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    Alfacalcidol

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

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    REF. STANDARDS & IMPURITIES

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    2D Structure
    Also known as: 1-hydroxycholecalciferol, Alphacalcidol, 41294-56-8, 1alpha-hydroxyvitamin d3, Alfarol, Bondiol
    Molecular Formula
    C27H44O2
    Molecular Weight
    400.6  g/mol
    InChI Key
    OFHCOWSQAMBJIW-AVJTYSNKSA-N
    FDA UNII
    URQ2517572
    Alfacalcidol, or 1-alpha-hydroxycholecalciferol or 1-alpha-hydroxyvitamin D3, is a non-endogenous analogue of [vitamin D]. It plays an essential function in calcium homeostasis and bone metabolism. Alfacaldisol is activated by the enzyme 25-hydroxylase in the liver to mediate its effects in the body, or most importantly, the kidneys and bones. The pharmacological actions of alfacalcidol are prolonged than vitamin D because a negative feedback mechanism regulates the final activation step of vitamin D in the kidneys. Alfacalcidol is available in oral and intravenous formulations. In Canada, it is marketed as ONE-ALPHA, which manages hypocalcemia, secondary hyperparathyroidism, and osteodystrophy in adults with chronic renal failure. In approving European countries, alfacalcidol is also indicated for managing nutritional and malabsorptive rickets and osteomalacia, vitamin D-dependent rickets and osteomalacia, and hypophosphataemic vitamin D resistant rickets and osteomalacia.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
    2.1.2 InChI
    InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1
    2.1.3 InChI Key
    OFHCOWSQAMBJIW-AVJTYSNKSA-N
    2.1.4 Canonical SMILES
    CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
    2.1.5 Isomeric SMILES
    C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    URQ2517572
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1 Alpha-hydroxycholecalciferol

    2. 1 Alpha-hydroxyvitamin D3

    3. 1-alpha-oxycholecalciferol

    4. 1-hydroxycholecalciferol

    5. 1-hydroxycholecalciferol, (1alpha,3alpha-(5z,7e))-isomer

    6. 1-hydroxycholecalciferol, (1beta)-(5z)-isomer

    7. 1-hydroxycholecalciferol, (1beta,3beta-(5e,7e))-isomer

    8. 1-hydroxycholecalciferol, Aluminum Salt

    9. 1alpha-ohd3

    10. Alfad

    11. Alphacalcidol

    12. Bondiol

    13. Eenalfadrie

    14. Einsalpha

    15. Etalpha

    16. Oksidevit

    17. One-alpha

    18. Un-alfa

    2.3.2 Depositor-Supplied Synonyms

    1. 1-hydroxycholecalciferol

    2. Alphacalcidol

    3. 41294-56-8

    4. 1alpha-hydroxyvitamin D3

    5. Alfarol

    6. Bondiol

    7. Einsalpha

    8. Etalpha

    9. Oxydevit

    10. 1-hydroxyvitamin D3

    11. 1alpha-hydroxycholecalciferol

    12. Alsiodol

    13. Alpha-calcidol

    14. One-alpha

    15. Alfacalcidolum

    16. Un-alpha

    17. 1alpha-hydroxy-vitamin D3

    18. Vitamin D3, 1alpha-hydroxy-

    19. Alpharol

    20. Tevabone

    21. Un Alpha

    22. Un Alfa

    23. .alpha.-calcidol

    24. 1.alpha.-hydroxyvitamin D3

    25. 1-alpha-vitamin D

    26. 1.alpha.(oh)d3

    27. 1-alpha-hydroxy-vitamin D3

    28. 1.alpha-hydroxycholecalciferol

    29. 1.alpha.-hydroxycholecalciferol

    30. (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

    31. Chebi:31186

    32. (5z,7e)-9,10-seco-5,7,10(19)-cholestatrien-1alpha,3beta-diol

    33. Alpha D3

    34. 1

    35. A-hydroxy-5,6-trans-vitamin D3

    36. Urq2517572

    37. (1r,3s)-5-[2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

    38. 1alpha-hydroxyvitamin D3 / 1alpha-hydroxycholecalciferol

    39. 1alpha-oh-d3

    40. 9,10-secocholesta-5,7,10(19)-triene-1alpha,3beta-diol

    41. Sinovul

    42. (5z,7e)-(1s,3r)-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol

    43. Alpha-d3

    44. Alpha D 3

    45. 1 Alpha-hydroxyvitamin D3

    46. Alfacalcidolum [inn-latin]

    47. Alfacalcidiol

    48. Onealfa

    49. Diseon

    50. 1-alpha-hydroxycholecalciferol

    51. Alfacalcidol [inn:ban:jan]

    52. Ccris 3341

    53. Unii-urq2517572

    54. Alsiodol (tn)

    55. Einecs 255-297-1

    56. Eb 644

    57. 1a-hydroxycholecalciferol, Alfacalcidol

    58. 1-hydroxy Vitamin D3

    59. 1-alpha-hydroxyvitamin D

    60. Alfacalcidol (jan/inn)

    61. Udpgatriammoniumsalt

    62. Alfacalcidol [inn]

    63. Alfacalcidol [jan]

    64. 1-alpha-hydroxyvitamin D3

    65. Schembl3063

    66. Alfacalcidol [mart.]

    67. Alfacalcidol [who-dd]

    68. Chembl1601669

    69. Dtxsid0022569

    70. Chebi:94779

    71. Alfacalcidol [ep Monograph]

    72. 1(alpha)-hydroxyvitamin D3

    73. Cs-m0939

    74. Ex-a4432

    75. Lmst03020231

    76. Zinc12484965

    77. Akos017343040

    78. Cs-0389

    79. Db01436

    80. Lp-0030

    81. 9,10-secocholesta-5,7,10(19)-triene-1,3-diol, (1.alpha.,3.beta.,5z,7e)-

    82. Hy-10003

    83. Alfacalcidol 100 Microg/ml In Acetonitrile

    84. 1.alpha.-hydroxycholecalciferol [mi]

