Calcifediol

Identification

Summary

Calcifediol is an active metabolite of vitamin D used to treat hyperparathyroidism as well as to combat hypocalcemia in dialysis patients.

Brand Names
Rayaldee
Generic Name
Calcifediol
DrugBank Accession Number
DB00146
Background

The major circulating metabolite of vitamin D3 (cholecalciferol). It is produced in the liver and is the best indicator of the body's vitamin D stores. It is effective in the treatment of rickets and osteomalacia, both in azotemic and non-azotemic patients. Calcifediol also has mineralizing properties.

Type
Small Molecule
Groups
Approved, Nutraceutical
Structure
Weight
Average: 400.6371
Monoisotopic: 400.334130652
Chemical Formula
C27H44O2
Synonyms
  • (3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,25-diol
  • (3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol
  • (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol
  • 25-hydroxycholecalciferol
  • 25-Hydroxyvitamin D3
  • Calcidiol
  • Calcifediol
  • Calcifédiol
  • Calcifediol anhydrous
  • Calcifediolum

Pharmacology

Indication

Used to treat vitamin D deficiency or insufficiency, refractory rickets (vitamin D resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. Also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofSecondary hyperparathyroidism•••••••••••••••••••••••• • •••••••••• ••• ••••• •• •• ••••••
Treatment ofSecondary hyperparathyroidism•••••••••••••••••••••••• • •••••••••• ••• ••••• •• •• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Calcidiol is the precursor of vitamin D3. Vitamin D3 is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of vitamin A. The classical manifestations of vitamin D deficiency is rickets, which is seen in children and results in bony deformaties including bowed long bones. Deficiency in adults leads to the disease osteomalacia. Both rickets and osteomalacia reflect impaired mineralization of newly synthesized bone matrix, and usually result from a combination of inadequate exposure to sunlight and decreased dietary intake of vitamin D. Common causes of vitamin D deficiency include genetic defects in the vitamin D receptor, severe liver or kidney disease, and insufficient exposure to sunlight. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma.

Mechanism of action

Calcidiol is transformed in the kidney by 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to calcitriol, the active form of vitamin D3. Calcitriol binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.

TargetActionsOrganism
AVitamin D3 receptor
agonist
Humans
Absorption

Readily absorbed.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Calcidiol undergoes hydroxylation in the mitochondria of kidney tissue, and this reaction is activated by the renal 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to produce calcitriol (1,25- dihydroxycholecalciferol), the active form of vitamin D3.

Route of elimination

Not Available

Half-life

288 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Bone pain, constipation (especially in children or adolescents), diarrhea, drowsiness, dryness of mouth; headache (continuing), increased thirst, increase in frequency of urination, especially at night, or in amount of urine, irregular heartbeat, itching skin, loss of appetite, metallic taste, muscle pain, nausea or vomiting (especially in children or adolescents), unusual tiredness or weakness.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetyldigitoxinThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Calcifediol is combined with Acetyldigitoxin.
AlfacalcidolThe risk or severity of adverse effects can be increased when Calcifediol is combined with Alfacalcidol.
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Calcifediol.
Beclomethasone dipropionateThe therapeutic efficacy of Calcifediol can be decreased when used in combination with Beclomethasone dipropionate.
BendroflumethiazideThe risk or severity of hypercalcemia can be increased when Bendroflumethiazide is combined with Calcifediol.
Food Interactions
  • Take with or without food. A high-fat, high-calorie meal may increase the AUC and Cmax of calcifediol by up to 3.5 and 5 fold, respectively.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Calcifediol hydrateP6YZ13C99Q63283-36-3WRLFSJXJGJBFJQ-WPUCQFJDSA-N
International/Other Brands
Calderol (Upjohn) / Caldiol (Medica) / De Kai (China Otsuka) / Dedrogyl (Desma) / Dédrogyl (DB) / Didrogyl (Bruno Farm.) / Hidroferol (Faes)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RayaldeeCapsule, extended release30 ug/1OralOpko Pharmaceuticals Llc2016-10-25Not applicableUS flag
RayaldeeCapsule30 mcgOralEIRGEN PHARMA LIMITEDNot applicableNot applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
HEPASELAMİN AMİNOASİT IV İNFÜZYON ÇÖZELTİSİ 500 ML SETLİ ŞİŞECalcifediol (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2003-12-31Not applicableTurkey flag
HEPASELAMİN AMİNOASİT IV İNFÜZYON ÇÖZELTİSİ 500 ML SETSİZ ŞİŞECalcifediol (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2003-12-31Not applicableTurkey flag
HEPATAMINE %8 500 ML(SETLI)Calcifediol (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Sodium bisulfite (0.01 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.1990-01-162024-01-23Turkey flag
HEPATAMINE %8 500 ML(SETSIZ)Calcifediol (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Sodium bisulfite (0.01 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.1990-01-162024-01-23Turkey flag

