NAV

Calcitriol

Identification

Summary

Calcitriol is an active metabolite of vitamin D that is used to treat hyperparathyroidism and is also used in dialysis patients to combat hypocalcemia.

Brand Names
Rocaltrol, Vectical
Generic Name
Calcitriol
DrugBank Accession Number
DB00136
Background

Calcitriol is an active metabolite of vitamin D with 3 hydroxyl (OH) groups and is commonly referred to as 1,25-dihydroxycholecalciferol, or 1alpha,25-dihydroxyvitamin D3, 1,25-dihydroxyvitamin D3. It is produced in the body after series of conversion steps of 7-dehydrocholesterol from exposure to UV light. 7-dehydrocholesterol is converted to Vitamin D3 (vitamin D3) in the skin, which is then converted to Calcifediol in the liver and kidneys. Calcifediol undergoes hydroxylation to form calcitriol via 1α-hydroxylase (CYP27B1) activity 4. Calcitriol is considered to be the most potent metabolite of vitamin D in humans 1. Renal production of calcitriol is stimulated in response to PTH, low calcium and low phosphate 4. Calcitriol plays a role in plasma calcium regulation in concert with parathyroid hormone (PTH) by enhancing absorption of dietary calcium and phosphate from the gastrointestinal tract, promoting renal tubular reabsorption of calcium in the kidneys, and stimulating the release of calcium stores from the skeletal system. In addition to promoting fatty acid synthesis and inhibiting lipolysis, calcitriol has been demonstrated to increase energy efficiency by suppressing UCP2 expression, which is modulated by signaling pathways of classical nuclear receptors (nVDR), where calcitriol acts as a natural ligand 3. There is also evidence that calcitriol modulates the action of cytokines and may regulate immune and inflammatory response, cell turnover, cell differentiation 4.

Administered orally and intravenously, calcitriol is commonly used as a medication in the treatment of secondary hyperparathyroidism and resultant metabolic bone disease, hypocalcemia in patients undergoing chronic renal dialysis, and osteoporosis. It is also available in topical form for the treatment of mild to moderate plaque psoriasis in adults. Calcitriol is marketed under various trade names including Rocaltrol (Roche), Calcijex (Abbott) and Decostriol (Mibe, Jesalis).

Type
Small Molecule
Groups
Approved, Nutraceutical
Structure
3D
Similar Structures
Weight
Average: 416.6365
Monoisotopic: 416.329045274
Chemical Formula
C27H44O3
Synonyms
  • (1S,3R,5Z,7E)-9,10-secocholesta-5,7,10-triene-1,3,25-triol
  • (1α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
  • (5Z,7E)-(1S,3R)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
  • 1-alpha-25-Dihydroxyvitamin D3
  • 1,25-DHCC
  • 1,25-dihydroxycholecalciferol
  • 1α,25-dihydroxycholecalciferol
  • 1α,25-dihydroxyvitamin D3
  • 1α,25(OH)2D3
  • Calcitriol
  • Calcitriolum
External IDs
  • DN-101
  • RO 21-5535
  • RO-21-5535
  • RO-215535
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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
Management ofHypocalcemia•••••••••••••••••••
Management ofHypocalcemia•••••••••••••••••••••• •••••••••• ••••••••
Management ofMild to moderate plaque psoriasis••••••••••••
Management ofOsteodystrophy•••••••••••••••••••
Management ofSecondary hyperparathyroidism•••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Calcitriol is a biologically active calcitrophic hormone with anti-osteoporotic, immunomodulatory, anticarcinogenic, antipsoriatic, antioxidant, and mood-modulatory activities. Its main sites of action are the intestine, bone, kidney and parathyroid hormone Label. Calcitriol is a ligand for the vitamin D nuclear receptor, which is expressed in, but not limited to, gastrointestinal (GI) tissues, bones, and kidneys 1. As an active form of vitamin D3, calcitriol elevates the plasma levels of calcium by stimulating intestinal calcium uptake, increasing reabsorption of calcium by the kidneys, and possibly increasing the release of calcium from skeletal stores. The duration of pharmacologic activity of a single dose of exogenous calcitriol is expected to be about 3 to 5 days Label.

In addition to its important role in calcium metabolism, other pharmacological effects of calcitriol have been studied in various conditions including cancer models. Various studies demonstrated expression of vitamin D receptors in cancer cell lines, including mouse myeloid leukemia cells 1. Calcitriol has been found to induce differentiation and/or inhibit cell proliferation in vitro and in vivo in many cell types, such as malignant cell lines carcinomas of the breast, prostate, colon, skin, and brain, myeloid leukemia cells, and others 2. In early human prostate cancer trials, administration of 1.5 µg/d calcitriol in male participants resulted in a reduction in the rate of PSA rise in most participants, however it was coincided with dose-limiting hypercalcemia in most participants 1. Hypercalcemia and hypercalcuria were evident in numerous initial trials, and this may be due to these trials not testing the drug at concentrations that are active in preclinical systems 2. Findings from preclinical data show an additive or synergistic antineoplastic action of calcitriol when combined with agents including dexamethasone, retinoids, and radiation, as well as several cytotoxic chemotherapy drugs such as platinum compounds 2.

Vitamin D deficiency has long been suspected to increase the susceptibility to tuberculosis. The active form of calcitriol, 1,25-(OH)2-D3, has been found to enhance the ability of mononuclear phagocytes to suppress the intracellular growth of Mycobacterium tuberculosis. 1,25-(OH)2-D3 has demonstrated beneficial effects in animal models of such autoimmune diseases as rheumatoid arthritis. Vitamin D appears to demonstrate both immune-enhancing and immunosuppressive effects.

Mechanism of action

The mechanism of action of calcitriol in the treatment of psoriasis is accounted for by their antiproliferative activity for keratinocytes and their stimulation of epidermal cell differentiation. The anticarcinogenic activity of the active form of Calcitriol appears to be correlated with cellular vitamin D receptor (VDR) levels. Vitamin D receptors belong to the superfamily of steroid-hormone zinc-finger receptors. VDRs selectively bind 1,25-(OH)2-D3 and retinoic acid X receptor (RXR) to form a heterodimeric complex that interacts with specific DNA sequences known as vitamin D-responsive elements. VDRs are ligand-activated transcription factors. The receptors activate or repress the transcription of target genes upon binding their respective ligands. It is thought that the anticarcinogenic effect of Calcitriol is mediated via VDRs in cancer cells. The immunomodulatory activity of calcitriol is thought to be mediated by vitamin D receptors (VDRs) which are expressed constitutively in monocytes but induced upon activation of T and B lymphocytes. 1,25-(OH)2-D3 has also been found to enhance the activity of some vitamin D-receptor positive immune cells and to enhance the sensitivity of certain target cells to various cytokines secreted by immune cells.

A study suggests that calcitriol plays an immunoregulatry role by suppressing the aryl hydrocarbon receptor (AhR) expression in human Th9, a pro-inflammatory CD4 T cell subset 9. This suppression subsequently leads to repressed expression of BATF, a transcription factor essential for Th9 9. Calcitriol has also been found to induce monocyte differentiation and to inhibit lymphocyte proliferation and production of cytokines, including interleukin IL-1 and IL-2, as well as to suppress immunoglobulin secretion by B lymphocytes.

TargetActionsOrganism
AVitamin D3 receptor
agonist
Humans
UHomeobox protein Hox-A10Not AvailableHumans
Absorption

Upon administration, calcitriol is rapidly absorbed from the intestines. When a single oral dose of 0.5 mcg of calcitriol was administered, the mean serum concentrations of calcitriol rose from a baseline value of 40.0±4.4 (SD) pg/mL to 60.0±4.4 pg/mL at 2 hours, and declined to 53.0±6.9 at 4 hours, 50±7.0 at 8 hours, 44±4.6 at 12 hours and 41.5±5.1 at 24 hours Label. Following administration of single doses of 0.25 to 1.0 mcg of calcitriol, the peak plasma concentrations were reached within 3 to 6 hours Label. In a pharmacokinetic study, the oral bioavailability was 70.6±5.8% in healthy male volunteers and 72.2±4.8% in male patients with uraemia 8.

