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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H44O2.H2O
Molecular Weight 418.6523
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CALCIFEDIOL

SMILES

O.[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C)[C@H](C)CCCC(C)(C)O

InChI

InChIKey=WRLFSJXJGJBFJQ-WPUCQFJDSA-N
InChI=1S/C27H44O2.H2O/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;1H2/b21-11+,22-12-;/t20-,23+,24-,25+,27-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C27H44O2
Molecular Weight 400.6371
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Tubular aggregates in a case of osteomalacic myopathy due to anticonvulsant drugs.
1984 Jan-Feb
1 alpha,25-dihydroxyvitamin D3 inhibits productive infection of human monocytes by HIV-1.
1991 Apr 30
Vitamin D3 compounds regulate human immunodeficiency virus type 1 replication in U937 monoblastoid cells and in monocyte-derived macrophages.
1993 Feb
Calcidiol and PTH levels in women attending an osteoporosis program.
1999 Apr
Kidney microsomal 25- and 1alpha-hydroxylase in vitamin D metabolism: catalytic properties, molecular cloning, cellular localization and expression during development.
2002 Feb 28
Androgen enhances the antiproliferative activity of vitamin D3 by suppressing 24-hydroxylase expression in LNCaP cells.
2006 Apr
Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D.
2006 Jul-Aug
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:03:42 UTC 2023
Edited
by admin
on Fri Dec 15 16:03:42 UTC 2023
Record UNII
P6YZ13C99Q
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
CALCIFEDIOL
EP   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
CALCIFEDIOL [VANDF]
Common Name English
U-32070E
Code English
HIDROFEROL
Brand Name English
DIDROGYL
Brand Name English
CALCIFEDIOL [EP IMPURITY]
Common Name English
CALCIFEDIOL [ORANGE BOOK]
Common Name English
CALCIFEDIOL HYDRATE
Common Name English
CALCIFEDIOL [USAN]
Common Name English
U-32,070E
Code English
9,10-Secocholesta-5,7,10(19)-triene-3,25-diol, monohydrate, (3β,5Z,7E)-
Systematic Name English
25-Hydroxycholecalciferol monohydrate
Common Name English
1H-Indene-1-pentanol, 4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-α,α,ε,7a-tetramethyl-, hydrate (1:1), (εR,1R,3aS,4E,7aR)-
Systematic Name English
CALCIFEDIOL [USP-RS]
Common Name English
Calcifediol monohydrate [WHO-DD]
Common Name English
CALDEROL
Brand Name English
CALCIFEDIOL [USP MONOGRAPH]
Common Name English
Calcifediol [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 138
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
NCI_THESAURUS C39713
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
WHO-ATC A11CC06
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
WHO-VATC QA11CC06
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
Code System Code Type Description
FDA UNII
P6YZ13C99Q
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
DRUG BANK
DBSALT002443
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
DAILYMED
P6YZ13C99Q
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
PUBCHEM
6441383
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
SMS_ID
300000038170
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
RXCUI
1889
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1040
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
DRUG CENTRAL
464
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
WIKIPEDIA
CALCIFEDIOL
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
CAS
63283-36-3
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
NCI_THESAURUS
C65278
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
CHEBI
17933
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
MESH
D002112
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
RS_ITEM_NUM
1086108
Created by admin on Fri Dec 15 16:03:43 UTC 2023 , Edited by admin on Fri Dec 15 16:03:43 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
TARGET -> AGONIST
SUB_CONCEPT->SUBSTANCE
PARENT -> SALT/SOLVATE
BINDER->LIGAND
BINDING
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC