CHEBI:4712 - doxercalciferol

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ChEBI Name doxercalciferol
ChEBI ID CHEBI:4712
Definition A hydroxy seco-steroid and synthetic vitamin D2 analogue that undergoes metabolic activation in vivo to form 1α,25-dihydroxyvitamin D2 (1α,25-(OH)2D2), a naturally occurring, biologically active form of vitamin D2. It is used to treat secondary hyperparathyroidism, a condition in which the body produces excess parathyroid hormone (PTH; a natural substance needed to control the amount of calcium in the blood) in certain people with chronic kidney disease.
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Formula C28H44O2
Net Charge 0
Average Mass 412.649
Monoisotopic Mass 412.334
InChI InChI=1S/C28H44O2/c1-18(2)19(3)9-10-20(4)25-13-14-26-22(8-7-15-28(25,26)6)11-12-23-16-24(29)17-27(30)21(23)5/h9-12,18-20,24-27,29-30H,5,7-8,13-17H2,1-4,6H3/b10-9+,22-11+,23-12-/t19-,20+,24+,25+,26-,27-,28+/m0/s1
InChIKey HKXBNHCUPKIYDM-CGMHZMFXSA-N
SMILES C1[C@]2([C@](/C(=C/C=C/3\C([C@H](C[C@@H](C3)O)O)=C)/CC1)(CC[C@@]2([C@H](C)/C=C/[C@@H](C(C)C)C)[H])[H])C
Roles Classification
Biological Role(s): provitamin
A substance that can be converted into a vitamin by animal tissues.
prohormone
Any intra-glandular substance that acts as a precursor of a hormone, usually having minimal hormonal effect itself. Prohormones generally help in amplifying the effect of existing hormones.
fat-soluble vitamin
Vitamins like A, D, E and K that dissolve in fats and are stored in body tissues. Unlike the water-soluble vitamins, these are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
(via vitamin D )
Application(s): bone density conservation agent
An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.
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ChEBI Ontology
Outgoing doxercalciferol (CHEBI:4712) has role bone density conservation agent (CHEBI:50646)
doxercalciferol (CHEBI:4712) has role prohormone (CHEBI:71212)
doxercalciferol (CHEBI:4712) has role provitamin (CHEBI:50188)
doxercalciferol (CHEBI:4712) is a hydroxy seco-steroid (CHEBI:36853)
doxercalciferol (CHEBI:4712) is a vitamin D (CHEBI:27300)
IUPAC Name
(1S,3R,5Z,7E,22E)-9,10-secoergosta-5,7,10,22-tetraene-1,3-diol
INNs Sources
doxercalciferol ChemIDplus
doxercalciferol WHO MedNet
doxercalciférolum WHO MedNet
doxercalciferolum WHO MedNet
Synonyms Sources
1α-hydroxyergocalciferol ChemIDplus
1α-hydroxyvitamin D2 ChEBI
1α-hydroxyvitamin D2 UniProt
Brand Name Source
Hectorol KEGG DRUG
Manual Xrefs Databases
957 DrugCentral
C08211 KEGG COMPOUND
D01009 KEGG DRUG
DB06410 DrugBank
Doxercalciferol Wikipedia
V2H PDBeChem
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Registry Number Type Source
54573-75-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12227689 PubMed citation Europe PMC
12834181 PubMed citation Europe PMC
17603751 PubMed citation Europe PMC
21155068 PubMed citation Europe PMC
21849802 PubMed citation Europe PMC
22123370 PubMed citation Europe PMC
23780943 PubMed citation Europe PMC
25774916 PubMed citation Europe PMC
28586017 PubMed citation Europe PMC
Last Modified
10 April 2018