24-hydroxycalcidiol

24,25-Dihydroxycholecalciferol
	IUPAC name (6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
	Other names 24,25-dihydroxyvitamin D3; (24R)-hydroxycalcifediol; (24R)-hydroxycalcidiol
Identifiers
CAS number	40013-87-4
PubChem	6434253
ChemSpider	4939193
ChEMBL	CHEMBL47183
Jmol-3D images	Image 1
	SMILES O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCC(O)C(O)(C)C)C ;
	InChI 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 ; Key: FCKJYANJHNLEEP-SRLFHJKTSA-N InChI=1/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; Key: FCKJYANJHNLEEP-SRLFHJKTBM ;
Properties
Molecular formula	C27H44O3
Molar mass	416.63 g/mol
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

同: 24,2 5-dihydroxyvitamin D3

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/14 10:10:32」(JST)

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[Wiki en表示]

24,25-Dihydroxycholecalciferol, also known as 24,25-dihydroxyvitamin D₃ and (24R)-hydroxycalcidiol (abbreviated as 24(R),25-(OH)₂D₃),^[1] is a compound which is closely related to 1,25-dihydroxyvitamin D₃, the active form of vitamin D₃, but like vitamin D₃ itself and 25-hydroxyvitamin D₃ is inactive as a hormone both in vitro^[2] and in vivo.^[3] It was identified by Michael F. Holick.^[4]

Formation and significance[edit]

24,25-dihydroxyvitamin D₃ is formed from 25-hydroxyvitamin D₃ by the action of P450cc24 (25-hydroxyvitamin D3-24-hydroxylase), which appears to be "a multicatalytic enzyme catalyzing most, if not all, of the reactions in the C-24/C-23 pathway of 25-OH-D3 metabolism."^[5] It has been proposed that 24,25-dihydroxyvitamin D₃ is a metabolite of 25-hydroxyvitamin D₃ which is destined for excretion.^[5]

It is not known whether the compound might also have some physiologically significant activity. Some evidence of a possible receptor has been obtained.^[6]

Interactive pathway map[edit]

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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Vitamin D Synthesis Pathway edit

^ The interactive pathway map can be edited at WikiPathways: "VitaminDSynthesis_WP1531".

References[edit]

^ "Nomenclature of Vitamin D. Recommendations 1981. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN)" reproduced at the Queen Mary, University of London website. Retrieved 21 March 2010.
^ Sørnes, S.; Bjøro, T.; Berg, J. P.; Torjesen, P. A.; Haug, E. (1994). "Calcitriol attenuates the basal and vasoactive intestinal peptide-stimulated cAMP production in prolactin-secreting rat pituitary (GH4C1) cells". Molecular and cellular endocrinology 101 (1–2): 183–188. PMID 9397951.
^ Mortensen, B. M.; Gautvik, K. M.; Gordeladze, J. O. (1993). "Bone turnover in rats treated with 1,25-dihydroxyvitamin D3, 25-hydroxyvitamin D3 or 24,25-dihydroxyvitamin D3". Bioscience reports 13 (1): 27–39. PMID 8392394.
^ Holick, MF; Schnoes, HK; Deluca, HF; Gray, RW; Boyle, IT; Suda, T (1972). "Isolation and identification of 24,25-dihydroxycholecalciferol, a metabolite of vitamin D made in the kidney". Biochemistry 11 (23): 4251–5. doi:10.1021/bi00773a009. PMID 4342902.
^ ^a ^b Beckman, M. J.; Tadikonda, P.; Werner, E.; Prahl, J.; Yamada, S.; Deluca, H. F. (1996). "Human 25-Hydroxyvitamin D3-24-Hydroxylase, a Multicatalytic Enzyme†". Biochemistry 35 (25): 8465–8472. doi:10.1021/bi960658i. PMID 8679605.
^ Sömjen, D.; Sömjen, G. J.; Weisman, Y.; Binderman, I. (1982). "Evidence for 24,25-dihydroxycholecalciferol receptors in long bones of newborn rats". The Biochemical journal 204 (1): 31–36. PMC 1158312. PMID 6981414.

