Calcitriol
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MedKoo CAT#: 527861

CAS#: 32222-06-3

Description: Calcitriol is the active form of vitamin D, normally made in the kidney. A manufactured form is used to treat kidney disease with low blood calcium, hyperparathyroidism due to kidney disease, low blood calcium due to hypoparathyroidism, osteoporosis, osteomalacia, and familial hypophosphatemia.


Chemical Structure

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Calcitriol
CAS# 32222-06-3

Theoretical Analysis

MedKoo Cat#: 527861
Name: Calcitriol
CAS#: 32222-06-3
Chemical Formula: C27H44O3
Exact Mass: 416.329
Molecular Weight: 416.646
Elemental Analysis: C, 77.84; H, 10.65; O, 11.52

Price and Availability

Size Price Availability Quantity
5.0mg USD 150.0 Ready to ship
10.0mg USD 250.0 Ready to ship
25.0mg USD 450.0 Ready to ship
50.0mg USD 750.0 Ready to ship
100.0mg USD 1250.0 Ready to ship
200.0mg USD 1950.0 Ready to ship
500.0mg USD 2850.0 Ready to ship
1.0g USD 4450.0 Ready to ship
2.0g USD 7550.0 2 Weeks
10.0mM * 1 mL DMSO USD 290.0 Ready to ship
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Synonym: Calcitriol; Rocaltrol; Calcijex; Topitriol; Silkis; Soltriol; 1α,25-Dihydroxyvitamin D3; 1,25-dihydroxycholecalciferol; 1α,25-(OH)2D3; 1,25(OH)2D;

IUPAC/Chemical Name: (1R,3S,Z)-5-(2-((1R,3aS,7aR,E)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol

InChi Key: GMRQFYUYWCNGIN-NKMMMXOESA-N

InChi Code: 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

SMILES Code: C[C@@H]([C@H]1CC[C@H]2/C(CCC[C@]12C)=C/C=C3C[C@H](C[C@@H](C/3=C)O)O)CCCC(C)(O)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Calcitriol is the most active metabolite of vitamin D and also a vitamin D receptor (VDR) agonist.
In vitro activity: This study further investigated the impact of calcitriol on signaling pathways known to regulate CLL (chronic lymphocytic leukemia) cell proliferation and survival. Considering that calcitriol regulates the TLR and PI3K/AKT signaling pathways, this study sought to investigate the activation status of extracellular signal-regulated kinase 1/2 (ERK1/2) and NF-κB p65, both implicated in these pathways. To this end, using intracellular phospho-flow cytometry, this study analyzed pERK1/2 and pNF-κΒ p65 levels in CLL cells supplemented with calcitriol for 24 h and observed a significant increase in pERK (n = 8, FD: 1.6, p < 0.01) (Figure 3A,B), hence contrasting the phosphorylation of NF-κB that was significantly decreased (n = 6, FD: 3.4, p < 0.05) (Figure 3C,D). Reference: Cancers (Basel). 2021 Jan; 13(2): 285. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7828837/
In vivo activity: Compared to lean-V (vehicle) rats, NASH (nonalcoholic steatohepatitis)-V rats were found to have higher levels of plasma TNFα, LBP, and plasma/portal endotoxin, as well as lower levels of plasma/intestinal calcitriol (Table 2). Compared to the NASH-V group, restoration of plasma calcitriol levels in NASH-vit.D rats by 10 weeks of calcitriol treatment was accompanied by the suppression of plasma and portal endotoxin levels as well as the reduction of LBP and TNFα levels (Table 2). Higher TNFα, TNFRI, NFκB, and TLR4 expression in NASH-V rat monocytes than in the lean-V group was observed and this was accompanied by lower vitamin D receptor (VDR) expression (Fig 1D–1F). Significantly, 10 weeks of calcitriol treatment suppressed the TNFα, TNFRI, NFκB and TLR4 expression and normalized VDR expression in the NASH rat monocytes (Fig 1D–1F). Nonetheless, no significant difference in the aforementioned markers was found when lean-V and lean-vit.D groups were compared. Reference: PLoS One. 2018; 13(4): e0194867. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5912737/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 81.0 194.41
Ethanol 61.33 147.2
Methanol 50.0 120.01

Preparing Stock Solutions

The following data is based on the product molecular weight 416.646 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Annamalai C, Seth R, Viswanathan P. Ferrotoxicity and Its Amelioration by Calcitriol in Cultured Renal Cells. Anal Cell Pathol (Amst). 2021 Feb 22;2021:6634429. doi: 10.1155/2021/6634429. PMID: 33680716; PMCID: PMC7925041. 2. Gerousi M, Psomopoulos F, Kotta K, Tsagiopoulou M, Stavroyianni N, Anagnostopoulos A, Anastasiadis A, Gkanidou M, Kotsianidis I, Ntoufa S, Stamatopoulos K. The Calcitriol/Vitamin D Receptor System Regulates Key Immune Signaling Pathways in Chronic Lymphocytic Leukemia. Cancers (Basel). 2021 Jan 14;13(2):285. doi: 10.3390/cancers13020285. PMID: 33466695; PMCID: PMC7828837. 3. Su YB, Li TH, Huang CC, Tsai HC, Huang SF, Hsieh YC, Yang YY, Huang YH, Hou MC, Lin HC. Chronic calcitriol supplementation improves the inflammatory profiles of circulating monocytes and the associated intestinal/adipose tissue alteration in a diet-induced steatohepatitis rat model. PLoS One. 2018 Apr 23;13(4):e0194867. doi: 10.1371/journal.pone.0194867. PMID: 29684027; PMCID: PMC5912737. 4. Srivastava AK, Rizvi A, Cui T, Han C, Banerjee A, Naseem I, Zheng Y, Wani AA, Wang QE. Depleting ovarian cancer stem cells with calcitriol. Oncotarget. 2018 Feb 16;9(18):14481-14491. doi: 10.18632/oncotarget.24520. PMID: 29581858; PMCID: PMC5865684.
In vitro protocol: 1. Annamalai C, Seth R, Viswanathan P. Ferrotoxicity and Its Amelioration by Calcitriol in Cultured Renal Cells. Anal Cell Pathol (Amst). 2021 Feb 22;2021:6634429. doi: 10.1155/2021/6634429. PMID: 33680716; PMCID: PMC7925041. 2. Gerousi M, Psomopoulos F, Kotta K, Tsagiopoulou M, Stavroyianni N, Anagnostopoulos A, Anastasiadis A, Gkanidou M, Kotsianidis I, Ntoufa S, Stamatopoulos K. The Calcitriol/Vitamin D Receptor System Regulates Key Immune Signaling Pathways in Chronic Lymphocytic Leukemia. Cancers (Basel). 2021 Jan 14;13(2):285. doi: 10.3390/cancers13020285. PMID: 33466695; PMCID: PMC7828837.
In vivo protocol: 1. Su YB, Li TH, Huang CC, Tsai HC, Huang SF, Hsieh YC, Yang YY, Huang YH, Hou MC, Lin HC. Chronic calcitriol supplementation improves the inflammatory profiles of circulating monocytes and the associated intestinal/adipose tissue alteration in a diet-induced steatohepatitis rat model. PLoS One. 2018 Apr 23;13(4):e0194867. doi: 10.1371/journal.pone.0194867. PMID: 29684027; PMCID: PMC5912737. 2. Srivastava AK, Rizvi A, Cui T, Han C, Banerjee A, Naseem I, Zheng Y, Wani AA, Wang QE. Depleting ovarian cancer stem cells with calcitriol. Oncotarget. 2018 Feb 16;9(18):14481-14491. doi: 10.18632/oncotarget.24520. PMID: 29581858; PMCID: PMC5865684.

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1: Bartoňková I, Dvořák Z. Assessment of endocrine disruption potential of essential oils of culinary herbs and spices involving glucocorticoid, androgen and vitamin D receptors. Food Funct. 2018 Apr 9. doi: 10.1039/c7fo02058a. [Epub ahead of print] PubMed PMID: 29629442.

2: Richa CG, Saad KJ, Chaaban AK, El Rawas MS. A rare case of hypercalcemia-induced pancreatitis in a first trimester pregnant woman. Endocrinol Diabetes Metab Case Rep. 2018 Mar 28;2018. pii: 17-0175. doi: 10.1530/EDM-17-0175. eCollection 2018. PubMed PMID: 29623207; PubMed Central PMCID: PMC5881426.

3: Al-Dhubaibi MS. Association between Vitamin D deficiency and psoriasis: An exploratory study. Int J Health Sci (Qassim). 2018 Jan-Feb;12(1):33-9. PubMed PMID: 29623015; PubMed Central PMCID: PMC5870311.

4: Maia MLA, Abreu ALS, Nogueira PCK, Val MLDMD, Carvalhaes JTA, Andrade MC. HYPOPHOSPHATEMIC RICKETS: CASE REPORT. Rev Paul Pediatr. 2018 Mar 29:0. doi: 10.1590/1984-0462/;2018;36;2;00009. [Epub ahead of print] Portuguese, English. PubMed PMID: 29617471.

5: Cátia FC, Janete QS, Benedita SM, Liliana SS, Isabel SS, Roberto RA Jr., Manuel P. Calcitriol Prevents Cardiovascular Repercussions in Puromycin Aminonucleoside-Induced Nephrotic Syndrome. Biomed Res Int. 2018 Jan 23;2018:3609645. doi: 10.1155/2018/3609645. eCollection 2018. PubMed PMID: 29607318; PubMed Central PMCID: PMC5828333.

6: Bisson SK, Ung RV, Picard S, Valade D, Agharazii M, Larivière R, Mac-Way F. High calcium, phosphate and calcitriol supplementation leads to an osteocyte-like phenotype in calcified vessels and bone mineralisation defect in uremic rats. J Bone Miner Metab. 2018 Mar 30. doi: 10.1007/s00774-018-0919-y. [Epub ahead of print] PubMed PMID: 29603070.

7: Trummer C, Schwetz V, Pandis M, Grübler MR, Verheyen N, Gaksch M, Zittermann A, März W, Aberer F, Steinkellner J, Friedl C, Brandenburg V, Voelkl J, Alesutan I, Obermayer-Pietsch B, Pieber TR, Tomaschitz A, Pilz S. Effects of vitamin D supplementation on FGF23: a randomized-controlled trial. Eur J Nutr. 2018 Mar 30. doi: 10.1007/s00394-018-1672-7. [Epub ahead of print] PubMed PMID: 29602956.

8: Sølling ASK, Tougaard B, Harsløf T, Langdahl B, Kongsbak Brockstedt H, Byg KE, Ivarsen P, Karstoft Ystrøm I, Holden Mose F, Lissel Isaksson G, Steen Svarer Hansen M, Nagarajah S, Ejersted C, Bendstrup E, Rejnmark L. Non-parathyroid hypercalcemia associated with paraffin oil injection in 12 younger male bodybuilders. Eur J Endocrinol. 2018 Mar 29. pii: EJE-18-0051. doi: 10.1530/EJE-18-0051. [Epub ahead of print] PubMed PMID: 29599408.

9: Dabbaghmanesh MH, Danafar F, Eshraghian A, Omrani GR. Vitamin D supplementation for the treatment of non-alcoholic fatty liver disease: A randomized double blind placebo controlled trial. Diabetes Metab Syndr. 2018 Mar 16. pii: S1871-4021(18)30006-7. doi: 10.1016/j.dsx.2018.03.006. [Epub ahead of print] PubMed PMID: 29588137.

10: Lee MD, Lin CH, Lei WT, Chang HY, Lee HC, Yeung CY, Chiu NC, Chi H, Liu JM, Hsu RJ, Cheng YJ, Yeh TL, Lin CY. Does Vitamin D Deficiency Affect the Immunogenic Responses to Influenza Vaccination? A Systematic Review and Meta-Analysis. Nutrients. 2018 Mar 26;10(4). pii: E409. doi: 10.3390/nu10040409. PubMed PMID: 29587438.

11: Srivastava AK, Rizvi A, Cui T, Han C, Banerjee A, Naseem I, Zheng Y, Wani AA, Wang QE. Depleting ovarian cancer stem cells with calcitriol. Oncotarget. 2018 Feb 16;9(18):14481-14491. doi: 10.18632/oncotarget.24520. eCollection 2018 Mar 6. PubMed PMID: 29581858; PubMed Central PMCID: PMC5865684.

12: He FF, Bao D, Su H, Wang YM, Lei CT, Zhang CY, Ye C, Tang H, Wan C, You CQ, Zhang J, Xiong J, Zhang C. IL-6 increases podocyte motility via MLC-mediated focal adhesion impairment and cytoskeleton disassembly. J Cell Physiol. 2018 Mar 25. doi: 10.1002/jcp.26546. [Epub ahead of print] PubMed PMID: 29574897.

13: Zaheer S, Taquechel K, Brown JM, Adler GK, Williams JS, Vaidya A. A randomized intervention study to evaluate the effect of calcitriol therapy on the renin-angiotensin system in diabetes. J Renin Angiotensin Aldosterone Syst. 2018 Jan-Mar;19(1):1470320317754178. doi: 10.1177/1470320317754178. PubMed PMID: 29562806.

14: Hassoon A, Michos ED, Miller ER, Crisp Z, Appel LJ. Effects of Different Dietary Interventions on Calcitriol, Parathyroid Hormone, Calcium, and Phosphorus: Results from the DASH Trial. Nutrients. 2018 Mar 17;10(3). pii: E367. doi: 10.3390/nu10030367. PubMed PMID: 29562597; PubMed Central PMCID: PMC5872785.

15: Letavernier E, Daudon M. Vitamin D, Hypercalciuria and Kidney Stones. Nutrients. 2018 Mar 17;10(3). pii: E366. doi: 10.3390/nu10030366. Review. PubMed PMID: 29562593; PubMed Central PMCID: PMC5872784.

16: Iseri K, Iyoda M, Watanabe M, Matsumoto K, Sanada D, Inoue T, Tachibana S, Shibata T. The effects of denosumab and alendronate on glucocorticoid-induced osteoporosis in patients with glomerular disease: A randomized, controlled trial. PLoS One. 2018 Mar 15;13(3):e0193846. doi: 10.1371/journal.pone.0193846. eCollection 2018. PubMed PMID: 29543887; PubMed Central PMCID: PMC5854344.

17: Kim HS, Zheng M, Kim DK, Lee WP, Yu SJ, Kim BO. Effects of 1,25-dihydroxyvitamin D(3) on the differentiation of MC3T3-E1 osteoblast-like cells. J Periodontal Implant Sci. 2018 Feb 27;48(1):34-46. doi: 10.5051/jpis.2018.48.1.34. eCollection 2018 Feb. PubMed PMID: 29535889; PubMed Central PMCID: PMC5841266.

18: Li S, Mao J, Wang M, Zhang M, Ni L, Tao Y, Huang B, Chen J. Comparative proteomic analysis of chief and oxyphil cell nodules in refractory uremic hyperparathyroidism by iTRAQ coupled LC-MS/MS. J Proteomics. 2018 May 15;179:42-52. doi: 10.1016/j.jprot.2018.02.029. Epub 2018 Mar 9. PubMed PMID: 29526777.

19: Lau WL, Obi Y, Kalantar-Zadeh K. Parathyroidectomy in the Management of Secondary Hyperparathyroidism. Clin J Am Soc Nephrol. 2018 Mar 9. pii: CJN.10390917. doi: 10.2215/CJN.10390917. [Epub ahead of print] Review. PubMed PMID: 29523679.

20: Meola A, Vignali E, Matrone A, Cetani F, Marcocci C. Efficacy and safety of long-term management of patients with chronic post-surgical hypoparathyroidism. J Endocrinol Invest. 2018 Mar 7. doi: 10.1007/s40618-018-0857-5. [Epub ahead of print] PubMed PMID: 29516386.



Additional Information

Calcitriol increases blood calcium levels ([Ca2+]) by:
(1)Promoting absorption of dietary calcium from the gastrointestinal tract.
(2)Increasing renal tubular reabsorption of calcium, thus reducing the loss of calcium in the urine.
(3)Stimulating release of calcium from bone. For this it acts on the specific type of bone cells referred to as osteoblasts, causing them to release RANKL, which in turn activates osteoclasts.

Calcitriol usually refers specifically to 1,25-dihydroxycholecalciferol. Because cholecalciferol already has one hydroxyl group, only two (1,25) are further specified in this nomenclature, but there are three (1,3,25-triol), as indicated in when calcitriol is used. The 1-hydroxy group is in the alpha position, and this may be specified in the name, for instance in the abbreviation 1α,25-(OH)2D3.
Calcitriol is, strictly, the 1-hydroxylation product of calcifediol (25-OH vitamin D3), derived from cholecalciferol (vitamin D3), rather than the product of hydroxylations of ergocalciferol (vitamin D2). 1α,25-Dihydroxyergocalciferol (ercalcitriol) should be used for the vitamin D2 product.[2] However, the terminology of 1,25-dihydroxyvitamin D, or 1,25(OH)2D, is often used to refer to both types of active forms of vitamin D. Indeed, both bind to the vitamin D receptor and produce biological effects. In clinical use, the differences are unlikely to have major importance.