mg in healthy young volunteers. Absolute bioavailability is less than 10% due to extensive first-pass metabolism in the liver.

    Route of Elimination

    Approximately 70% of the administered dose is eliminated as metabolites in the faeces and the remainder as metabolites in the urine.

    5.5 Metabolism/Metabolites

    Lacidipine undergoes complete CYP3A4-mediated hepatic metabolism, with no parent drug detected in the urine or faeces. The 2 main metabolites have no pharmacological activity.

    5.6 Biological Half-Life

    The average terminal half-life of lacidipine ranges from between 13 and 19 hours at steady state.

    5.7 Mechanism of Action

    By blocking the voltage-dependent L-type calcium channels, it prevents the transmembrane calcium influx. Normally, calcium ions serve as intracellular messengers or activators in exictable cells including vascular smooth muscles. The influx of calcium ultimately causes the excitation and depolarization of the tissues. Lacidipine inhibits the contractile function in the vascular smooth muscle and reduce blood pressure. Due to its high membrane partition coefficient, some studies suggest that lacidipine may reach the receptor via a two-step process; it first binds and accumulates in the membrane lipid bilayer and then diffuses within the membrane to the calcium channel receptor. It is proposed that lacidipine preferentially blocks the inactivated state of the calcium channel. Through its antioxidant properties shared amongst other dihydropyridine calcium channel blockers, lacidipine demonstrates an additional clinical benefit. Its antiatherosclerotic effects are mediated by suppressing the formation of reactive oxygen species (ROS) and subsequent inflammatory actions by chemokines, cytokines and adhesion molecules, thus reducing atherosclerotic lesion formation. Lacidipine may also suppress cell proliferation and migration in smooth muscle cells and suppress the expression of matrix metalloproteinases, which affects the stability of atheromatous plaques.