U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H44O2
Molecular Weight 400.6381
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CALCIFEDIOL ANHYDROUS

SMILES

C=C/1CC[C@@]([H])(C\C1=C(/[H])\C(\[H])=C\2/CCC[C@]3(C)[C@]([H])(CC[C@@]23[H])[C@]([H])(C)CCCC(C)(C)O)O

InChI

InChIKey=JWUBBDSIWDLEOM-DTOXIADCSA-N
InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1

HIDE SMILES / InChI
Calcifediol (25-Hydroxyvitamin D3 or 25-hydroxycholecalciferol) is a biologically active vitamin D3 metabolite. It is concluded that the liver is the major if not the only physiologic site of hydroxylation of vitamin D3 into calcifediol. Calcifediol is a prohormone of the active form of vitamin D3, calcitriol (1,25-dihydroxyvitamin D3). Calcifediol is converted to calcitriol by cytochrome P450 27B1 (CYP27B1), also called 1-alpha hydroxylase, primarily in the kidney. Calcitriol binds to the vitamin D receptor in target tissues and activates vitamin D responsive pathways that result in increased intestinal absorption of calcium and phosphorus and reduced parathyroid hormone synthesis. RAYALDEE (calcifediol) extended-release capsules is indicated for the treatment of secondary hyperparathyroidism in adult patients with stage 3 or 4 chronic kidney disease.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RAYALDEE

Approved Use

Calcifediol indicated for the treatment of secondary hyperparathyroidism in adults with stage 3 or 4 chronic kidney disease and serum total 25-hydroxyvitamin D levels less than 30 ng/mL

Launch Date

1.46603521E12
Primary
CALDEROL

Approved Use

Unknown

Launch Date

3.34195196E11
Primary
CALDEROL

Approved Use

Unknown

Launch Date

3.34195196E11
Primary
CALDEROL

Approved Use

Unknown

Launch Date

3.34195196E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
73.2 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CALCIFEDIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1704.4 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CALCIFEDIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11 day
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CALCIFEDIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CALCIFEDIOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Other AEs: Anemia, Nasopharyngitis...
Other AEs:
Anemia (4.9%)
Nasopharyngitis (4.9%)
Blood creatinine increased (4.9%)
Dyspnea (4.2%)
Cough (3.5%)
Cardiac failure congestive (3.5%)
Constipation (3.2%)
Bronchitis (2.8%)
Hyperkalemia (2.5%)
Osteoarthritis (2.1%)
Hyperuricemia (1.8%)
Contusion (1.8%)
Pneumonia (1.4%)
Chronic obstructive pulmonary disease (1.4%)
Calcium increased serum (4.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Chronic obstructive pulmonary disease 1.4%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Pneumonia 1.4%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Contusion 1.8%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Hyperuricemia 1.8%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Osteoarthritis 2.1%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Hyperkalemia 2.5%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Bronchitis 2.8%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Constipation 3.2%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Cardiac failure congestive 3.5%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Cough 3.5%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Calcium increased serum 4.2%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Dyspnea 4.2%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Anemia 4.9%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Blood creatinine increased 4.9%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Nasopharyngitis 4.9%
30 ug 1 times / day multiple, oral (starting)
Dose: 30 ug, 1 times / day
Route: oral
Route: multiple
Dose: 30 ug, 1 times / day
Sources:
unhealthy, 66 years (range: 25-85 years)
n = 285
Health Status: unhealthy
Condition: secondary hyperparathyroidism
Age Group: 66 years (range: 25-85 years)
Sex: M+F
Population Size: 285
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Determination of vitamin D and its metabolites in plasma from normal and anephric man.
1979 Jul 15
Interrelationship of serum 25-hydroxyvitamin D3 and 1,25-dihydroxyvitamin D in juvenile renal osteodystrophy after therapy with 25-hydroxyvitamin D3.
1982
Tubular aggregates in a case of osteomalacic myopathy due to anticonvulsant drugs.
1984 Jan-Feb
Hypercalcemia in 25 OH D3 treated patients receiving a calcium exchange resin.
1985 Jun
The effect of vitamin D status on cutaneous sterologenesis in vivo and in vitro.
1987 Sep 14
Inhibition of tubercle bacilli in cultured human macrophages by chloroquine used alone and in combination with streptomycin, isoniazid, pyrazinamide, and two metabolites of vitamin D3.
1990 Nov
Vitamin D3 compounds regulate human immunodeficiency virus type 1 replication in U937 monoblastoid cells and in monocyte-derived macrophages.
1993 Feb
Proteins in the heat shock-70 family specifically bind 25-hydroxyvitamin D3 and 17beta-estradiol.
1998 Apr
Calcidiol and PTH levels in women attending an osteoporosis program.
1999 Apr
A pilot study to assess the safety and efficacy of topical calcipotriol treatment in childhood psoriasis.
1999 Jul-Aug
Kidney microsomal 25- and 1alpha-hydroxylase in vitamin D metabolism: catalytic properties, molecular cloning, cellular localization and expression during development.
2002 Feb 28
De-orphanization of cytochrome P450 2R1: a microsomal vitamin D 25-hydroxilase.
2003 Sep 26
Serum levels of prostate-specific antigen and vitamin D in peritoneal dialysis patients.
2004
Overview of general physiologic features and functions of vitamin D.
2004 Dec
Vitamin D(3) metabolism in human glioblastoma multiforme: functionality of CYP27B1 splice variants, metabolism of calcidiol, and effect of calcitriol.
2005 Aug 1
Retinoic acid via RARalpha inhibits the expression of 24-hydroxylase in human prostate stromal cells.
2005 Dec 30
Androgen enhances the antiproliferative activity of vitamin D3 by suppressing 24-hydroxylase expression in LNCaP cells.
2006 Apr
Functional evolution of the vitamin D and pregnane X receptors.
2007 Nov 12
Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile.
2010 Mar 30
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.
2011 Feb 3
Patents

