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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H38F6O3
Molecular Weight 524.5792
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of FALECALCITRIOL

SMILES

[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)CCCC(O)(C(F)(F)F)C(F)(F)F

InChI

InChIKey=XPYGGHVSFMUHLH-UUSULHAXSA-N
InChI=1S/C27H38F6O3/c1-16(6-4-13-25(36,26(28,29)30)27(31,32)33)21-10-11-22-18(7-5-12-24(21,22)3)8-9-19-14-20(34)15-23(35)17(19)2/h8-9,16,20-23,34-36H,2,4-7,10-15H2,1,3H3/b18-8+,19-9-/t16-,20-,21-,22+,23+,24-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://link.springer.com/article/10.1007/s007740050027 http://www.ncbi.nlm.nih.gov/pubmed/15632470

Falecalcitriol is an analog of calcitriol. Falecalcitriol was first approved by Pharmaceuticals and Medicals Devices Agency of Japan (PMDA) on Apr 4, 2001. It was co-developed by Taisho, Dainippon Sumitomo and Kissei, then marketed as Hornel by Taisho and Taisho Toyama or as Fulstan by Dainippon Sumitomo Pharma and Kissei in JP. It has a higher potency both in vivo and in vitro systems, and longer duration of action in vivo. This medicine improves bone disease and symptoms caused by shortage of vitamin D, etc. It also prompts calcium absorption to supply lacked calcium and prevents bone-thinning. It is usually used to treat secondary hyperparathyroidism under maintenance dialysis, hypoparathyroidism, rickets or osteomalacia. Falecalcitriol regulates the proliferation of parathyroid cells and parathyroid hormone synthesis possibly via binding to a nuclear receptor for vitamin D (VDR). It is often not possible to administer doses high enough to sufficiently inhibit parathyroid hormones because of the risk of hypercalcemia and hyperphosphatemia.

Approval Year

Conditions
PubMed

PubMed

TitleDatePubMed
Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3.
2000 Aug
Enhanced coactivator binding and transcriptional activation of mutant vitamin D receptors from patients with hereditary 1,25-dihydroxyvitamin D-resistant rickets by phosphorylation and vitamin D analogs.
2005 Sep
Patents

Patents

Sample Use Guides

The recommended dose is 0.3 μg once daily for secondary hyperparathyroidism and 0.3-0.9 μg once daily for hypoparathyroidism, rickets or osteomalacia.
Route of Administration: Oral
In Vitro Use Guide
1,25(OH)2 D3 decreased the expression of ERbeta proteins in smooth muscle cells and increased the ERalpha isoform in E304 cells by 40% to 75%
Name Type Language
FALECALCITRIOL
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
FALECALCITRIOL [JAN]
Common Name English
Falecalcitriol [WHO-DD]
Common Name English
falecalcitriol [INN]
Common Name English
FALECALCITORIOL
JAN  
Common Name English
FALECALCITORIOL [JAN]
Common Name English
(+)-(5Z,7E)-26,26,26,27,27,27-HEXAFLUORO-9,10-SECOCHOLESTA-5,7,10(19)-TRIENE-1.ALPHA.,3.BETA.,25-TRIOL
Common Name English
FALECALCITRIOL [MART.]
Common Name English
FLOCALCITRIOL
Common Name English
HORNEL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C39713
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
Code System Code Type Description
INN
7103
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EPA CompTox
DTXSID601027560
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EVMPD
SUB07498MIG
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PUBCHEM
5282190
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DRUG CENTRAL
1127
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MESH
C040488
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ChEMBL
CHEMBL2106158
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SMS_ID
100000081532
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CAS
83805-11-2
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FDA UNII
G70A8514T8
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NCI_THESAURUS
C80884
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WIKIPEDIA
FALECALCITRIOL
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
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