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Alfacalcidol

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20 API Suppliers, 4 CEP/COS, 4 JDMF, 1 KDMF, 13 Listed Suppliers, $ API Reference Price

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4 CEP/COS
4 JDMF
1 KDMF
13 Listed Suppliers
$ API Reference Price

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52 FDF Dossiers, 26 Europe, 6 Canada, 6 South Africa, 14 Listed Dossiers

52 FDF Dossiers
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6 Canada
6 South Africa
14 Listed Dossiers

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16 Finished Drug Prices

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14 APIs, 5 FDF Dossiers

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5 FDF Dossiers

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3 EDQM
1 Others

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Chemistry

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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

Alfacalcidol

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 Formula	C₂₇H₄₄O₂
Molecular Weight	400.6 g/mol
XLogP3	6.8
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	643
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
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

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.

API SUPPLIERS

01

LGM Pharma

U.S.A

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPHI Middle east

Not Confirmed

LGM Pharma accelerates & optimizes the new product pathway from early development through commercialization.

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Century Pharmaceuticals

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPHI Middle east

Not Confirmed

Century has been an API manufacturer for over 30 years & is the partner of choice for multipurpose custom manufacturing projects.

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India

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USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

03

TAPI Technology & API Services

Israel

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI WW Frankfurt

Booth #6.1A32

TAPI offers customized CDMO Solutions for API development and manufacturing services.

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DISHMAN NETHERLANDS B.V.

Netherlands

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CPHI Middle east

Not Confirmed

05

Teva Pharmaceutical Industries

Israel

India

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API Reference Price

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