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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

Molecular Formula C27H38F6O3
Molecular Weight 524.5792
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 2
Optical Activity UNSPECIFIED

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%
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:29 GMT 2023
Record UNII
G70A8514T8
Record Status Validated (UNII)
Record Version
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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
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID601027560
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
EVMPD
SUB07498MIG
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
PUBCHEM
5282190
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
DRUG CENTRAL
1127
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
MESH
C040488
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106158
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
SMS_ID
100000081532
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
CAS
83805-11-2
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
FDA UNII
G70A8514T8
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
NCI_THESAURUS
C80884
Created by admin on Fri Dec 15 15:41:29 GMT 2023 , Edited by admin on Fri Dec 15 15:41:29 GMT 2023
PRIMARY
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
PRIMARY
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