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Eldecalcitol

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Also known as: Edirol, Ed-71, 104121-92-8, 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin d3, I2jp8ue90h, (1r,2r,3r,5z)-5-[(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]-2-(3-hydroxypropoxy)-4-methylidenecyclohexane-1,3-diol

Molecular Formula

C₃₀H₅₀O₅

Molecular Weight

490.7 g/mol

InChI Key

FZEXGDDBXLBRTD-AYIMTCTASA-N

FDA UNII

I2JP8UE90H

Eldecalcitol (ED-71), a vitamin D analog, is a more potent inhibitor of bone resorption than alfacalcidol in an estrogen-deficient rat model of osteoporosis. Eldecalcitol, effectively and safely increased lumbar and hip bone mineral density (BMD) in osteoporotic patients who also received vitamin D3 supplementation.

1 2D Structure

Eldecalcitol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2R,3R,5Z)-5-[(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]-2-(3-hydroxypropoxy)-4-methylidenecyclohexane-1,3-diol

2.1.2 InChI

InChI=1S/C30H50O5/c1-20(9-6-15-29(3,4)34)24-13-14-25-22(10-7-16-30(24,25)5)11-12-23-19-26(32)28(27(33)21(23)2)35-18-8-17-31/h11-12,20,24-28,31-34H,2,6-10,13-19H2,1,3-5H3/b22-11+,23-12-/t20-,24-,25+,26-,27-,28-,30-/m1/s1

2.1.3 InChI Key

FZEXGDDBXLBRTD-AYIMTCTASA-N

2.1.4 Canonical SMILES

CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(C(C(C3=C)O)OCCCO)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]([C@H]([C@@H](C3=C)O)OCCCO)O)C

2.2 Other Identifiers

2.2.1 UNII

I2JP8UE90H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

2. 2-(3-hydroxypropoxy)calcitriol

3. 20-epi-1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3

4. 20-epi-ed-71

5. 20-epi-eldecalcitol

6. Ed 71

7. Ed-71

2.3.2 Depositor-Supplied Synonyms

1. Edirol

2. Ed-71

3. 104121-92-8

4. 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

5. I2jp8ue90h

6. (1r,2r,3r,5z)-5-[(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]-2-(3-hydroxypropoxy)-4-methylidenecyclohexane-1,3-diol

7. 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3

8. Ed 71

9. (5z,7e)-(1r,2r,3r)-2-(3-hydroxypropoxy)-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol

10. 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)cholecalciferol

11. (1r,2r,3r,5z,7e,14beta,17alpha)-2-(3-hydroxypropoxy)-9,10-secocholesta-5,7,10-triene-1,3,25-triol

12. 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 / 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)cholecalciferol

13. Eldecalcitol [inn]

14. 2-(3-hydroxypropoxy)calcitriol

15. Eldecalcitol [inn:jan]

16. Unii-i2jp8ue90h

17. Hy-a0020

18. Edirol (tn)

19. Eldecalcitol (jan/inn)

20. Eldecalcitol [mi]

21. Eldecalcitol [jan]

22. Eldecalcitol [mart.]

23. Eldecalcitol [who-dd]

24. Gtpl2783

25. Schembl5457151

26. Chembl4297608

27. Chebi:73927

28. 2beta-(3-hydroxypropoxy)calcitriol

29. (1s,2s,3s,z)-5-((e)-2-((1r,7ar)-1-((r)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1h-inden-4(2h)-ylidene)ethylidene)-2-(3-hydroxypropoxy)-4-methylenecyclohexane-1,3-diol; Eldecalcitol

30. Ex-a5554

31. Zinc3934328

32. Ct-081

33. Lmst03020477

34. Akos025312299

35. Cs-0363

36. Db05295

37. 9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol, 2-(3-hydroxypropoxy)-, (1alpha,2beta,3beta,5z,7e)-

38. Ac-26354

39. D07578

40. 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)-cholecalciferol

41. (1r,2r,3r,5z,7e)-2-(3-hydroxypropoxy)-9,10-secocholesta-5,7,10-triene-1,3,25-triol

42. (5z,7e)-2.beta.-(3-hydroxypropoxy)-9,10-secocholesta-5,7,10(19)-triene-1.alpha.,3.beta.,25-triol

43. Ed9

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₅₀O₅
Molecular Weight	490.7 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	490.36582469 g/mol
Monoisotopic Mass	490.36582469 g/mol
Topological Polar Surface Area	90.2 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	784
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
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

Investigated for use/treatment in osteoporosis.

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.)

5.2 Mechanism of Action

Eldecalcitol [1a,25-DIHYDROXY-2-(3-hydroxypropoxy)vitamin D3] is an analog of 1a,25-dihydroxyvitamin D3 [1,25(OH)2D3], bearing a hydroxypropoxy residue at the 2b position. Eldecalcitol is also effective in increasing bone mass and was able to enhance bone strength in rodents. It binds to the vitamin D receptor (VDR) with less affinity but binds to vitamin D-binding protein with higher affinity than 1,25(OH)2D, showing a long half-life in plasma.

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