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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

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11473
Gene ID: 7421.0
Gene Symbol: VDR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Importance of the stereochemical position of the 24-hydroxyl to biological activity of 24-hydroxyvitamin D3.
1975 Jul 29
The 24-hydroxylation of 1,25-dihydroxyvitamin D3.
1977 Feb 25
Patents

Sample Use Guides

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.
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
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
FDA ORPHAN DRUG 15786
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
Code System Code Type Description
PUBCHEM
6434253
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
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CAS
40013-87-4
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
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NCI_THESAURUS
C126931
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
PRIMARY NCIT
WIKIPEDIA
24,25-Dihydroxycholecalciferol
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
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FDA UNII
0AXX2V8L5Z
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
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ECHA (EC/EINECS)
254-749-5
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
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EPA CompTox
DTXSID501028177
Created by admin on Sat Dec 16 05:23:04 GMT 2023 , Edited by admin on Sat Dec 16 05:23:04 GMT 2023
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