FALECALCITRIOL

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 Search

SMILES

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

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
Sources: http://en.pharmacodia.com/yaodu/html/v1/chemicals/92cc227532d17e56e07902b254dfad10.html
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.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Renal osteodystrophy 11 Sources: http://link.springer.com/article/10.1007/s007740050027	Primary	Preclinical	Unknown Approved Use Unknown
Secondary hyperparathyroidism 9 Sources: http://en.pharmacodia.com/yaodu/html/v1/chemicals/92cc227532d17e56e07902b254dfad10.html	Primary	Approved 8583	Hornel Approved Use Unknown Launch Date 2001
Osteomalacia 2 Sources: http://en.pharmacodia.com/yaodu/html/v1/chemicals/92cc227532d17e56e07902b254dfad10.html	Primary	Approved 8583	Hornel Approved Use Unknown Launch Date 2001
Rickets 3 Sources: http://en.pharmacodia.com/yaodu/html/v1/chemicals/92cc227532d17e56e07902b254dfad10.html	Primary	Approved 8583	Hornel Approved Use Unknown Launch Date 2001

C_max

Value	Dose	Co-administered	Analyte	Population
28 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8155746/	2 μg single, oral dose: 2 μg route of administration: Oral experiment type: SINGLE co-administered:		FALECALCITRIOL serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8155746/	2 μg single, oral dose: 2 μg route of administration: Oral experiment type: SINGLE co-administered:		FALECALCITRIOL serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.3 ug 1 times / day multiple, oral Studied dose Dose: 0.3 ug, 1 times / day Route: oral Route: multiple Dose: 0.3 ug, 1 times / day Sources: https://www.proquest.com/docview/1114466213	unhealthy Health Status: unhealthy Sex: M+F Food Status: FED Sources: https://www.proquest.com/docview/1114466213	Other AEs: Hypercalcemia, anorexia... Other AEs: Hypercalcemia (9 patients) anorexia (1 pt) Sources: https://www.proquest.com/docview/1114466213
2 ug single, oral Studied dose Dose: 2 ug Route: oral Route: single Dose: 2 ug Sources: https://pubmed.ncbi.nlm.nih.gov/8155746/	healthy Health Status: healthy Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8155746/	Sources: https://pubmed.ncbi.nlm.nih.gov/8155746/

AEs

AE	Significance	Dose	Population
anorexia	1 pt	0.3 ug 1 times / day multiple, oral Studied dose Dose: 0.3 ug, 1 times / day Route: oral Route: multiple Dose: 0.3 ug, 1 times / day Sources: https://www.proquest.com/docview/1114466213	unhealthy Health Status: unhealthy Sex: M+F Food Status: FED Sources: https://www.proquest.com/docview/1114466213
Hypercalcemia	9 patients	0.3 ug 1 times / day multiple, oral Studied dose Dose: 0.3 ug, 1 times / day Route: oral Route: multiple Dose: 0.3 ug, 1 times / day Sources: https://www.proquest.com/docview/1114466213	unhealthy Health Status: unhealthy Sex: M+F Food Status: FED Sources: https://www.proquest.com/docview/1114466213

PubMed

Title	Date	PubMed
Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3.	2000 Aug	11003160
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	16059639

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:05:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:05:39 GMT 2025`
Record UNII	G70A8514T8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FALECALCITORIOL

Preferred Name

English

FALECALCITRIOL

Official Name

English

ST630

Code

English

FALECALCITRIOL [JAN]

Common Name

English

RO 23-4194

Code

English

RO234194

Code

English

Falecalcitriol [WHO-DD]

Common Name

English

falecalcitriol [INN]

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

ST-630

Code

English

FALECALCITRIOL [MART.]

Common Name

English

FLOCALCITRIOL

Common Name

English

HORNEL

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C39713