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Calcifediol

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Chemistry

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Also known as: Calcidiol, 25-hydroxyvitamin d3, 19356-17-3, 25-hydroxycholecalciferol, Calcifediol anhydrous, Hidroferol

Molecular Formula

C₂₇H₄₄O₂

Molecular Weight

400.6 g/mol

InChI Key

JWUBBDSIWDLEOM-DTOXIADCSA-N

FDA UNII

T0WXW8F54E

The major circulating metabolite of VITAMIN D3. It is produced in the LIVER and is the best indicator of the body's vitamin D stores. It is effective in the treatment of RICKETS and OSTEOMALACIA, both in azotemic and non-azotemic patients. Calcifediol also has mineralizing properties.

Calcifediol anhydrous is a Vitamin D3 Analog.

1 2D Structure

Calcifediol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

2.1.2 InChI

InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1

2.1.3 InChI Key

JWUBBDSIWDLEOM-DTOXIADCSA-N

2.1.4 Canonical SMILES

CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C

2.1.5 Isomeric SMILES

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C

2.2 Other Identifiers

2.2.1 UNII

T0WXW8F54E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 25 Hydroxycholecalciferol

2. 25 Hydroxycholecalciferol Monohydrate

3. 25 Hydroxyvitamin D 3

4. 25 Hydroxyvitamin D3

5. 25-hydroxycholecalciferol

6. 25-hydroxycholecalciferol Monohydrate

7. 25-hydroxyvitamin D 3

8. 25-hydroxyvitamin D3

9. Anhydrous, Calcifediol

10. Calcidiol

11. Calcifediol Anhydrous

12. Calcifediol, (3 Alpha,5z,7e)-isomer

13. Calcifediol, (3 Beta,5e,7e)-isomer

14. Calderol

15. Dedrogyl

16. Hidroferol

17. Monohydrate, 25-hydroxycholecalciferol

2.3.2 Depositor-Supplied Synonyms

1. Calcidiol

2. 25-hydroxyvitamin D3

3. 19356-17-3

4. 25-hydroxycholecalciferol

5. Calcifediol Anhydrous

6. Hidroferol

7. 25-hydroxyvitamin D

8. Calderol

9. Didrogyl

10. Calcifediolum

11. Rayaldee

12. Ro 8-8892

13. 5,6-cis-25-hydroxyvitamin D3

14. Calcifediol [inn]

15. Cholecalciferol, 25-hydroxy-

16. Chebi:17933

17. (3s,5z,7e)-9,10-secocholesta-5,7,10-triene-3,25-diol

18. T0wxw8f54e

19. 3-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexanol

20. Ncgc00161326-04

21. Calcifidiol

22. Delakmin

23. 25-hydroxy Vitamin D3

24. (3beta,5z,7e)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol

25. (5z,7e)-(3s)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol

26. U-32070e

27. U 32070 E

28. 25-hydroxyvitamin D3 / 25-hydroxycholecalciferol / Calcidiol

29. 25-hydroxycholescalciferol

30. Calcifediolum [inn-latin]

31. Rovimix Hy-d

32. (1s,3z)-3-{2-[(1r,3as,4e,7ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1h-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

33. (3b,5z,7e)- 9,10-secocholesta-5,7,10(19)-triene-3,25-diol

34. Vitamin D, 25-hydroxy-

35. Hy-d

36. (1s,3z)-3-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

37. 36149-00-5

38. 25-(oh)vitamin D3

39. 5,6-trans-25-hydroxycholescalciferol

40. Unii-t0wxw8f54e

41. Ryaldee

42. Bml2-e02

43. (5z,7e)-(3s)-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol

44. 25(oh)d3

45. Einecs 242-990-9

46. Mfcd00867077

47. U 32070e

48. Calcifediol [mi]

49. (5z,7e)-9,10-seco-5,7,10(19)-cholestatrien-3beta,25-diol

50. 5,6-trans-9,10-seco-5,7,10(19)-cholestatrien-3beta,25-diol

51. Spectrum5_001931

52. Dsstox_cid_2721

53. 25-hydroxy-cholecalciferol

54. Calcifediol,anhydrous

55. Schembl3296

56. Chembl1040

57. Dsstox_rid_76699

58. Dsstox_gsid_22721

59. Bspbio_001411

60. Calcifediol, Anhydrous

61. (3s,5z,7e)-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol

62. Gtpl6921

63. Dtxsid0022721

64. Chebi:94743

65. Amy2863

66. Bcpp000306

67. Dm100

68. Hms1361g13

69. Hms1791g13

70. Hms1989g13

71. Hms2089l21

72. Hms3402g13

73. 64719-49-9

74. Act06833

75. Zinc4474414

76. Tox21_111987

77. (3s,5z,7e)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol

78. 9,10-secocholesta-5,7,10(19)-triene-3,25-diol, (3beta,5z,7e)-

79. Bdbm50521013

80. Calcifediol,anhydrous [vandf]

81. Lmst03020246

82. S1469

83. Akos015965097

84. Bcp9000472

85. Ccg-268657

86. Cs-0800

87. Db00146

88. Idi1_033881

89. Ncgc00161326-01

90. Ac-31367

91. Hy-32351

92. Cas-19356-17-3

93. 25-hydroxycholecalciferol, >=98% (hplc)