Categories

ATC Codes
A11CC06 — CalcifediolH05BX05 — Calcifediol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Vitamin D and derivatives
Direct Parent
Vitamin D and derivatives
Alternative Parents
Triterpenoids / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Tertiary alcohol / Triterpenoid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
diol, D3 vitamins, hydroxycalciol (CHEBI:17933) / Vitamin D3 and derivatives (C01561) / Vitamin D3 and derivatives (LMST03020246)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
T0WXW8F54E
CAS number
19356-17-3
InChI Key
JWUBBDSIWDLEOM-DTOXIADCSA-N
InChI
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
IUPAC Name
(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
SMILES
C[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C

References

Synthesis Reference

Dae-Jung Kang, Jong-Hyuk Im, Hyun-Jung Jung, Jae-Hoon Kang, "BUFFER COMPOSITION FOR CATALYZING THE PREPARATION OF CALCITRIOL OR CALCIFEDIOL AND METHOD FOR PREPARING CALCITRIOL OR CALCIFEDIOL USING SAME." U.S. Patent US20120064584, issued March 15, 2012.

US20120064584
General References
  1. FDA Approved Drug Products: RAYALDEE (calcifediol) extended-release capsules [Link]
Human Metabolome Database
HMDB0003550
KEGG Compound
C01561
PubChem Compound
5283731
PubChem Substance
46505690
ChemSpider
4446820
BindingDB
50521013
RxNav
1855064
ChEBI
17933
ChEMBL
CHEMBL1040
ZINC
ZINC000004474414
Therapeutic Targets Database
DAP000290
PharmGKB
PA164745614
PDBe Ligand
VDY
PDRhealth
PDRhealth Drug Page
Wikipedia
Calcifediol
PDB Entries
1j78 / 1mz9 / 3a51 / 5ien / 5ieo / 5iep

