DOXERCALCIFEROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H44O2
Molecular Weight	412.6478
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

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)\C=C\[C@H](C)C(C)C

InChI

InChIKey=HKXBNHCUPKIYDM-CGMHZMFXSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB06410
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020862s030lbl.pdf

Doxercalciferol is a synthetic vitamin D2 analog 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. Doxercalciferol is indicated for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis, as well as for the treatment of secondary hyperparathyroidism in patients with Stage 3 or Stage 4 chronic kidney disease. Doxercalciferol is marketed under the brand name Hectorol by Genzyme Corporation, and is manufactured by Catalent Pharma Solutions, Inc.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin D receptor 25 Target ID: CHEMBL1977 Sources: http://www.drugbank.ca/drugs/DB06410	Agonist 2678
Sterol 26-hydroxylase, mitochondrial 1 Target ID: CHEMBL5992 Sources: http://www.drugbank.ca/drugs/DB06410	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Secondary hyperparathyroidism in patients with chronic kidney disease on dialysis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020862s030lbl.pdf	Primary		Approved 8429	HECTOROL Approved Use Dialysis Patients: Hectorol is indicated for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis. Pre-Dialysis Patients: Hectorol is indicated for the treatment of secondary hyperparathyroidism in patients with Stage 3 or Stage 4 chronic kidney disease. Launch Date 1999

C_max

Value	Dose	Co-administered	Analyte	Population
29.9 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12637645	5 μg 1 times / 2 days multiple, oral dose: 5 μg route of administration: Oral experiment type: MULTIPLE co-administered:		DOXERCALCIFEROL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
957 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12637645	5 μg 1 times / 2 days multiple, oral dose: 5 μg route of administration: Oral experiment type: MULTIPLE co-administered:		DOXERCALCIFEROL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
34 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12637645	5 μg 1 times / 2 days multiple, oral dose: 5 μg route of administration: Oral experiment type: MULTIPLE co-administered:		DOXERCALCIFEROL serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4712	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4712
ChemicalBook	CB8394169	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8394169
MolPort	MolPort-018-493-676	https://www.molport.com/shop/molecule-link/MolPort-018-493-676
ZINC	ZINC000004641374	http://zinc15.docking.org/substances/ZINC000004641374

PubMed

Title	Date	PubMed
		252160414
CYP3A4 is a human microsomal vitamin D 25-hydroxylase.	2004 Apr	15005856
Effectiveness of vitamin D analogues in treating large tumors and during prolonged use in murine retinoblastoma models.	2004 Sep	15364716
The vitamin D prodrugs 1alpha(OH)D2, 1alpha(OH)D3 and BCI-210 suppress PTH secretion by bovine parathyroid cells.	2006 Mar	16221703
Functional evolution of the vitamin D and pregnane X receptors.	2007 Nov 12	17997857

Patents

Sample Use Guides

In Vivo Use Guide

Dialysis: The recommended initial dose of Hectorol is 10 mcg administered three times weekly at dialysis (approximately every other day). The initial dose should be adjusted, as needed, in order to lower blood iPTH into the range of 150 to 300 pg/mL.

Route of Administration: Intravenous

In Vitro Use Guide

Doxercalciferol significantly suppressed PTH secretion or reduced PTH mRNA level at 10(-8), 10(-10), and 10(-11)M in bovine parathyroid cells

Name

Type

Language

DOXERCALCIFEROL

Official Name

English

doxercalciferol [INN]

Common Name

English

9,10-SECOERGOSTA-5,7,10(19),22-TETRAENE-1,3-DIOL, (1.ALPHA.,3.BETA.,5Z,7E,22E)-

Common Name

English

HECTOROL

Brand Name

English

TSA-840

Code

English

DOXERCALCIFEROL [USAN]

Common Name

English

(5Z,7E,22E)-9,10-SECOERGOSTA-5,7,10(19),22-TETRAENE-1.ALPHA.,3.BETA.-DIOL

Common Name

English

1-ALPHA-HYDROXYERGOCALCIFEROL

Common Name

English

1α-Hydroxyergocalciferol

Common Name

English

DOXERCALCIFEROL [MI]

Common Name

English

DOXERCALCIFEROL [USP-RS]

Common Name

English

GZ427397

Code

English

Doxercalciferol [WHO-DD]

Common Name

English

1-HYDROXYERGOCALCIFEROL

Common Name

English

DOXERCALCIFEROL [VANDF]

Common Name

English

1-.ALPHA.-HYDROXYERGOCALCIFEROL

Common Name

English

DOXERCALCIFEROL [USP MONOGRAPH]

Common Name

English

1.ALPHA.-HYDROXYVITAMIN D2

Common Name

English

DOXERCALCIFEROL [ORANGE BOOK]

Common Name

English

1,3-CYCLOHEXANEDIOL, 4-METHYLENE-5-((2E)-2-((1R,3AS,7AR)-OCTAHYDRO-7A-METHYL-1-((1R,2E)-1,4,5-TRIMETHYL-2-HEXEN-1-YL)-4H-INDEN-4-YLIDENE)ETHYLIDENE)-, (1R,3S,5Z)-

Common Name

English

DOXERCALCIFEROL [MART.]

Common Name

English

Classification Tree Code System Code

LIVERTOX

327