Volume of distribution

Upon intravenous administration, the volume of distribution of calcitriol was 0.49±0.14 L/kg in healthy male volunteers and 0.27±0.06 l/kg in uraemic male patients participating in a pharmacokinetic study 8. There is some evidence that calcitriol is transferred into human milk at low levels (ie, 2.2±0.1 pg/mL) in mothers Label. Calcitriol from maternal circulation may also enter the fetal circulation Label.

Protein binding

Calcitriol is approximately 99.9% bound in blood, mostly by an alpha-globulin vitamin D binding protein Label.

Metabolism

Metabolism of calcitriol involves two pathways Label. The first pathway involves 24-hydroxylase activity in the kidney; this enzyme is also present in many target tissues which possess the vitamin D receptor such as the intestine. The end product of this pathway is a side chain shortened metabolite, calcitroic acid. The second pathway involves the conversion of calcitriol via the stepwise hydroxylation of carbon-26 and carbon-23, and cyclization to yield ultimately 1a,25R(OH)2-26,23S-lactone D3, which appears to be the major metabolite circulating in humans.

Ohter identified metabolites of calcitriol include 1α, 25(OH)2-24-oxo-D3; 1α, 23,25(OH)3-24-oxo-D3; 1α, 24R,25(OH)3D3; 1α, 25S,26(OH)3D3; 1α, 25(OH)2-23-oxo-D3; 1α, 25R,26(OH)3-23-oxo-D3 and 1α, (OH)24,25,26,27-tetranor-COOH-D3 Label.

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Route of elimination

In normal subjects, approximately 27% and 7% of the radioactivity appeared in the feces and urine, respectively, within 24 hours Label. Calcitriol undergoes enterohepatic recycling and biliary excretion. The metabolites of calcitriol are excreted primarily in feces. Cumulative excretion of radioactivity on the sixth day following intravenous administration of radiolabeled calcitriol averaged 16% in urine and 49% in feces Label.

Half-life

After administration of single oral doses, the elimination half life was 5-8 hours Label.

Clearance

The metabolic clearance rate was 23.5±4.34 ml/min in healthy male volunteers and 10.1±1.35 ml/min in male patients with uraemia 8. In the pediatric patients undergoing peritoneal dialysis receiving dose of 10.2 ng/kg (SD 5.5 ng/kg) for 2 months, the clearance rate was 15.3 mL/hr/kg Label.

Adverse Effects
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Toxicity

LD50 (oral, rat) = 620 μg/kg; LD50 (intraperitoneal, rat) > 5 mg/kg MSDS.

Symptoms of calcitriol toxicity mirrors the early and late signs and symptoms of vitamin D intoxication associated with hypercalcemia 10. Early signs include weakness, headache, somnolence, nausea, vomiting, dry mouth, constipation, muscle pain, bone pain and metallic taste. Late signs are characterized by polyuria, polydipsia, anorexia, weight loss, nocturia, conjunctivitis (calcific), pancreatitis, photophobia, rhinorrhea, pruritus, hyperthermia, decreased libido, elevated BUN, albuminuria, hypercholesterolemia, elevated SGOT and SGPT, ectopic calcification, hypertension, cardiac arrhythmias and, rarely, overt psychosis 10.

Pathways
Not Available
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Interactions

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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
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AbametapirThe serum concentration of Calcitriol can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Calcitriol.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Calcitriol.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Calcitriol.
AcetyldigitoxinThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Calcitriol is combined with Acetyldigitoxin.
Food Interactions
No interactions found.