    85. 1alpha-hydroxyvitamin D3, >=97.0% (hplc)

    86. D01518

    87. Q155883

    88. Q-200608

    89. 9,10-secocholesta-,7,10(19)-triene-1alpha,3beta-diol

    90. (1s,3r,5z,7e)-9,10-secocholesta-5,7,10-triene-1,3-diol

    91. Alfacalcidol, European Pharmacopoeia (ep) Reference Standard

    92. (1alpha,3beta,5z,7e)-secocholesta-5,7,10(19)-triene-1,3-diol

    93. (5z,7e)-9,10-secocholesta-5,7,10(19)-triene-1alpha,3beta-diol

    94. (1?,3?,5z,7e)-9,10-secocholesta-5,7,10(19)-triene-1,3-diol

    95. 9,10-secocholesta-5,7,10(19)-triene-1,3-diol, (1alpha,3beta,5z,7e)-

    96. (1alpha,3beta,5z,7e)-9,10-secocholesta-5,7,10(19)-triene-1,3-diol

    97. (5z,7e)-9,10-secocholesta-5,7,10(19)-triene-1.alpha.,3.beta.-diol

    98. 9,10-secocholesta-5,7,10(19)-triene-1,3-diol, (1-alpha,3-beta,5z,7e)-

    99. Alfacalcidol For System Suitability, European Pharmacopoeia (ep) Reference Standard

    100. (1r,3s,z)-5-((e)-2-((1r,3as,7ar)-7a-methyl-1-((r)-6-methylheptan-2-yl)hexahydro-1h-inden-4(2h)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol

    101. 1,3-cyclohexanediol, 5-((2e)-2-((1r,3as,7ar)-1-((1r)-1,5-dimethylhexyl)octahydro-7a-methyl-4h-inden-4-ylidene)ethylidene)-4-methylene-, (1r,3r)-

    102. M9b

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 400.6 g/mol
    Molecular Formula C27H44O2
    XLogP36.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count6
    Exact Mass400.334130642 g/mol
    Monoisotopic Mass400.334130642 g/mol
    Topological Polar Surface Area40.5 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity643
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Alfacalcidol is indicated in adult patients with chronic renal failure for the management of hypocalcemia, secondary hyperparathyroidism, or osteodystrophy. Alfacalcidol is indicated in the management of nutritional and malabsorptive rickets and osteomalacia, vitamin D-dependent rickets and osteomalacia, and hypophosphataemic vitamin D resistant rickets and osteomalacia.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Alfacalcidol works to increase serum levels of calcium by stimulating intestinal calcium absorption, reabsorption of calcium from bone, and possibly the renal reabsorption of calcium. It also modestly promotes intestinal phosphorus absorption. In patients with renal failure, alfacalcidol increased intestinal calcium and phosphorus absorption in a dose-related manner. This increase in calcium and phosphorus levels occurs within three days following drug administration: this effect was reversed within three days of drug discontinuation. In patients with chronic renal failure, serum calcium levels were elevated while parathyroid hormone and alkaline phosphatase levels returned to normal levels within five days following alfacalcidol administration. Since alfacalcidol suppresses parathyroid hormone, a reduction in parathyroid hormone levels is achieved more rapidly in patients on intermittent intravenous therapy, with significant reductions occurring within three months of therapy. In patients receiving daily oral therapy of alfacalcidol, the time it takes alfacalcidol to normalize plasma calcium levels may be up to several months, possibly reflecting calcium being utilized for bone mineralization. In patients with nutritional osteomalacia, alfacalcidol increased calcium absorption with six hours of oral administration and the effects peaked at 24 hours.

    5.2 MeSH Pharmacological Classification

    Bone Density Conservation Agents

    Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)

    5.3 ATC Code

    A - Alimentary tract and metabolism

    A11 - Vitamins

    A11C - Vitamin a and d, incl. combinations of the two

    A11CC - Vitamin d and analogues

    A11CC03 - Alfacalcidol

    5.4 Absorption, Distribution and Excretion

    Absorption

    Alfacalcidol is absorbed passively and almost completely in the small intestine.

    5.5 Metabolism/Metabolites

    Alfacalcidol is rapidly converted in the liver to 1,25-dihydroxyvitamin D, which is essentially the metabolite of vitamin D that regulates calcium and phosphate metabolism. Alfacalcidol is further metabolized to other polar inactive metabolites, excreted primarily through the bile.

    5.6 Biological Half-Life

    The half-life of alfacalcidol ranges from three to four hours.

    5.7 Mechanism of Action

    In conditions like chronic renal failure, renal bone disease, hypoparathyroidism, and vitamin D dependent rickets, the kidneys' capacity for 1-hydroxylation is impaired, leading to reduced production of endogenous 1,25-dihydroxyvitamin D and aberrated mineral metabolism. As an active and potent analog of vitamin D, alfacalcidol works to restore the functions and activities of endogenous 1,25-dihydroxyvitamin D.