Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H44O3 |
Molecular Weight | 416.6375 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]([H])(CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])/C(=C(\[H])/C(/[H])=C\3/C[C@]([H])(C[C@@]([H])(C3=C)O)O)/CCC[C@]12C
InChI
InChIKey=GMRQFYUYWCNGIN-NKMMMXOESA-N
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
Molecular Formula | C27H44O3 |
Molecular Weight | 416.6375 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/mesh/68002117 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/021068a_phrmr_P1.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/1998/21068lbl.pdfCurator's Comment:: description was created based on several sources, including:
https://www.drugs.com/cdi/calcitriol.html
http://www.wikidoc.org/index.php/Calcitriol_(oral)
Sources: https://www.ncbi.nlm.nih.gov/mesh/68002117 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/021068a_phrmr_P1.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/1998/21068lbl.pdf
Curator's Comment:: description was created based on several sources, including:
https://www.drugs.com/cdi/calcitriol.html
http://www.wikidoc.org/index.php/Calcitriol_(oral)
Calcitriol is vitamin D3. Vitamin D is important for the absorption of calcium from the stomach and for the functioning of calcium in the body. Calcitriol is used to treat hyperparathyroidism (overactive parathyroid glands) and metabolic bone disease in people who have chronic kidney failure and are not receiving dialysis. Calcitriol is also used to treat calcium deficiency (hypocalcemia). The early signs and symptoms of vitamin D intoxication associated with hypercalcemia include: weakness, headache, somnolence, nausea, vomiting, dry mouth, constipation, muscle pain, bone pain and metallic taste. Cholestyramine has been reported to reduce intestinal absorption of fatsoluble vitamins; as such it may impair intestinal absorption of Calcitriol. Ketoconazole may inhibit both synthetic and catabolic enzymes of calcitriol.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4313704
Curator's Comment:: First obtained from chick intestine and designated as metabolite 4B
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P11473 Gene ID: 7421.0 Gene Symbol: VDR Target Organism: Homo sapiens (Human) |
0.22 nM [Kd] | ||
Target ID: CHEMBL340 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ROCALTROL Approved UsePredialysis Patients Calcitriol Capsules are indicated in the management of secondary hyperparathyroidism and resultant metabolic bone disease in patients with moderate to severe chronic renal failure (Ccr 15 to 55 mL/min) not yet on dialysis. In children, the creatinine clearance value must be corrected for a surface area of 1.73 square meters. A serum iPTH level of ≥100 pg/mL is strongly suggestive of secondary hyperparathyroidism. Dialysis Patients Calcitriol Capsules are indicated in the management of hypocalcemia and the resultant metabolic bone disease in patients undergoing chronic renal dialysis. In these patients, calcitriol administration enhances calcium absorption, reduces serum alkaline phosphatase levels, and may reduce elevated parathyroid hormone levels and the histological manifestations of osteitis fibrosa cystica and defective mineralization. Hypoparathyroidism Patients Calcitriol Capsules are also indicated in the management of hypocalcemia and its clinical manifestations in patients with postsurgical hypoparathyroidism, idiopathic hypoparathyroidism, and pseudohypoparathyroidism. Launch Date2.72159998E11 |
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Preventing | ROCALTROL Approved UsePredialysis Patients Calcitriol Capsules are indicated in the management of secondary hyperparathyroidism and resultant metabolic bone disease in patients with moderate to severe chronic renal failure (Ccr 15 to 55 mL/min) not yet on dialysis. In children, the creatinine clearance value must be corrected for a surface area of 1.73 square meters. A serum iPTH level of ≥100 pg/mL is strongly suggestive of secondary hyperparathyroidism. Dialysis Patients Calcitriol Capsules are indicated in the management of hypocalcemia and the resultant metabolic bone disease in patients undergoing chronic renal dialysis. In these patients, calcitriol administration enhances calcium absorption, reduces serum alkaline phosphatase levels, and may reduce elevated parathyroid hormone levels and the histological manifestations of osteitis fibrosa cystica and defective mineralization. Hypoparathyroidism Patients Calcitriol Capsules are also indicated in the management of hypocalcemia and its clinical manifestations in patients with postsurgical hypoparathyroidism, idiopathic hypoparathyroidism, and pseudohypoparathyroidism. Launch Date2.72159998E11 |
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Primary | VECTICAL Approved UseVECTICAL Ointment is indicated for the topical treatment of mild to moderate plaque psoriasis in adults 18 years and older. Launch Date2.72159998E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1100 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12496746 |
38 μg 3 times / week multiple, oral dose: 38 μg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL |
CALCITRIOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
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73.1799999999999 pg/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
3 ug/g 2 times / day multiple, topical dose: 3 ug/g route of administration: topical experiment type: multiple co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
|
75.74 pg/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
3 ug/g single, topical dose: 3 ug/g route of administration: topical experiment type: single co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8100 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12496746 |
38 μg 3 times / week multiple, oral dose: 38 μg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL |
CALCITRIOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
737.74 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
3 ug/g 2 times / day multiple, topical dose: 3 ug/g route of administration: topical experiment type: multiple co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
|
764.74 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
3 ug/g single, topical dose: 3 ug/g route of administration: topical experiment type: single co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
|
549.29 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
3 ug/g 2 times / day multiple, topical dose: 3 ug/g route of administration: topical experiment type: multiple co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
|
575.12 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
3 ug/g single, topical dose: 3 ug/g route of administration: topical experiment type: single co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12496746 |
38 μg 3 times / week multiple, oral dose: 38 μg route of administration: Oral experiment type: MULTIPLE co-administered: PACLITAXEL |
CALCITRIOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of 1,25-dihydroxyvitamin D3 on the female reproductive system in rats. | 1992 Aug |
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Dose-dependent effects of aluminum on osteocalcin synthesis in osteoblast-like ROS 17/2 cells in culture. | 1992 Dec |
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Potentiation of lipopolysaccharide-induced tumor necrosis factor-alpha expression by 1,25-dihydroxyvitamin D3. | 1992 Dec 1 |
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EB1089: a new vitamin D analogue that inhibits the growth of breast cancer cells in vivo and in vitro. | 1992 Dec 15 |
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A prospective trial of phosphate and 1,25-dihydroxyvitamin D3 therapy in symptomatic adults with X-linked hypophosphatemic rickets. | 1992 Sep |
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Zinc increases the activity of vitamin D-dependent promoters in osteoblasts. | 2000 Apr 29 |
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Calcitriol-induced apoptosis in LNCaP cells is blocked by overexpression of Bcl-2. | 2000 Jan |
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1alpha,25-dihydroxyvitamin D3 inhibits prostate cancer cell growth by androgen-dependent and androgen-independent mechanisms. | 2000 Jul |
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Regulation of vitamin D-1alpha-hydroxylase and -24-hydroxylase expression by dexamethasone in mouse kidney. | 2000 Mar |
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Combination of 1alpha,25-dihydroxyvitamin D(3) with dexamethasone enhances cell cycle arrest and apoptosis: role of nuclear receptor cross-talk and Erk/Akt signaling. | 2001 Dec |
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Failure of high doses of calcitriol and hypercalcaemia to induce apoptosis in hyperplastic parathyroid glands of azotaemic rats. | 2001 Mar |
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1 alpha,25-Dihydroxycholecalciferol reduces rejection and improves survival in rat liver allografts. | 2001 Nov |
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Regression of ventral striatum hypometabolism after calcium/calcitriol therapy in paroxysmal kinesigenic choreoathetosis due to idiopathic primary hypoparathyroidism. | 2001 Nov |
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Hyperphosphatemia modestly retards parathyroid hormone suppression during calcitriol-induced hypercalcemia in normal and azotemic rats. | 2002 Dec |
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Demonstration of UVB-induced synthesis of 1 alpha,25-dihydroxyvitamin D3 (calcitriol) in human skin by microdialysis. | 2003 Apr |
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Effects of Seocalcitol (EB1089) on nitrosomethyl urea-induced rat mammary tumors. | 2003 Aug |
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Gene expression of vitamin D hydroxylase and megalin in the remnant kidney of nephrectomized rats. | 2003 Aug |
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9-cis retinoic acid accelerates calcitriol-induced osteocalcin production and promotes degradation of both vitamin D receptor and retinoid X receptor in human osteoblastic cells. | 2003 Aug 15 |
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Comparison of the gene expression profiles of monocytic versus granulocytic lineages of HL-60 leukemia cell differentiation by DNA microarray analysis. | 2003 Aug 15 |
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Vitamin D enhances mitogenesis mediated by keratinocyte growth factor receptor in keratinocytes. | 2003 Jun 1 |
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1alpha,25(OH)2D3 causes a rapid increase in phosphatidylinositol-specific PLC-beta activity via phospholipase A2-dependent production of lysophospholipid. | 2003 May |
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Vitamin D inhibits G1 to S progression in LNCaP prostate cancer cells through p27Kip1 stabilization and Cdk2 mislocalization to the cytoplasm. | 2003 Nov 21 |
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Previtamin D3 with a trans-fused decalin CD-ring has pronounced genomic activity. | 2003 Sep 12 |
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Unique regulation of SOST, the sclerosteosis gene, by BMPs and steroid hormones in human osteoblasts. | 2004 Aug |
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Possible involvement of circulating fibroblast growth factor 23 in the development of secondary hyperparathyroidism associated with renal insufficiency. | 2004 Aug |
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Calcitriol-induced prostate-derived factor: autocrine control of prostate cancer cell growth. | 2004 Dec 20 |
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Targacept active conformation search: a new method for predicting the conformation of a ligand bound to its protein target. | 2004 Dec 30 |
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Targeted ablation of Fgf23 demonstrates an essential physiological role of FGF23 in phosphate and vitamin D metabolism. | 2004 Feb |
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Structural determinants for vitamin D receptor response to endocrine and xenobiotic signals. | 2004 Jan |
|
Retinoblastoma protein and CCAAT/enhancer-binding protein beta are required for 1,25-dihydroxyvitamin D3-induced monocytic differentiation of HL60 cells. | 2004 Jan 1 |
|
Differential regulation of osteogenic marker gene expression by Wnt-3a in embryonic mesenchymal multipotential progenitor cells. | 2004 Jun |
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Leptin corrects increased gene expression of renal 25-hydroxyvitamin D3-1 alpha-hydroxylase and -24-hydroxylase in leptin-deficient, ob/ob mice. | 2004 Mar |
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Improved anemia and reduced erythropoietin need by medical or surgical intervention of secondary hyperparathyroidism in hemodialysis patients. | 2004 May |
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The functional consequences of cross-talk between the vitamin D receptor and ERK signaling pathways are cell-specific. | 2004 Nov 5 |
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Calcium and calcitriol prophylaxis attenuates posttransplant bone loss. | 2004 Oct 27 |
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Role of uncoupling protein 2 (UCP2) expression and 1alpha, 25-dihydroxyvitamin D3 in modulating adipocyte apoptosis. | 2004 Sep |
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Modulation of CYP27B1 and CYP24 mRNA expression in bone is independent of circulating 1,25(OH)2D3 levels. | 2005 Apr |
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Daily or intermittent calcitriol administration during growth hormone therapy in rats with renal failure and advanced secondary hyperparathyroidism. | 2005 Apr |
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Molecular and functional comparison of 1,25-dihydroxyvitamin D(3) and the novel vitamin D receptor ligand, lithocholic acid, in activating transcription of cytochrome P450 3A4. | 2005 Apr 1 |
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1,25-Dihydroxyvitamin D3 stimulates cyclic vitamin D receptor/retinoid X receptor DNA-binding, co-activator recruitment, and histone acetylation in intact osteoblasts. | 2005 Feb |
|
Human bladder as a novel target for vitamin D receptor ligands. | 2005 Feb |
|
Amphiregulin is a novel growth factor involved in normal bone development and in the cellular response to parathyroid hormone stimulation. | 2005 Feb 4 |
|
Circulating FGF-23 is regulated by 1alpha,25-dihydroxyvitamin D3 and phosphorus in vivo. | 2005 Jan 28 |
|
Regulation of the human vitamin D3 receptor promoter in breast cancer cells is mediated through Sp1 sites. | 2005 Jan 31 |
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Vitamin D and phosphate regulate fibroblast growth factor-23 in K-562 cells. | 2005 Jun |
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Mechanism and function of high vitamin D receptor levels in genetic hypercalciuric stone-forming rats. | 2005 Mar |
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Pretreatment serum FGF-23 levels predict the efficacy of calcitriol therapy in dialysis patients. | 2005 Mar |
|
Regulation of renal calcium receptor gene expression by 1,25-dihydroxyvitamin D3 in genetic hypercalciuric stone-forming rats. | 2005 May |
|
5alpha-dihydrotestosterone inhibits 1alpha,25-dihydroxyvitamin D3-induced expression of CYP24 in human prostate cancer cells. | 2005 May 15 |
|
Androgen receptor signaling and vitamin D receptor action in prostate cancer cells. | 2005 Sep 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment:: The recommended initial dose of Calcitriol Injection, depending on the severity of the hypocalcemia and/or secondary hyperparathyroidism, is 1 mcg (0.02 mcg/kg) to 2 mcg administered intravenously three times weekly, approximately every other day. Doses as small as 0.5 mcg and as large as 4 mcg three times weekly have been used as an initial dose.
Apply Calcitriol Ointment to affected areas twice daily, morning and evening. The maximum weekly dose should not exceed 200 grams. Calcitriol Ointment is not for oral, ophthalmic or intravaginal use.
Mice: Trans-calcitriol at 1.0, 2.0, and 4.0 mg/kg did not elicit any clinical effects after a single oral dose followed by 14 days of observation.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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admin
on
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on
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Record UNII |
FXC9231JVH
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000006996
Created by
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WHO-VATC |
QD05AX03
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NCI_THESAURUS |
C39713
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LOINC |
1649-3
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LIVERTOX |
140
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NDF-RT |
N0000006996
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WHO-ATC |
A11CC04
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NDF-RT |
N0000006996
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NDF-RT |
N0000006996
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LOINC |
14566-4
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NDF-RT |
N0000175908
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WHO-VATC |
QA11CC04
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WHO-ATC |
D05AX03
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NCI_THESAURUS |
C1934
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2779
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250-963-8
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5280453
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CALCITRIOL
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M2917
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DB00136
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D002117
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32222-06-3
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4393
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CHEMBL846
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466
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C330
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3482
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SUB06047MIG
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1086301
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1894
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PRIMARY | RxNorm | ||
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FXC9231JVH
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Calcitriol
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32222-06-3
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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BASIS OF STRENGTH->SUBSTANCE |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
The conversion of calcidiol to calcitriol is catalyzed by the enzyme 25-hydroxyvitamin D3 1-alpha-hydroxylase (CYP27B1).
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METABOLITE INACTIVE -> PARENT |
MAJOR
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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