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Doxercalciferol

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Chemistry

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Also known as: 54573-75-0, Hectorol, 1-hydroxyergocalciferol, 1alpha-hydroxyergocalciferol, Tsa 840, 1alpha-hydroxyvitamin d2

Molecular Formula

C₂₈H₄₄O₂

Molecular Weight

412.6 g/mol

InChI Key

HKXBNHCUPKIYDM-CGMHZMFXSA-N

FDA UNII

3DIZ9LF5Y9

Doxercalciferol is a synthetic analog of vitamin D with potential antineoplastic activity. In the liver, doxercalciferol is converted to its biologically active vitamin D metabolites, which control the intestinal absorption of dietary calcium, the tubular reabsorption of calcium by the kidney and, in conjunction with parathyroid hormone (PTH), the mobilization of calcium from the skeleton. Through interaction with specific receptor proteins in target tissues, these vitamin D metabolites act directly on osteoblasts to stimulate skeletal growth, and on the parathyroid glands to suppress PTH synthesis and secretion. This agent has also been shown to inhibit the growth of retinoblastomas, and may exhibit some antiproliferative activity against prostate cancer cells.

Doxercalciferol is a Vitamin D2 Analog.

1 2D Structure

Doxcercalciferol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

2.1.2 InChI

InChI=1S/C28H44O2/c1-18(2)19(3)9-10-20(4)25-13-14-26-22(8-7-15-28(25,26)6)11-12-23-16-24(29)17-27(30)21(23)5/h9-12,18-20,24-27,29-30H,5,7-8,13-17H2,1-4,6H3/b10-9+,22-11+,23-12-/t19-,20+,24+,25+,26-,27-,28+/m0/s1

2.1.3 InChI Key

HKXBNHCUPKIYDM-CGMHZMFXSA-N

2.1.4 Canonical SMILES

CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C

2.1.5 Isomeric SMILES

C[C@H](/C=C/[C@H](C)C(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

3DIZ9LF5Y9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1 Alpha-hydroxyergocalciferol

2. 1alpha(oh)2d2

3. 1alpha-hydroxyvitamin D2

4. 1alpha-ohd2

5. Doxacalciferol

6. Hectorol

2.3.2 Depositor-Supplied Synonyms

1. 54573-75-0

2. Hectorol

3. 1-hydroxyergocalciferol

4. 1alpha-hydroxyergocalciferol

5. Tsa 840

6. 1alpha-hydroxyvitamin D2

7. 1-alpha-hydroxyvitamin D2

8. 1-alpha-hydroxyergocalciferol

9. 1-hydroxyvitamin D2

10. 1.alpha.-hydroxyvitamin D2

11. 1alpha-oh-d2

12. (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-1-[(e,2r,5r)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

13. 3diz9lf5y9

14. (1s,3r,5z,7e,22e)-9,10-secoergosta-5,7,10,22-tetraene-1,3-diol

15. 1.alpha.-hydroxyergocalciferol

16. Chebi:4712

17. 1-.alpha.-hydroxyergocalciferol

18. Tsa-840

19. Gz427397

20. Doxercalciferol [inn]

21. 1alpha-hydroxyvitamin D2 / 1alpha-hydroxyergocalciferol

22. (5z,7e,22e)-(1s,3r)-9,10-seco-5,7,10(19),22-ergostatetraene-1,3-diol

23. Hectorol (tn)

24. (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(e,1r,4r)-1,4,5-trimethylhex-2-enyl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylene-cyclohexane-1,3-diol

25. Vitamin D2, 1alpha-hydroxy-

26. Unii-3diz9lf5y9

27. Brn 4716774

28. Doxercalciferol [usan:inn]

29. Doxercalciferolum

30. Ncgc00182058-03

31. 1alphaohd2

32. Mfcd00871065

33. 1a-hydroxyvitamin D2

34. 1alpha-hydroxy Vitamin D2

35. (5z,7e,22e)-9,10-secoergosta-5,7,10(19),22-tetraene-1alpha,3beta-diol

36. Vitamin D2, 1a-hydroxy-

37. 1-alpha-hydroxy-vitamin D2

38. Doxercalciferol [mi]

39. Dsstox_cid_14214

40. Dsstox_rid_79125

41. Doxercalciferol (usan/inn)

42. Dsstox_gsid_34214

43. Doxercalciferol [usan]

44. Schembl322422

45. Doxercalciferol [vandf]

46. Gtpl2790

47. Doxercalciferol [mart.]

48. 1-alpha-hydroxyvitamind2

49. Chembl1200810

50. Doxercalciferol [usp-rs]

51. Doxercalciferol [who-dd]

52. Dtxsid1034214

53. Act06836

54. Ex-a4428

55. Zinc4641374

56. Tox21_112978

57. Doxercalciferol [orange Book]

58. Hsci1_000341

59. Lmst03010028

60. Akos005146517

61. Cs-0395

62. Db06410

63. Doxercalciferol [usp Monograph]

64. 9,10-secoergosta-5,7,10(19),22-tetraene-1,3-diol, (1-alpha,3-beta,5z,7e,22e)-