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Organon usa inc
Packagers
  • Organon Pharmaceuticals
Dosage Forms
FormRouteStrength
Solution / dropsOral0.15 MG/ML
SolutionIntravenous
CapsuleOral266 Mikrogramm
Capsule, liquid filledOral0.266 mg
Solution / dropsOral0266 MG/0.5ML
CapsuleOral0.266 MG
CapsuleOral
CapsuleOral30 mcg
CapsuleOral30 MICROGRAMMI
Capsule, extended releaseOral30 ug/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8906410No2014-12-092027-02-02US flag
US6582727No2003-06-242020-08-22US flag
US8361488No2013-01-292028-07-19US flag
US9408858No2016-08-092028-04-25US flag
US9498486No2016-11-222028-04-25US flag
US8778373No2014-07-152028-04-25US flag
US8426391No2013-04-232028-08-27US flag
US8207149No2012-06-262028-04-25US flag
US9861644No2018-01-092034-03-14US flag
US9943530No2018-04-172027-02-02US flag
US9925147No2018-03-272028-04-25US flag
US10213442No2019-02-262027-02-02US flag
US10300078No2019-05-282034-03-14US flag
US10357502No2019-07-232034-03-14US flag
US11154509No2021-10-262028-04-25US flag
US11253528No2014-03-142034-03-14US flag
US11801253No2010-09-072030-09-07US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0022 mg/mLALOGPS
logP6.71ALOGPS
logP5.65Chemaxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.38Chemaxon
pKa (Strongest Basic)-0.98Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity125.06 m3·mol-1Chemaxon
Polarizability50.38 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9953
Blood Brain Barrier+0.9164
Caco-2 permeable+0.8891
P-glycoprotein substrateSubstrate0.7454
P-glycoprotein inhibitor IInhibitor0.5209
P-glycoprotein inhibitor IIInhibitor0.6087
Renal organic cation transporterNon-inhibitor0.7849
CYP450 2C9 substrateNon-substrate0.8379
CYP450 2D6 substrateNon-substrate0.9004
CYP450 3A4 substrateSubstrate0.7815
CYP450 1A2 substrateNon-inhibitor0.8874
CYP450 2C9 inhibitorNon-inhibitor0.9229
CYP450 2D6 inhibitorNon-inhibitor0.9488
CYP450 2C19 inhibitorNon-inhibitor0.7885
CYP450 3A4 inhibitorNon-inhibitor0.7968
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.56
Ames testNon AMES toxic0.8612
CarcinogenicityNon-carcinogens0.917
BiodegradationNot ready biodegradable0.991
Rat acute toxicity4.1429 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8189
hERG inhibition (predictor II)Non-inhibitor0.7589
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001i-2900000000-33a8e563016d6e2e358e
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00lr-2900000000-f6bedf68127696063061
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ab9-3029000000-4c75b5cfbc422ba2a344
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-2900000000-33a8e563016d6e2e358e
GC-MS Spectrum - GC-MSGC-MSsplash10-00lr-2900000000-f6bedf68127696063061
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0429000000-9dce6941135d59ce689e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-48dea4e664e4a8acba97
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k9l-6629100000-14057d65e22bad86a309
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1009000000-839439794efc312e2f80
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-0319000000-7e5153314aba3197550d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0avi-2953000000-3840a04b70d21851010f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-217.3865044
predicted
DarkChem Lite v0.1.0
[M-H]-194.9139647
predicted
DarkChem Standard v0.1.0
[M-H]-207.6283044
predicted
DarkChem Lite v0.1.0
[M-H]-218.6883044
predicted
DarkChem Lite v0.1.0
[M-H]-202.94073
predicted
DeepCCS 1.0 (2019)
[M+H]+216.4439044
predicted
DarkChem Lite v0.1.0
[M+H]+202.7943044
predicted
DarkChem Lite v0.1.0
[M+H]+206.0010044
predicted
DarkChem Lite v0.1.0
[M+H]+218.5856044
predicted
DarkChem Lite v0.1.0
[M+H]+204.76723
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.1276044
predicted
DarkChem Lite v0.1.0
[M+Na]+203.3194044
predicted
DarkChem Lite v0.1.0
[M+Na]+206.0874044
predicted
DarkChem Lite v0.1.0
[M+Na]+217.2326044
predicted
DarkChem Lite v0.1.0
[M+Na]+210.37303
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 Da
References
  1. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Iron ion binding
Specific Function
Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
Gene Name
CYP27B1
Uniprot ID
O15528
Uniprot Name
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial
Molecular Weight
56503.475 Da
References
  1. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99. doi: 10.1016/j.bbapap.2010.06.022. Epub 2010 Jul 7. [Article]
  2. Bernad M, Jaramillo G, Aguado P, del Campo T, Coya J, Martin Mola E, Gijon Banos J, Saldana Barrera H, Martinez ME: [Polymorphism of the gene of vitamin D receptor and bone mineral density in postmenopausal women]. Med Clin (Barc). 1999 May 15;112(17):651-5. [Article]
  3. Diesel B, Radermacher J, Bureik M, Bernhardt R, Seifert M, Reichrath J, Fischer U, Meese E: Vitamin D(3) metabolism in human glioblastoma multiforme: functionality of CYP27B1 splice variants, metabolism of calcidiol, and effect of calcitriol. Clin Cancer Res. 2005 Aug 1;11(15):5370-80. [Article]
  4. Eto TA, Nakamura Y, Taniguchi T, Miyamoto K, Nagatomo J, Maeda Y, Higashi S, Okuda K, Setoguchi T: Assay of 25-hydroxyvitamin D3 1 alpha-hydroxylase in rat kidney mitochondria. Anal Biochem. 1998 Apr 10;258(1):53-8. [Article]
  5. Hart GR, Furniss JL, Laurie D, Durham SK: Measurement of vitamin D status: background, clinical use, and methodologies. Clin Lab. 2006;52(7-8):335-43. [Article]
  6. Vigo Gago E, Cadarso-Suarez C, Perez-Fernandez R, Romero Burgos R, Devesa Mugica J, Segura Iglesias C: Association between vitamin D receptor FokI. Polymorphism and serum parathyroid hormone level in patients with chronic renal failure. J Endocrinol Invest. 2005 Feb;28(2):117-21. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity
Specific Function
Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can...
Gene Name
CYP24A1
Uniprot ID
Q07973
Uniprot Name
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
Molecular Weight
58874.695 Da
References
  1. Wjst M, Altmuller J, Faus-Kessler T, Braig C, Bahnweg M, Andre E: Asthma families show transmission disequilibrium of gene variants in the vitamin D metabolism and signalling pathway. Respir Res. 2006 Apr 6;7:60. doi: 10.1186/1465-9921-7-60. [Article]
  2. CYP24A1 gene - Genetics Home Reference - NIH [Link]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42