Products

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Product Images
International/Other Brands
Asentar (Novacea) / Calcitriol Oral Solution (Roxane) / Decostriol (Mibe Jena (Germany), Jesalis (Hong Kong, Thailand))
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CalcijexInjection, solution1 ug/1mLIntravenousAbbvie2010-06-012012-08-01US flag
CalcijexSolution2 mcg / mLIntravenousAbbvie1990-12-312017-01-13Canada flag
CalcijexSolution1 mcg / mLIntravenousAbbvie1990-12-312017-01-13Canada flag
CalcitriolSolution1 ug/1mLIntravenousNEPHRX, LLC2009-01-27Not applicableUS flag
CalcitriolInjection, solution2 ug/1mLIntravenousAMERICAN REGENT, INC.2007-01-012007-01-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CalcitriolCapsule0.5 ug/1OralStrides Pharma Science Limited2016-12-27Not applicableUS flag
CalcitriolCapsule0.25 ug/1Oralbryant ranch prepack2014-12-122018-11-30US flag
CalcitriolCapsule, liquid filled0.50 ug/1OralBionpharma Inc.2018-06-12Not applicableUS flag
CalcitriolCapsule0.25 ug/1OralAphena Pharma Solutions Tennessee, Inc.2009-08-26Not applicableUS flag
CalcitriolCapsule, liquid filled0.25 ug/1Oralbryant ranch prepack2013-05-292019-05-31US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BONKY SOFT CAPSULECapsuleOralBIO-PHARMACEUTICALS SDN. BHD.2020-09-08Not applicableMalaysia flag
Decostriol 0.25 mcg capsuleCapsuleOralIDAMAN PHARMA SDN. BHD.2020-09-08Not applicableMalaysia flag
Osteocap CapsuleCapsuleOralMEGA LIFESCIENCES SDN. BHD.2020-09-08Not applicableMalaysia flag
RO-CAL 0.25mcgCapsuleOralPAHANG PHARMACY SDN. BHD.2020-09-08Not applicableMalaysia flag
ROCALTROL CAPSULE 0.25MCGCapsule0.25 MCGOralDKSH MALAYSIA SDN BHD2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ยาเม็ด แมกซ์มาร์วิลCalcitriol (0.5 mcg) + Alendronic acid (5 mg)Tablet, delayed releaseOralบริษัท สหแพทย์เภสัช จำกัด2015-05-182020-08-24Thailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CALDEROL 1 MCG/ML I.V. ENJEKSIYONLUK COZELTI ICEREN 2AMPUL, 5 ADETCalcitriol (1 mcg/ml)Injection, solutionIntravenousPHARMADA İLAÇ SAN. VE TİC. A.Ş.2020-03-172024-01-23Turkey flag
CALDEROL 2 MCG/ML I.V. ENJEKSIYONLUK COZELTI ICEREN 2AMPUL, 5 ADETCalcitriol (2 mcg/ml)Injection, solutionIntravenousPHARMADA İLAÇ SAN. VE TİC. A.Ş.2019-11-262024-01-23Turkey flag
ValidermCalcitriol (0.2 mg/0.2mg) + Fluticasone propionate (0.05 g/0.05g) + Tacrolimus hydrate (0.05 g/0.05g)KitTopicalAccumix Pharmaceuticals2014-12-152015-07-17US flag

Categories

ATC Codes
D05AX03 — CalcitriolA11CC04 — Calcitriol
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
triol, D3 vitamins, hydroxycalciol (CHEBI:17823) / Steroid hormones (C01673) / Vitamin D3 and derivatives (LMST03020258)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
FXC9231JVH
CAS number
32222-06-3
InChI Key
GMRQFYUYWCNGIN-NKMMMXOESA-N
InChI
InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
IUPAC Name
(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
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)C[C@H](O)C1=C

References

Synthesis Reference

Raymond E. Conrow, "Process for preparation of calcitriol lactone and related intermediates." U.S. Patent US5457245, issued April, 1994.

