24,25-DIHYDROXYCHOLECALCIFEROL

Details

Stereochemistry	EPIMERIC
Molecular Formula	C27H44O3
Molecular Weight	416.6365
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 6
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure of 24,25-DIHYDROXYCHOLECALCIFEROL

Structure Search

SMILES

[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C)[C@H](C)CCC(O)C(C)(C)O

InChI

InChIKey=FCKJYANJHNLEEP-SRLFHJKTSA-N

InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25?,27-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H44O3
Molecular Weight	416.6365
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	5 / 6
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11179746
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7872065 | https://www.ncbi.nlm.nih.gov/pubmed/3093022

24-Hydroxycalcidiol (24,25-dihydroxy vitamin D3) is a circulating metabolite of vitamin D3. 24,25(OH)2D3 functions by activation of Vitamin D receprtor and promotion of ostecalcin expression, but is less effective than other D3 metabolite, 1alpha,25(OH)2D3. There is conflicting evidence on efffect of 24-hydroxycalcidiol on bone metabolism. In several animal studies it was demonstrated that 24-hydroxycalcidiol was able to stimulate calcification of bone and restore the reduction in bone mineral apposition rate. However, no beneficial effect of 24R,25(OH)2D3 treatment of postmenapausal women on bone mineral density or bone loss and calcium metabolism were observed.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin D3 receptor 9 Target ID: P11473 Gene ID: 7421.0 Gene Symbol: VDR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7872065	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Postmenopausal bone loss 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3093022	Preventing		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Importance of the stereochemical position of the 24-hydroxyl to biological activity of 24-hydroxyvitamin D3.	1975 Jul 29	1148204
The 24-hydroxylation of 1,25-dihydroxyvitamin D3.	1977 Feb 25	838723

Patents

Sample Use Guides

In Vivo Use Guide

In clinical trial for prevention of postmenapausal bone loss, 24-hydroxycalcidiol was administered orally at daily doses of 10 ug.

Route of Administration: Oral

In Vitro Use Guide

Dose-dependent induction of the human osteocalcin (hOC) gene promoter by 24R,25(OH)2D3 in the presence of 0.1% serum was demonstrated. Following transfection of pXP2hOC-838/+10 (5 ug/60 mm dish) into MC3T3-E1 cells, various concentrations of 24R,25(OH)2D3 were added, and incubation was carried out for 48 h in alpha-MEM containing 0.1% FBS. The cells were harvested and assayed for luciferase activity. 24R,25(OH)2D3 induced luciferase activity with IC50 of 7.5 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:23:04 UTC 2023` Edited by `admin` on `Sat Dec 16 05:23:04 UTC 2023`
Record UNII	0AXX2V8L5Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

24,25-DIHYDROXYCHOLECALCIFEROL

Common Name

English

24,25-DIHYDROXYVITAMIN D 3

Common Name

English

2,3-HEPTANEDIOL, 2-METHYL-6-((1R,3AS,4E,7AR)-OCTAHYDRO-4-((2Z)-2-((5S)-5-HYDROXY-2-METHYLENECYCLOHEXYLIDENE)ETHYLIDENE)-7A-METHYL-1H-INDEN-1-YL)-, (6R)-

Common Name

English

24,25-DIHYDROXYVITAMIN D3

Common Name

English

SECALCIFEROL, (24RS)-

Common Name

English

24-HYDROXYCALCIDIOL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C941