Maxacalcitol

Names

[ Name ]:
Maxacalcitol

[Synonym ]:
Oxarol
(1R,3S,5Z)-4-Methylene-5-[(2E)-2-[(1S,3aS,7aS)-octahydro-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol
(1S,3R,5Z,7E,20S)-20-(3-hydroxy-3-methylbutoxy)-9,10-secopregna-5,7,10-triene-1,3-diol
1α,25-Dihydroxy-22-oxavitamin D3
MC 1275
Maxacalcitol
(1S,3R,5Z,7E,9ξ)-20-(3-hydroxy-3-methylbutoxy)-9,10-secopregna-5,7,10-triene-1,3-diol
1,25-dihydroxy-22-oxavitamin D3
22-Oxacalcitriol
(1S,3R,5Z,7E,9ξ,20S)-20-(3-Hydroxy-3-methylbutoxy)-9,10-secopregna-5,7,10-triene-1,3-diol
1,3-cyclohexanediol, 4-methylene-5-[(2E)-2-[(1S,3aS,7aS)-octahydro-1-[1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,3S,5Z)-
Prezios
(1S-(1a(R*),3ab,4E(1S*,3R*,5Z),7aa))-4-Methylene-5-(2-(octahydro-1-(1-(3-hydroxy-3-methylbutoxy)ethyl)-7a-methyl-4H-inden-4-ylidene)ethylidene)-1,3-cyclohexanediol
22-Oxa-1,25-dihydroxyvitamin D3
1alpha,25-Dihydroxy-22-oxavitamin D3
1R,25-dihydroxy-22-oxavitamin D3
1a,25-Dihydroxy-22-oxavitamin D3
1,3-Cyclohexanediol, 4-methylene-5-[(2E)-2-[(1S,3aS,7aS)-octahydro-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,3S,5Z)-

Biological Activity

[Description]:

Maxacalcitol (22-Oxacalcitriol) is non-calcemic vitamin D3 analog and ligand of VDR-like receptors. IC50 value:Target: Maxacalcitol (22-Oxacalcitriol)suppresses parathyroid hormone (PTH) mRNA expression in vitro and in vivo. Maxacalcitol exhibits similar effects to calcitriol in osteoblast-like cells. Maxacalcitol(22-Oxacalcitriol) inhibits tumor growth of osteosarcoma in vitro in combination with all-trans retinoic acid.

[Related Catalog]:

Signaling Pathways >> Vitamin D Related >> VD/VDR

Research Areas >> Metabolic Disease

[References]

[1]. Barroga, et al. Inhibitory effects of 22-oxa-calcitriol and all-trans retinoic acid on the growth of a canine osteosarcoma derived cell-line in vivo and its pulmonary metastasis in vivo. Res.Vet.Sci. (2000)68 79.

[2]. Monier-Faugere, et al. 22-Oxacalcitriol suppresses secondary hyperparathyroidism without inducing low bone turnover in dogs with renal failure. Kidney Int. (1999)55 821.

[3]. Inoue K, et al. Maxacalcitol ameliorates tubulointerstitial fibrosis in obstructed kidneys by recruiting PPM1A/VDR complex to pSmad3.Lab Invest. 2012 Aug 27.

[4]. Karashima T, et al. Successful Treatment of Bowen's Disease with Topical Maxacalcitol.Acta Derm Venereol. 2012 Jan 26.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
581.4±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₆H₄₂O₄

[ Molecular Weight ]:
418.609

[ Flash Point ]:
305.4±30.1 °C

[ Exact Mass ]:
418.308319

[ PSA ]:
69.92000

[ LogP ]:
4.38

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.549

[ Storage condition ]:
2-8℃

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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