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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 of DOXERCALCIFEROL

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
Molecular Formula C28H44O2
Molecular Weight 412.6478
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 3
Optical Activity UNSPECIFIED

Description
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

1999
174
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
CYP3A4 is a human microsomal vitamin D 25-hydroxylase.
2004 Apr
Functional evolution of the vitamin D and pregnane X receptors.
2007 Nov 12
Patents

Patents

07175854
29

Sample Use Guides

In Vivo Use Guide
Curator's Comment: administered at dialysis
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:05 GMT 2023
Record UNII
3DIZ9LF5Y9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXERCALCIFEROL
INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
NDF-RT N0000006337
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
NCI_THESAURUS C39713
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
NDF-RT N0000006337
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
NDF-RT N0000175907
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
NDF-RT N0000006337
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
NDF-RT N0000006337
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
EPA PESTICIDE CODE 129001
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
WHO-VATC QH05BX03
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
WHO-ATC H05BX03
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
Code System Code Type Description
DRUG CENTRAL
957
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200810
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
IUPHAR
2790
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
RS_ITEM_NUM
1225601
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
FDA UNII
3DIZ9LF5Y9
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
WIKIPEDIA
DOXERCALCIFEROL
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
CHEBI
4712
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID1034214
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
USAN
KK-96
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
SMS_ID
100000087527
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
MERCK INDEX
m4754
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY Merck Index
PUBCHEM
5281107
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
DRUG BANK
DB06410
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
RXCUI
11516
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C2645
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
EVMPD
SUB01826MIG
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
DAILYMED
3DIZ9LF5Y9
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
CAS
54573-75-0
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
INN
7878
Created by admin on Fri Dec 15 15:24:05 GMT 2023 , Edited by admin on Fri Dec 15 15:24:05 GMT 2023
PRIMARY
Related Record Type Details
Structure of 1.ALPHA.,24S-DIHYDROXYVITAMIN D2
METABOLITE ACTIVE -> PRODRUG
doxercalciferol is activated by CYP 27 in the liver to form 1.alpha.,25-(OH)2D2 (major metabolite) and 1.alpha.,24-dihydroxyvitamin D2 (minor metabolite).
MINOR
Structure of 1,25-DIHYDROXYCALCIFEROL
METABOLITE ACTIVE -> PRODRUG
doxercalciferol is activated by CYP 27 in the liver to form 1.alpha.,25-(OH)2D2 (major metabolite) and 1.alpha.,24-dihydroxyvitamin D2 (minor metabolite).
MAJOR
Related Record Type Details
Structure of (5Z,7E)-9,10-SECOERGOSTA-5,7,10(19)-TRIENE-1.ALPHA.,3.BETA.-DIOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (5Z,7E,22E)-9,10-SECOERGOSTA-5,7,10(19),22-TETRAENE-1.BETA.,3.BETA.-DIOL
IMPURITY -> PARENT
If possible from manufacturing process
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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