Calcitriol (CHEM002126)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:07 UTC
Update Date2026-03-26 22:45:53 UTC
Accession NumberCHEM002126
Identification
Common NameCalcitriol
ClassSmall Molecule
DescriptionCalcitriol or 1,25-dihydroxycholecalciferol (abbreviated 1,25-(OH)2-D3) is the active form of vitamin D found in the body (vitamin D3). Calcitriol is marketed under various trade names including Rocaltrol (Roche), Calcijex (Abbott) and Decostriol (Mibe, Jesalis). It is produced in the kidneys via 25-hydroxyvitamin D-1 α-hydroxylase by conversion from 25-hydroxycholecalciferol (calcidiol). This is stimulated by a decrease in serum calcium, phosphate (PO43-) and parathyroid hormone (PTH) levels. It regulates calcium levels by increasing the absorption of calcium and phosphate from the gastrointestinal tract, increasing calcium and phosphate reabsorption in the kidneys and inhibiting the release of PTH. Calcitriol is also commonly used as a medication in the treatment of hypocalcemia and osteoporosis.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antihypocalcemic Agent
  • Antihypoparathyroid Agent
  • Antithyroid Agent
  • Bone Density Conservation Agent
  • Calcium Channel Agonist
  • Drug
  • Essential Vitamin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • Vitamin
  • Vitamin D
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1alpha,3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triolChEBI
(1S,3R,5Z,7E)-9,10-Secocholesta-5,7,10-triene-1,3,25-triolChEBI
(5Z,7E)-(1S,3R)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triolChEBI
1,25-DHCCChEBI
1-alpha-25-Dihydroxyvitamin D3ChEBI
1alpha,25(OH)2D3ChEBI
1alpha,25-DihydroxycholecalciferolChEBI
1alpha,25-Dihydroxyvitamin D3ChEBI
5-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexane-1,3-diolChEBI
CalcijexChEBI
CalcitriolumChEBI
DecostriolChEBI
RocaltrolChEBI
(1S,3R,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-1,3,25-triolKegg
(1a,3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triolGenerator
(1Α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triolGenerator
1-a-25-Dihydroxyvitamin D3Generator
1-Α-25-dihydroxyvitamin D3Generator
1a,25(OH)2D3Generator
1Α,25(OH)2D3Generator
1a,25-DihydroxycholecalciferolGenerator
1Α,25-dihydroxycholecalciferolGenerator
1a,25-Dihydroxyvitamin D3Generator
1Α,25-dihydroxyvitamin D3Generator
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trienetriolHMDB
1,25 DihydroxycholecalciferolHMDB
1,25-DihydroxycholecalciferolHMDB
1,25-Dihydroxyvitamin DHMDB
1,25-Dihydroxyvitamin D3HMDB
1-alpha,25-Dihydroxyvitamin D3HMDB
1a,25-(OH)2D3HMDB
25-DihydroxycholecalciferolHMDB
Dihydroxyvitamin D3HMDB
Ro 21-5535HMDB
SilkisHMDB
SoltriolHMDB
TopitriolHMDB
ToptriolHMDB
1 alpha, 25-Dihydroxy-20-epi-vitamin D3HMDB
1 alpha,25-DihydroxycholecalciferolHMDB
1,25(OH)2-20EPi-D3HMDB
BocatriolHMDB
Calcitriol alphapharm brandHMDB
Calcitriol kyramedHMDB
Calcitriol-nefroHMDB
Hoffmann-la roche brand OF calcitriolHMDB
KyraMed, calcitriolHMDB
TirocalHMDB
alpha,25-Dihydroxyvitamin D3, 1HMDB
1,25-Dihydroxy-20-epi-vitamin D3HMDB
20 Epi 1alpha,25 dihydroxycholecaliferolHMDB
Abbott brand OF calcitriolHMDB
Calcitriol galderma brandHMDB
Calcitriol jenapharm brandHMDB
Calcitriol leo brandHMDB
Cryopharma brand OF calcitriolHMDB
Medice brand OF calcitriolHMDB
RenatriolHMDB
Roche brand OF calcitriolHMDB
1 alpha,25 DihydroxycholecalciferolHMDB
1 alpha,25-Dihydroxyvitamin D3HMDB
20-Epi-1alpha,25-dihydroxycholecaliferolHMDB
Calcitriol gry brandHMDB
Calcitriol kyramed brandHMDB
Calcitriol medice brandHMDB
Calcitriol nefroHMDB
Calcitriol renacare brandHMDB
Calcitriol roche brandHMDB
D3, 1,25-DihydroxyvitaminHMDB
D3, 1,25-Dihydroxy-20-epi-vitaminHMDB