94. C01561

95. Ab01275461-01

96. Ab01275461_02

97. 356c173

98. A923587

99. Q139307

100. Sr-05000001468

101. Sr-05000001468-1

102. W-201718

103. 25-hydroxyvitamin D3 Monohydrate, >=99.0% (hplc)

104. 9,10-secocholesta-5,7,10(19)-triene-3b,25-diol

105. Brd-k77175907-001-01-5

106. B91135ec-8937-4d8b-a533-ccd82f33c1b0

107. Calcifediol, European Pharmacopoeia (ep) Reference Standard

108. (5e,7e)-9,10-secocholesta-5,7,10(19)-triene-3beta,25-diol

109. 25-hydroxyvitamin D3 Solution, 100 Mug/ml In Ethanol, 98% (cp)

110. 25-hydroxyvitamin D3 Solution, 5 Mug/ml In Ethanol, 98% (cp)

111. 25-hydroxyvitamin D3 Solution, 50 Mug/ml In Ethanol, 98% (cp)

112. Calcifediol, United States Pharmacopeia (usp) Reference Standard

113. (3s,5z,14beta,17alpha)-9,10-secocholesta-5,7,10-triene-3,25-diol

114. (5z,7e)-9,10-secocholesta-5,7,10(19)-triene-3b,25-diol Monohydrate

115. 9,10-secocholesta-5,7,10(19)-triene-1,25-diol, (3.beta,.5z,7e)-

116. (?r,1r,3as,4e,7ar)-4-[(2z)-2-[(5s)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-?,?,?,7a-tetramethyl-1h-indene-1-pentanol

117. (1s,3z)-3-[(2e)-2-[(1r,3as,7ar)-1-[(1r)-5-hydroxy-1,5-dimethyl-hexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol

118. (s,z)-3-((e)-2-((1r,3as,7ar)-1-((r)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1h-inden-4(2h)-ylidene)ethylidene)-4-methylenecyclohexanol

119. 1h-indene-1-pentanol, Octahydro-4-[(2z)-2-[(5s)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-.alpha.,.alpha.,.epsilon.,7a-tetramethyl-, (.epsilon.r,1r,3as,4e,7ar)-

120. 25-hydroxyvitamin D3 Solution, 100 Mug/ml In Ethanol, Ampule Of 1 Ml, Certified Reference Material

121. 25-hydroxyvitamin D3 Solution, 5 Mug/ml In Ethanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₄₄O₂
Molecular Weight	400.6 g/mol
XLogP3	6.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Exact Mass	400.334130642 g/mol
Monoisotopic Mass	400.334130642 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	655
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used to treat vitamin D deficiency or insufficiency, refractory rickets (vitamin D resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. Also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis.

Treatment of secondary hyperparathyroidism (SHPT)

5 Pharmacology and Biochemistry

5.1 Pharmacology

Calcidiol is the precursor of vitamin D3. Vitamin D3 is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of vitamin A. The classical manifestations of vitamin D deficiency is rickets, which is seen in children and results in bony deformaties including bowed long bones. Deficiency in adults leads to the disease osteomalacia. Both rickets and osteomalacia reflect impaired mineralization of newly synthesized bone matrix, and usually result from a combination of inadequate exposure to sunlight and decreased dietary intake of vitamin D. Common causes of vitamin D deficiency include genetic defects in the vitamin D receptor, severe liver or kidney disease, and insufficient exposure to sunlight. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma.

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.)

Vitamins

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body. (See all compounds classified as Vitamins.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CALCIFEDIOL ANHYDROUS

5.3.2 FDA UNII

T0WXW8F54E

5.3.3 Pharmacological Classes

Vitamin D3 Analog [EPC]; Cholecalciferol [CS]

5.4 ATC Code

A - Alimentary tract and metabolism

A11 - Vitamins

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

A11CC - Vitamin d and analogues

A11CC06 - Calcifediol

H - Systemic hormonal preparations, excl. sex hormones and insulins

H05 - Calcium homeostasis

H05B - Anti-parathyroid agents

H05BX - Other anti-parathyroid agents

H05BX05 - Calcifediol

5.5 Absorption, Distribution and Excretion

Absorption

Readily absorbed.

5.6 Metabolism/Metabolites

Calcidiol undergoes hydroxylation in the mitochondria of kidney tissue, and this reaction is activated by the renal 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to produce calcitriol (1,25- dihydroxycholecalciferol), the active form of vitamin D3.

5.7 Biological Half-Life

288 hours

5.8 Mechanism of Action

Calcidiol is transformed in the kidney by 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to calcitriol, the active form of vitamin D3. Calcitriol binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.

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