Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H44O2 |
Molecular Weight | 400.6371 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/4310770
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4310770
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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4300699
Curator's Comment: 1968
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19944755 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | RAYALDEE Approved UseCalcifediol 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 Date2016 |
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Primary | CALDEROL Approved UseUnknown Launch Date1980 |
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Primary | CALDEROL Approved UseUnknown Launch Date1980 |
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Primary | CALDEROL Approved UseUnknown Launch Date1980 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
73.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24516879/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1704.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24516879/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24516879/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24516879/ |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Vitamin D3 compounds regulate human immunodeficiency virus type 1 replication in U937 monoblastoid cells and in monocyte-derived macrophages. | 1993 Feb |
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Calcidiol and PTH levels in women attending an osteoporosis program. | 1999 Apr |
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A pilot study to assess the safety and efficacy of topical calcipotriol treatment in childhood psoriasis. | 1999 Jul-Aug |
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Kidney microsomal 25- and 1alpha-hydroxylase in vitamin D metabolism: catalytic properties, molecular cloning, cellular localization and expression during development. | 2002 Feb 28 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26178144
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
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83071-1
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C39713
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68438-1
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62292-8
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A11CC06
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83070-3
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Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS |
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LABELED -> NON-LABELED |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
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