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

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Structure
CAS No.
104121-92-8
Chemical Name:
2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3
Synonyms
ED-71;Idecalcitol;Eldecalcitol;El calciditol;Eldecalcitol CRS;Aidit, calcitriol;Eldecalcitol(ED-71);2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3;1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3;104121-92-8 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3
CBNumber:
CB71319007
Molecular Formula:
C30H50O5
Molecular Weight:
490.71
MOL File:
104121-92-8.mol
MSDS File:
SDS
Modify Date:
2024/7/8 20:25:11

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

Melting point 126-128℃
Boiling point 655.7±55.0 °C(Predicted)
Density 1.10
storage temp. Store at -20°C
solubility Soluble in DMSO
form Powder
pka 13.80±0.60(Predicted)
color White to off-white
InChIKey FZEXGDDBXLBRTD-AYIMTCTASA-N
SMILES [C@@H]1(O)C/C(=C/C=C2\CCC[C@@]3(C)[C@@]\2([H])CC[C@@H]3[C@H](C)CCCC(O)(C)C)/C(=C)[C@@H](O)[C@@H]1OCCCO

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Chemical Properties,Uses,Production

Description

Eldecalcitol (Edirol) was approved in January 2011 by the Japanese Ministry of Health, Labor, and Welfare for the treatment of osteoporosis. Because of vitamin D’s central role in the bone health, vitamin D and analogs of vitamin D have been used to treat patients diagnosed with osteoporosis. Eldecalcitol is an analog of the active form of vitamin D, calcitriol, in which the lower cyclohexane ring contains a hydroxypropyl group. The synthesis of eldecalcitol involves the assembly of two units, a fully protected (3S,4S,5R)-oct-1-en-7-yne-3,4,5-triol and a fused bicyclic system, (R)-6- ((1R,3aR,7aR,E)-4-(bromomethylene)-7a-methyloctahydro-1H-inden-1- yl)-2-methylheptan-2-ol, through a Diels-Alder reaction to give fully protected eldecalcitol. The hydroxyl groups are then deprotected to give the parent molecule. Eldecalcitol binds to the vitaminDreceptor 2.7-fold more potently than calcitriol, while only weakly inhibiting serum parathyroid hormone.

Uses

Eldecalcitol is a derivative of vitamin D3 (V676045) which is the vitamin that mediates intestinal calcium absorbtion, bone calcium metabolism and probably, muscle activity.

Definition

ChEBI: A hydroxycalciol that is calcitriol with a 3-hydroxypropoxy group at position 2.

Clinical Use

Eldecalcitol is a vitamin D3 analog approved in Japan for the treatment of osteoporosis. Itwasdiscoveredby Chugai and co-developed with Taisho. Eldecalcitol, a hormonally active calcitrol analog, regulates calcium and bone metabolism. The drug was approved on the basis of results from randomized, double-blinded, parallelgroup, phase III studies taking place over three years that showed eldecalcitol to significantly lower incidence of new vertebral fractures compared to those receiving the comparator drug alfacalcidol. Discovery and SAR studies of vitamin D3 analogs leading to the identification of eldecalcitol have been reported. In addition, multiple syntheses, including parallel approaches, have been reported in publications and patents.

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Preparation Products And Raw materials

Raw materials

Preparation Products

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2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Eldecalcitol ED-71 (1R,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 1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 Eldecalcitol(ED-71) 2.beta.-(3-Hydroxypropoxy)-1.alpha.,25-dihydroxyvitaMin D3 (1S,2S,3S,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 El calciditol Eldecalcitol {2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3} 1,3-Cyclohexanediol, 2-(3-hydroxypropoxy)-4-methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,2R,3R,5Z)- (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 104121-92-8 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 (1R,2R,3R,Z)-5-((E)-2-((1R,3aS,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 CRS Aidit, calcitriol Idecalcitol 104121-92-8 04121-92-8