US5457245
General References
  1. Brawer MK: Recent Progress in the Treatment of Advanced Prostate Cancer With Intermittent Dose-Intense Calcitriol (DN-101). Rev Urol. 2007 Winter;9(1):1-8. [Article]
  2. Beer TM, Javle M, Lam GN, Henner WD, Wong A, Trump DL: Pharmacokinetics and tolerability of a single dose of DN-101, a new formulation of calcitriol, in patients with cancer. Clin Cancer Res. 2005 Nov 1;11(21):7794-9. [Article]
  3. Zemel MB, Sun X: Calcitriol and energy metabolism. Nutr Rev. 2008 Oct;66(10 Suppl 2):S139-46. doi: 10.1111/j.1753-4887.2008.00099.x. [Article]
  4. Rodriguez M, Munoz-Castaneda JR, Almaden Y: Therapeutic use of calcitriol. Curr Vasc Pharmacol. 2014 Mar;12(2):294-9. [Article]
  5. Dechant KL, Goa KL: Calcitriol. A review of its use in the treatment of postmenopausal osteoporosis and its potential in corticosteroid-induced osteoporosis. Drugs Aging. 1994 Oct;5(4):300-17. doi: 10.2165/00002512-199405040-00006. [Article]
  6. Toussaint ND, Damasiewicz MJ: Do the benefits of using calcitriol and other vitamin D receptor activators in patients with chronic kidney disease outweigh the harms? Nephrology (Carlton). 2017 Mar;22 Suppl 2:51-56. doi: 10.1111/nep.13026. [Article]
  7. Farach-Carson MC, Nemere I: Membrane receptors for vitamin D steroid hormones: potential new drug targets. Curr Drug Targets. 2003 Jan;4(1):67-76. [Article]
  8. Brandi L, Egfjord M, Olgaard K: Pharmacokinetics of 1,25(OH)2D3 and 1α(OH)D3 in normal and uraemic men Nephrology Dialysis Transplantation. 2002 May 1;17(5):829–842. [Article]
  9. Takami M, Fujimaki K, Nishimura MI, Iwashima M: Cutting Edge: AhR Is a Molecular Target of Calcitriol in Human T Cells. J Immunol. 2015 Sep 15;195(6):2520-3. doi: 10.4049/jimmunol.1500344. Epub 2015 Aug 14. [Article]
  10. 1,25-DIHYDROXYCHOLECALCIFEROL - National Library of Medicine HSDB Database - ToxNet - NIH [Link]
  11. DailyMed Label: Rocaltrol (calcitriol) Oral Capsule or Solution [Link]
Human Metabolome Database
HMDB0001903
KEGG Drug
D00129
KEGG Compound
C01673
PubChem Compound
5280453
PubChem Substance
46508162
ChemSpider
4444108
BindingDB
50200182
RxNav
1894
ChEBI
17823
ChEMBL
CHEMBL846
ZINC
ZINC000100015048
Therapeutic Targets Database
DAP000289
PharmGKB
PA448717
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
VDX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Calcitriol
PDB Entries
1db1 / 1ie9 / 1rk3 / 2hc4 / 2zbz / 2zlc / 3cv9 / 3m7r / 3vt3 / 3vt7 …
show 9 more
FDA label
Download (39.2 KB)
MSDS
Download (74.7 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedPreventionChronic Kidney Disease (CKD) / Coronary Calcification / Deficiency, Vitamin D / Disorders of Calcium and Bone Metabolism1
4CompletedSupportive CareCancer1
4CompletedTreatmentAnemia / Chronic Kidney Disease (CKD)1
4CompletedTreatmentCardiorenal Syndrome (CRS) / Chronic Allograft Nephropathy (CAN)1
4CompletedTreatmentChronic Kidney Disease (CKD) / Secondary Hyperparathyroidism (SHPT)2