Sample Use Guides

The initial dose of RAYALDEE (calcifediol) extended-release capsules is 30 mcg administered orally once daily at bedtime. Serum calcium should be below 9.8 mg/dL before initiating treatment. Monitor serum calcium, phosphorus, 25-hydroxyvitamin D and intact parathyroid hormone (PTH) 3 months after starting therapy or changing dose. Increase the dose to 60 mcg once daily after 3 months if intact PTH is above the treatment goal. Ensure serum calcium is below 9.8 mg/dL, phosphorus is below 5.5 mg/dL and 25-hydroxyvitamin D is below 100 ng/mL before increasing the dose. Suspend dosing if intact PTH is persistently abnormally low, serum calcium is consistently above the normal range or serum 25­ hydroxyvitamin D is consistently above 100 ng/mL
Route of Administration: Oral
Vitamin D metabolites down-regulated stimulated IL-8 only in those hyperinflammatory monocyte-derived macrophages, and only when used at high doses (>100 nM for Calcifediol).
Name Type Language
CALCIFEDIOL ANHYDROUS
Common Name English
CALCIDIOL
Common Name English
CALCIFEDIOL, ANHYDROUS
Common Name English
CALCIFEDIOL,ANHYDROUS
VANDF  
Common Name English
CALCIFEDIOL [MI]
Common Name English
CALCIFEDIOL [INN]
Common Name English
CALCIFEDIOL,ANHYDROUS [VANDF]
Common Name English
Classification Tree Code System Code
LOINC 83071-1
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
NDF-RT N0000175908
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
NCI_THESAURUS C39713
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
LOINC 68438-1
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
LOINC 62292-8
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
WHO-ATC A11CC06
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
LOINC 83070-3
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
Code System Code Type Description
INN
3057
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
MERCK INDEX
M2911
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00146
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
PUBCHEM
5283731
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
NCI_THESAURUS
C77155
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
EVMPD
SUB32968
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
ALTERNATIVE
EVMPD
SUB06045MIG
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
EPA CompTox
19356-17-3
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
RXCUI
1855064
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
FDA UNII
T0WXW8F54E
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
ECHA (EC/EINECS)
242-990-9
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY
CAS
19356-17-3
Created by admin on Sat Jun 26 10:01:16 UTC 2021 , Edited by admin on Sat Jun 26 10:01:16 UTC 2021
PRIMARY