65. 9,10-secoergosta-5,7,10(19),22-tetraene-1,3-diol, (1.alpha.,3.beta.,5z,7e,22e)-

66. Bs-17040

67. Hy-32348

68. Cas-54573-75-0

69. 1a-hydroxyergocalciferol (ercalcidol)

70. C08211

71. D01009

72. D82103

73. 573d750

74. Q5303688

75. Doxercalciferol, >=98% (hplc), Solubility: >10 Mg/ml In Dmso

76. Doxercalciferol, United States Pharmacopeia (usp) Reference Standard

77. (5z,7e,22e)-9,10-secoergosta-5,7,10(19),22-tetraene-1.alpha.,3.beta.-diol

78. 7,10(19),22-tetraene-1,3-diol,(1-alpha,3-beta,5z,7e,22e)-10-secoergosta-5

79. 9,10-secoergosta-5,7,10(19),22-tetraene-1,3-diol, (1alpha,3beta,5z,7e,22e)-

80. (1r,3s,5z)-4-methylene-5-[(2e)-2-[(1r,3as,7ar)-octahydro-7?-methyl-1-[(1r,2e)-1,4,5-trimethyl-2-hexen-1-yl]-4h-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol

81. (1r,3s,z)-5-((e)-2-((1r,3as,7ar)-1-((2r,5r,e)-5,6-dimethylhept-3-en-2-yl)-7a-methyldihydro-1h-inden-4(2h,5h,6h,7h,7ah)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol

82. (1r,3s,z)-5-((e)-2-((1r,3as,7ar)-1-((2r,5r,e)-5,6-dimethylhept-3-en-2-yl)-7a-methylhexahydro-1h-inden-4(2h)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol

83. 1,3-cyclohexanediol, 4-methylene-5-((2e)-2-((1r,3as,7ar)-octahydro-7a-methyl-1-((1r,2e)-1,4,5-trimethyl-2-hexen-1-yl)-4h-inden-4-ylidene)ethylidene)-, (1r,3s,5z)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₄₄O₂
Molecular Weight	412.6 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	412.334130642 g/mol
Monoisotopic Mass	412.334130642 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	712
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Doxercalciferol
PubMed Health	Doxercalciferol
Drug Classes	Calcium Regulator, Endocrine-Metabolic Agent, Nutriceutical, Nutritive Agent
Drug Label	Doxercalciferol is a synthetic vitamin D2 analog that undergoes metabolic activation in vivo to form 1,25-dihydroxyvitamin D2 (1,25-(OH)2D2), a naturally occurring, biologically active form of vitamin D2. Doxercalciferol injection is supplied in...
Active Ingredient	Doxercalciferol
Dosage Form	Injectable; Capsule
Route	injection; Injection; Oral
Strength	0.5mcg; 4mcg/2ml (2mcg/ml); 2mcg/ml; 1mcg; 2.5mcg
Market Status	Tentative Approval; Prescription
Company	Cobrek Pharma; Sandoz; Hikma Pharms; Roxane

2 of 4
Drug Name	Hectorol
PubMed Health	Doxercalciferol
Drug Classes	Calcium Regulator, Endocrine-Metabolic Agent, Nutriceutical, Nutritive Agent
Drug Label	Doxercalciferol, the active ingredient in Hectorol, is a synthetic vitamin D2 analog that undergoes metabolic activation in vivo to form 1,25-dihydroxyvitamin D2 (1,25-(OH)2D2), a naturally occurring, biologically active form of vitamin D2. H...
Active Ingredient	Doxercalciferol
Dosage Form	Capsule; Injectable
Route	Injection; Oral
Strength	0.5mcg; 1mcg; 2mcg/ml (2mcg/ml); 4mcg/2ml (2mcg/ml); 2.5mcg
Market Status	Prescription
Company	Genzyme