Pharmacoeconomics

Manufacturers
  • Roxane laboratories inc
  • Teva pharmaceuticals usa inc
  • Validus pharmaceuticals llc
  • Abbott laboratories hosp products div
  • Akorn inc
  • App pharmaceuticals llc
  • Fresenius medical care north america
  • Genix therapeutics inc
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Lyne laboratories inc
  • Teva parenteral medicines inc
  • Galderma laboratories lp
Packagers
  • Abbott Laboratories Ltd.
  • Akorn Inc.
  • American Regent
  • APP Pharmaceuticals
  • Atlantic Biologicals Corporation
  • Cardinal Health
  • Catalent Pharma Solutions
  • DSM Corp.
  • F Hoffmann-La Roche Ltd.
  • Galderma Laboratories
  • Gulf Pharmaceutical Industries
  • Hospira Inc.
  • Kaiser Foundation Hospital
  • Luitpold Pharmaceuticals Inc.
  • Nephrx LLC
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Pierre Fabre
  • Ranbaxy Laboratories
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • Validus Pharmaceuticals
Dosage Forms
FormRouteStrength
InjectionIntravenous
Injection, solutionIntravenous1 mcg/ml
Injection, solutionIntravenous2 mcg/mL
Injection, solutionIntravenous; Parenteral1 MCG/ML
SolutionIntravenous2 mcg / mL
InjectionIntravenous1 mcg/ml
InjectionIntravenous2 mcg/ml
CapsuleOral0.25 ug/1
CapsuleOral0.5 ug/1
Capsule, liquid filledOral0.50 ug/1
InjectionIntravenous1 ug/1mL
InjectionIntravenous2 ug/1mL
Injection, solutionIntravenous1 mg/1mL
Injection, solutionIntravenous1 ug/1mL
Injection, solutionIntravenous2 ug/1mL
SolutionIntravenous1 ug/1mL
Capsule, liquid filledOral0.25 cg
Capsule, liquid filledOral0.5 mcg
Capsule, liquid filledOral0.54 mcg
Capsule, liquid filledOral0.6 mcg
Capsule, liquid filledOral0.5 cg
Capsule, liquid filledOral0.3 cg
CapsuleOral0.25 UG
CapsuleOral0.5 UG
SolutionIntravenous1 mcg / mL
CapsuleOral0.25 MICROGRAMMI
CapsuleOral0.50 MICROGRAMMI
CapsuleOral0.5 MICROGRAMMI
Injection, solutionIntravenous
CapsuleOral0.5 Mikrogramm
CapsuleOral0.50 UG
CapsuleOral0.00025 mg
CapsuleOral0.25 mcg
Capsule, liquid filledOral0.25 m
Capsule, liquid filledOral0.25 mcg
CapsuleOral1.5 MG
CapsuleOral3 MG
CapsuleOral4.5 MG
CapsuleOral6 MG
CapsuleOral0.250 mcg
CapsuleOral0.5 mcg
CapsuleOral0.50 MCG
Capsule, gelatin coatedOral0.25 ug/1
Capsule, gelatin coatedOral0.5 ug/1
Capsule, liquid filledOral0.25 ug/1
Capsule, liquid filledOral0.5 ug/1
SolutionOral1 ug/1mL
CapsuleOral
CapsuleOral0.25 MIKROGRAMM
SolutionOral1 mcg / mL
OintmentTopical3 mcg/g
OintmentTopical3 MICROGRAMMI/G
OintmentTopical3 mcg / g
OintmentTopical0.3 mg
KitTopical
OintmentTopical3 ug/1g
Solution1 mcg/1ml
Tablet, delayed releaseOral
Prices
Unit descriptionCostUnit
Calcijex 2 mcg/ml19.38USD ml
Calcijex 1 mcg/ml ampul14.7USD ml
Calcijex 1 mcg/ml10.68USD ml
Calcitriol 1 mcg/ml ampul6.0USD ml
Vectical 3 mcg/g ointment4.68USD g
Rocaltrol 0.5 mcg capsule2.02USD capsule
Calcitriol 0.5 mcg capsule1.97USD capsule
Rocaltrol 0.25 mcg capsule1.46USD capsule
Calcitriol 0.25 mcg capsule1.45USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6265392Yes2001-07-242020-02-02US flag
US6051567Yes2000-04-182020-02-02US flag
US6274169Yes2001-08-142020-02-02US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)113-114Uskokovic, M.R., Narwid, T.A., lacobelli, J.A. and Baggiolini, E.; U.S. Patent 3,993,675; November 23, 1976; assigned to Hoffmann-La Roche, Inc.
water solubilityInsolubleNot Available
logP5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00667 mg/mLALOGPS
logP5.51ALOGPS
logP4.35Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.39Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area60.69 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity126.53 m3·mol-1Chemaxon
Polarizability51.13 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9924
Blood Brain Barrier+0.8524
Caco-2 permeable+0.7812
P-glycoprotein substrateSubstrate0.7843
P-glycoprotein inhibitor INon-inhibitor0.6065
P-glycoprotein inhibitor IINon-inhibitor0.6073
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8367
CYP450 2D6 substrateNon-substrate0.9022
CYP450 3A4 substrateSubstrate0.7506
CYP450 1A2 substrateNon-inhibitor0.9033
CYP450 2C9 inhibitorNon-inhibitor0.8354
CYP450 2D6 inhibitorNon-inhibitor0.9495
CYP450 2C19 inhibitorNon-inhibitor0.7796
CYP450 3A4 inhibitorNon-inhibitor0.813
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6175
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9274
BiodegradationNot ready biodegradable0.9937
Rat acute toxicity5.1352 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8734
hERG inhibition (predictor II)Non-inhibitor0.8579
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0aba-2019200000-f91cfe8e2e00e1a8f6da
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-0219000000-6a6265f9f696ec976c03
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-bdf8e43e790bccc92d4a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kg-2109300000-6c0d3fae8fe566ec7049
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01c0-3229000000-805d017434cf4ee2f1e7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05bf-0409000000-d4b0b29110498da046e5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02mi-2792000000-306b058b5afea2d447a9
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]-220.4513527
predicted
DarkChem Lite v0.1.0
[M-H]-209.1829527
predicted
DarkChem Lite v0.1.0
[M-H]-202.10118
predicted
DeepCCS 1.0 (2019)
[M+H]+214.7668527
predicted
DarkChem Lite v0.1.0
[M+H]+208.8626527
predicted
DarkChem Lite v0.1.0
[M+H]+203.92609
predicted
DeepCCS 1.0 (2019)
[M+Na]+218.9218527
predicted
DarkChem Lite v0.1.0
[M+Na]+208.5045527
predicted
DarkChem Lite v0.1.0
[M+Na]+209.5319
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Vitamin D3 receptor
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]
Details2. Homeobox protein Hox-A10
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sequence-specific transcription factor which is part of a developmental regulatory system that provides cells with specific positional identities on the anterior-posterior axis. Binds to the DNA sequence 5'-AA[AT]TTTTATTAC-3'.
Specific Function
Histone deacetylase binding
Gene Name
HOXA10
Uniprot ID
P31260
Uniprot Name
Homeobox protein Hox-A10
Molecular Weight
42413.825 Da
References
  1. Du H, Daftary GS, Lalwani SI, Taylor HS: Direct regulation of HOXA10 by 1,25-(OH)2D3 in human myelomonocytic cells and human endometrial stromal cells. Mol Endocrinol. 2005 Sep;19(9):2222-33. Epub 2005 May 19. [Article]