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English Journal

Evidence that both 1alpha,25-dihydroxyvitamin D3 and 24-hydroxylated D3 enhance human osteoblast differentiation and mineralization.

van Driel M1, Koedam M, Buurman CJ, Roelse M, Weyts F, Chiba H, Uitterlinden AG, Pols HA, van Leeuwen JP.
Journal of cellular biochemistry.J Cell Biochem.2006 Oct 15;99(3):922-35.
Vitamin D plays a major role in the regulation of mineral homeostasis and affects bone metabolism. So far, detailed knowledge on the vitamin D endocrine system in human bone cells is limited. Here we investigated the direct effects of 1alpha,25-(OH)2D3 on osteoblast differentiation and mineralizatio
PMID 16741965

Calcitriol attenuates the basal and vasoactive intestinal peptide-stimulated cAMP production in prolactin-secreting rat pituitary (GH4C1) cells.

Sørnes S1, Bjøro T, Berg JP, Torjesen PA, Haug E.
Molecular and cellular endocrinology.Mol Cell Endocrinol.1994 May;101(1-2):183-8.
A clonal strain of prolactin-producing rat pituitary tumour cells (GH4C1 cells) was used to study the effect of calcitriol on cyclic adenosine monophosphate (cAMP) production. Calcitriol (10 nM) attenuated both the basal and vasoactive intestinal peptide (VIP)-stimulated cAMP production after 2 days
PMID 9397951

Human pharmacokinetics of orally administered (24 R)-hydroxycalcidiol.

Leeuwenkamp OR1, van der Wiel HE, Lips P, van der Vijgh WJ, Barto R, Greuter H, Netelenbos JC.
European journal of clinical chemistry and clinical biochemistry : journal of the Forum of European Clinical Chemistry Societies.Eur J Clin Chem Clin Biochem.1993 Jul;31(7):419-26.
To gain an insight in the regulation of (24R)-hydroxycalcidiol, we studied the pharmacokinetics of orally administered (24R)-hydroxycalcidiol in 6 healthy subjects without calcium supplementation, in 4 healthy subjects with calcium supplementation and in 6 patients with primary hyperparathyroidism.
PMID 8399781

Related Pictures

También puedes ayudar wikificando otros 24,25-dihydroxycholecalciferol.png Patent WO2007012977A2 - Steroid kit and 鶏卵中の25-ヒドロキシビタミン Vitamin D Analogs in Cancer Prevention and Patent WO2008128782A2 - Photochemical

[WikiPathways-7] The interactive pathway map can be edited at WikiPathways: "VitaminDSynthesis_WP1531".

[1] "Nomenclature of Vitamin D. Recommendations 1981. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN)" reproduced at the Queen Mary, University of London website. Retrieved 21 March 2010.

[2] Sørnes, S.; Bjøro, T.; Berg, J. P.; Torjesen, P. A.; Haug, E. (1994). "Calcitriol attenuates the basal and vasoactive intestinal peptide-stimulated cAMP production in prolactin-secreting rat pituitary (GH4C1) cells". Molecular and cellular endocrinology 101 (1–2): 183–188. PMID 9397951.

[3] Mortensen, B. M.; Gautvik, K. M.; Gordeladze, J. O. (1993). "Bone turnover in rats treated with 1,25-dihydroxyvitamin D3, 25-hydroxyvitamin D3 or 24,25-dihydroxyvitamin D3". Bioscience reports 13 (1): 27–39. PMID 8392394.

[4] Holick, MF; Schnoes, HK; Deluca, HF; Gray, RW; Boyle, IT; Suda, T (1972). "Isolation and identification of 24,25-dihydroxycholecalciferol, a metabolite of vitamin D made in the kidney". Biochemistry 11 (23): 4251–5. doi:10.1021/bi00773a009. PMID 4342902.

[Beckman1996-5] Beckman, M. J.; Tadikonda, P.; Werner, E.; Prahl, J.; Yamada, S.; Deluca, H. F. (1996). "Human 25-Hydroxyvitamin D3-24-Hydroxylase, a Multicatalytic Enzyme†". Biochemistry 35 (25): 8465–8472. doi:10.1021/bi960658i. PMID 8679605.

[pmid6981414-6] Sömjen, D.; Sömjen, G. J.; Weisman, Y.; Binderman, I. (1982). "Evidence for 24,25-dihydroxycholecalciferol receptors in long bones of newborn rats". The Biochemical journal 204 (1): 31–36. PMC 1158312. PMID 6981414.

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