3 of 4
Drug Name	Doxercalciferol
PubMed Health	Doxercalciferol
Drug Classes	Calcium Regulator, Endocrine-Metabolic Agent, Nutriceutical, Nutritive Agent
Drug Label	Doxercalciferol is a synthetic vitamin D2 analog that undergoes metabolic activation in vivo to form 1,25-dihydroxyvitamin D2 (1,25-(OH)2D2), a naturally occurring, biologically active form of vitamin D2. Doxercalciferol injection is supplied in...
Active Ingredient	Doxercalciferol
Dosage Form	Injectable; Capsule
Route	injection; Injection; Oral
Strength	0.5mcg; 4mcg/2ml (2mcg/ml); 2mcg/ml; 1mcg; 2.5mcg
Market Status	Tentative Approval; Prescription
Company	Cobrek Pharma; Sandoz; Hikma Pharms; Roxane

4 of 4
Drug Name	Hectorol
PubMed Health	Doxercalciferol
Drug Classes	Calcium Regulator, Endocrine-Metabolic Agent, Nutriceutical, Nutritive Agent
Drug Label	Doxercalciferol, the active ingredient in Hectorol, is a synthetic vitamin D2 analog that undergoes metabolic activation in vivo to form 1,25-dihydroxyvitamin D2 (1,25-(OH)2D2), a naturally occurring, biologically active form of vitamin D2. H...
Active Ingredient	Doxercalciferol
Dosage Form	Capsule; Injectable
Route	Injection; Oral
Strength	0.5mcg; 1mcg; 2mcg/ml (2mcg/ml); 4mcg/2ml (2mcg/ml); 2.5mcg
Market Status	Prescription
Company	Genzyme

4.2 Drug Indication

Doxercalciferol is indicated for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis, as well as for the treatment of secondary hyperparathyroidism in patients with Stage 3 or Stage 4 chronic kidney disease.

FDA Label

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

DOXERCALCIFEROL

5.2.2 FDA UNII

3DIZ9LF5Y9

5.2.3 Pharmacological Classes

Vitamin D2 Analog [EPC]; Ergocalciferols [CS]

5.3 ATC Code

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

H05 - Calcium homeostasis

H05B - Anti-parathyroid agents

H05BX - Other anti-parathyroid agents

H05BX03 - Doxercalciferol

5.4 Metabolism/Metabolites

Doxercalciferol is absorbed from the gastrointestinal tract and activated by CYP 27 in the liver to form 1,25-(OH)2D2 (major metabolite) and 1,24-dihydroxyvitamin D2 (minor metabolite). Activation of doxercalciferol does not require the involvement of the kidneys.

5.5 Biological Half-Life

32 to 37 hours.

5.6 Mechanism of Action

Calcitriol (1,25-(OH)2D3) and 1,25-(OH)2D2 regulate blood calcium at levels required for essential body functions. Specifically, the biologically active vitamin D metabolites control the intestinal absorption of dietary calcium, the tubular reabsorption of calcium by the kidney and, in conjunction with parathyroid hormone (PTH), the mobilization of calcium from the skeleton. They act directly on bone cells (osteoblasts) to stimulate skeletal growth, and on the parathyroid glands to suppress PTH (parathyroid hormone) synthesis and secretion. These functions are mediated by the interaction of these biologically active metabolites with specific receptor proteins in the various target tissues. In patients with chronic kidney disease (CKD), deficient production of biologically active vitamin D metabolites (due to lack of or insufficient 25-hydroxyvitamin D-1-alpha-hydroxylase activity) leads to secondary hyperparathyroidism, which contributes to the development of metabolic bone disease.

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15 API Suppliers

10 USDMF

2 EU WC

4 NDC API

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FINISHED DOSAGE FORMULATIONS

35 FDF Dossiers

33 FDA Orange Book

2 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

INJECTABLE;INJECTION - 10MCG/5ML (2MCG/ML)

INJECTABLE;INJECTION - 4MCG/2ML (2MCG/ML)

CAPSULE;ORAL - 0.5MCG

CAPSULE;ORAL - 1MCG

CAPSULE;ORAL - 2.5MCG

RELATED EXCIPIENT COMPANIES

7 DKSH

2 Nanjing Well Pharmaceutical

4 ACG Worldwide

4 Actylis

3 BASF

1 Finar

1 Gangwal Chemicals

1 Kerry

3 Lonza Capsugel

1 Pluviaendo

1 Qualicaps

2 Roquette

3 Seppic

1 Valens Pharmachem

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3 Coloring Agents

2 Surfactant & Foaming Agents

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