Galderma brand OF calcitriolHMDB
Hoffmann la roche brand OF calcitriolHMDB
KyraMed brand OF calcitriolHMDB
Leo brand OF calcitriolHMDB
RenaCare brand OF calcitriolHMDB
SitriolHMDB
1 alpha, 25 Dihydroxy 20 epi vitamin D3HMDB
1 alpha,25 Dihydroxyvitamin D3HMDB
1,25 Dihydroxyvitamin D3HMDB
1,25 Dihydroxy 20 epi vitamin D3HMDB
Alphapharm brand OF calcitriolHMDB
Calcitriol abbott brandHMDB
Calcitriol cryopharma brandHMDB
CalcitriolNefroHMDB
D3, 1 alpha,25-DihydroxyvitaminHMDB
Gry brand OF calcitriolHMDB
Jenapharm brand OF calcitriolHMDB
OsteotriolHMDB
1a,25-Dihydroxyvitamin D3 / 1a,25-dihydroxycholecalciferol / calcitriolHMDB
1Α,25-dihydroxyvitamin D3 / 1α,25-dihydroxycholecalciferol / calcitriolHMDB
CalcitriolMeSH
Chemical FormulaC27H44O3
Average Molecular Mass416.637 g/mol
Monoisotopic Mass416.329 g/mol
CAS Registry Number32222-06-3
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
Traditional Namecalcitriol
SMILESC[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
InChI IdentifierInChI=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
InChI KeyGMRQFYUYWCNGIN-NKMMMXOESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Adrenal Medulla
  • Bladder
  • Fibroblasts
  • Gonads
  • Gut
  • Intestine
  • Kidney
  • Muscle
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point113-114°C
Boiling PointNot Available
SolubilityInsoluble
Predicted Properties
PropertyValueSource
Water Solubility0.0067 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.53 m³·mol⁻¹ChemAxon
Polarizability51.02 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aba-2019200000-f91cfe8e2e00e1a8f6daSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-2200139000-8f9b07740968867d2e47Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009100000-5d85e3fe2656c4f2c798Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0239000000-16579742f7806ac7c580Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-3297000000-1ded6f55cc278e5facb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0006900000-58dff5fdfef8e2a6c7c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0009300000-93004eb4d3b2dee27fe8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1119000000-a3201818a6bc9ce6cac4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0119000000-f58eb6212ebcce40560eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-4396100000-7177c9113a57f65c8c66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w1-1961000000-2ac1cc3761902eada6c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-67ea14fb7a26b9b2d929Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0505900000-160a8d14ac12dfdfe86eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02k9-0839500000-5c13b18b5994b1b65288Spectrum
Toxicity Profile
Route of ExposureIntravenous, Oral. Rapidly absorbed from the intestine.
Mechanism of ToxicityThe 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.
MetabolismThe 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. The lactone appears to be the major metabolite circulating in humans. Route of Elimination: Enterohepatic recycling and biliary excretion of calcitriol occur. 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. Half Life: 5-8 hours
Toxicity ValuesLD50 (oral, rat) = 620 μg/kg; LD50 (intraperitoneal, rat) > 5 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed 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.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsOverdose evident in elevated blood calcium levels causing symptoms of anorexia, nausea and vomiting, polyuria, polydipsia, weakness, pruritus, and nervousness, potentially with irreversible calcification of soft tissue in the kidney and liver.
TreatmentThe treatment of acute accidental overdosage of Calcitriol should consist of general supportive measures. If drug ingestion is discovered within a relatively short time, induction of emesis or gastric lavage may be of benefit in preventing further absorption. If the drug has passed through the stomach, the administration of mineral oil may promote its fecal elimination. Serial serum electrolyte determinations (especially calcium), rate of urinary calcium excretion, and assessment of electrocardiographic abnormalities due to hypercalcemia should be obtained. Such monitoring is critical in patients receiving digitalis. Discontinuation of supplemental calcium and a low-calcium diet are also indicated in accidental overdosage. (13)
Concentrations
Not Available
DrugBank IDDB00136
HMDB IDHMDB0001903
FooDB IDFDB021822
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2289241
BioCyc IDCALCITRIOL
METLIN ID6382
PDB IDNot Available
Wikipedia LinkCalcitriol
Chemspider ID4444108
ChEBI ID17823
PubChem Compound ID5280453
Kegg Compound IDC01673
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

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

MSDSLink
General References
1. Chen, Yang-sheng; Zhai, Cui-yun; Ren, Li. Synthesis of calcitriol. Zhongguo Xinyao Zazhi (2005), 14(1), 69-72.
2. Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240.
3. Chen, Yang-sheng; Zhai, Cui-yun; Ren, Li. Synthesis of calcitriol. Zhongguo Xinyao Zazhi (2005), 14(1), 69-72.
4. Shepard RM, Horst RL, Hamstra AJ, DeLuca HF: Determination of vitamin D and its metabolites in plasma from normal and anephric man. Biochem J. 1979 Jul 15;182(1):55-69.
5. Mason RS, Frankel T, Chan YL, Lissner D, Posen S: Vitamin D conversion by sarcoid lymph node homogenate. Ann Intern Med. 1984 Jan;100(1):59-61.
6. Mallette LE: Case report: hypoparathyroidism with menses-associated hypocalcemia. Am J Med Sci. 1992 Jul;304(1):32-7.
7. Ott SM, Chesnut CH 3rd: Calcitriol treatment is not effective in postmenopausal osteoporosis. Ann Intern Med. 1989 Feb 15;110(4):267-74.
8. Bhan I, Shah A, Holmes J, Isakova T, Gutierrez O, Burnett SM, Juppner H, Wolf M: Post-transplant hypophosphatemia: Tertiary 'Hyper-Phosphatoninism'? Kidney Int. 2006 Oct;70(8):1486-94. Epub 2006 Aug 30.
9. Josephson MA, Schumm LP, Chiu MY, Marshall C, Thistlethwaite JR, Sprague SM: Calcium and calcitriol prophylaxis attenuates posttransplant bone loss. Transplantation. 2004 Oct 27;78(8):1233-6.
10. Gallagher JC, Goldgar D: Treatment of postmenopausal osteoporosis with high doses of synthetic calcitriol. A randomized controlled study. Ann Intern Med. 1990 Nov 1;113(9):649-55.
11. Lehmann B, Sauter W, Knuschke P, Dressler S, Meurer M: Demonstration of UVB-induced synthesis of 1 alpha,25-dihydroxyvitamin D3 (calcitriol) in human skin by microdialysis. Arch Dermatol Res. 2003 Apr;295(1):24-8. Epub 2003 Mar 11.
12. Moreno J, Krishnan AV, Swami S, Nonn L, Peehl DM, Feldman D: Regulation of prostaglandin metabolism by calcitriol attenuates growth stimulation in prostate cancer cells. Cancer Res. 2005 Sep 1;65(17):7917-25.
13. Kalkwarf HJ, Specker BL, Heubi JE, Vieira NE, Yergey AL: Intestinal calcium absorption of women during lactation and after weaning. Am J Clin Nutr. 1996 Apr;63(4):526-31.
14. Mason RS, Lissner D, Grunstein HS, Posen S: A simplified assay for dihydroxylated vitamin D metabolites in human serum: application to hyper- and hypovitaminosis D. Clin Chem. 1980 Mar;26(3):444-50.
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=10217585
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=15928596
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=19429426
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=20599255
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22905919
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23103122
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23144765
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=6687801