Enzymes

Details1. 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
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. 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. Bikle DD: Vitamin D metabolism, mechanism of action, and clinical applications. Chem Biol. 2014 Mar 20;21(3):319-29. doi: 10.1016/j.chembiol.2013.12.016. Epub 2014 Feb 13. [Article]
  3. Anderson PH, O'Loughlin PD, May BK, Morris HA: Determinants of circulating 1,25-dihydroxyvitamin D3 levels: the role of renal synthesis and catabolism of vitamin D. J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):111-3. doi: 10.1016/j.jsbmb.2004.03.089. [Article]
  4. Jones G, Prosser DE, Kaufmann M: 25-Hydroxyvitamin D-24-hydroxylase (CYP24A1): its important role in the degradation of vitamin D. Arch Biochem Biophys. 2012 Jul 1;523(1):9-18. doi: 10.1016/j.abb.2011.11.003. Epub 2011 Nov 12. [Article]
Details2. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Xu Y, Hashizume T, Shuhart MC, Davis CL, Nelson WL, Sakaki T, Kalhorn TF, Watkins PB, Schuetz EG, Thummel KE: Intestinal and hepatic CYP3A4 catalyze hydroxylation of 1alpha,25-dihydroxyvitamin D(3): implications for drug-induced osteomalacia. Mol Pharmacol. 2006 Jan;69(1):56-65. Epub 2005 Oct 5. [Article]

Carriers

Details1. Vitamin D-binding protein
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Vitamin transporter activity
Specific Function
Involved in vitamin D transport and storage, scavenging of extracellular G-actin, enhancement of the chemotactic activity of C5 alpha for neutrophils in inflammation and macrophage activation.
Gene Name
GC
Uniprot ID
P02774
Uniprot Name
Vitamin D-binding protein
Molecular Weight
52963.025 Da
References
  1. Davey RX: Vitamin D-binding protein as it is understood in 2016: is it a critical key with which to help to solve the calcitriol conundrum? Ann Clin Biochem. 2017 Mar;54(2):199-208. doi: 10.1177/0004563216677100. Epub 2016 Dec 11. [Article]
  2. Arnaud J, Constans J: Affinity differences for vitamin D metabolites associated with the genetic isoforms of the human serum carrier protein (DBP). Hum Genet. 1993 Sep;92(2):183-8. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55