Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C33H54O8 |
| Molecular Weight | 578.7771 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@H](C[C@H](O)C3=C)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O
InChI
InChIKey=UCQHUTIFFMTBFB-DAHKFYDDSA-N
InChI=1S/C33H54O8/c1-19(8-6-14-32(3,4)39)24-12-13-25-21(9-7-15-33(24,25)5)10-11-22-16-23(17-26(35)20(22)2)40-31-30(38)29(37)28(36)27(18-34)41-31/h10-11,19,23-31,34-39H,2,6-9,12-18H2,1,3-5H3/b21-10+,22-11-/t19-,23-,24-,25+,26+,27-,28-,29+,30-,31-,33-/m1/s1
| Molecular Formula | C33H54O8 |
| Molecular Weight | 578.7771 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 11 / 11 |
| 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.
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 |
|---|---|---|---|---|
| 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 Date1978 |
|||
| 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 Date1978 |
|||
| Primary | VECTICAL Approved UseVECTICAL Ointment is indicated for the topical treatment of mild to moderate plaque psoriasis in adults 18 years and older. Launch Date1978 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
73.18 pg/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
2 mg/cm² 2 times / day multiple, topical dose: 2 mg/cm² 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 |
2 mg/cm² single, topical dose: 2 mg/cm² route of administration: topical experiment type: single co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
549.29 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
2 mg/cm² 2 times / day multiple, topical dose: 2 mg/cm² route of administration: topical experiment type: multiple co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
|
737.74 pg*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00419666 |
2 mg/cm² 2 times / day multiple, topical dose: 2 mg/cm² 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 |
2 mg/cm² single, topical dose: 2 mg/cm² route of administration: topical experiment type: single 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 |
2 mg/cm² single, topical dose: 2 mg/cm² route of administration: topical experiment type: single co-administered: |
CALCITRIOL plasma | Homo sapiens population: unhealthy age: Adolescents sex: F+M food status: |
|
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 |
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 |
|---|---|---|
| Androgen receptor signaling and vitamin D receptor action in prostate cancer cells. | 2005-09-01 |
|
| Vitamin D and phosphate regulate fibroblast growth factor-23 in K-562 cells. | 2005-06 |
|
| 5alpha-dihydrotestosterone inhibits 1alpha,25-dihydroxyvitamin D3-induced expression of CYP24 in human prostate cancer cells. | 2005-05-15 |
|
| Regulation of renal calcium receptor gene expression by 1,25-dihydroxyvitamin D3 in genetic hypercalciuric stone-forming rats. | 2005-05 |
|
| 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. | 2005-04-01 |
|
| Modulation of CYP27B1 and CYP24 mRNA expression in bone is independent of circulating 1,25(OH)2D3 levels. | 2005-04 |
|
| Daily or intermittent calcitriol administration during growth hormone therapy in rats with renal failure and advanced secondary hyperparathyroidism. | 2005-04 |
|
| Mechanism and function of high vitamin D receptor levels in genetic hypercalciuric stone-forming rats. | 2005-03 |
|
| Pretreatment serum FGF-23 levels predict the efficacy of calcitriol therapy in dialysis patients. | 2005-03 |
|
| Amphiregulin is a novel growth factor involved in normal bone development and in the cellular response to parathyroid hormone stimulation. | 2005-02-04 |
|
| 1,25-Dihydroxyvitamin D3 stimulates cyclic vitamin D receptor/retinoid X receptor DNA-binding, co-activator recruitment, and histone acetylation in intact osteoblasts. | 2005-02 |
|
| Human bladder as a novel target for vitamin D receptor ligands. | 2005-02 |
|
| Regulation of the human vitamin D3 receptor promoter in breast cancer cells is mediated through Sp1 sites. | 2005-01-31 |
|
| Circulating FGF-23 is regulated by 1alpha,25-dihydroxyvitamin D3 and phosphorus in vivo. | 2005-01-28 |
|
| Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative. | 2005-01 |
|
| Type 2 iodothyronine selenodeiodinase is expressed throughout the mouse skeleton and in the MC3T3-E1 mouse osteoblastic cell line during differentiation. | 2005-01 |
|
| Targacept active conformation search: a new method for predicting the conformation of a ligand bound to its protein target. | 2004-12-30 |
|
| Calcitriol-induced prostate-derived factor: autocrine control of prostate cancer cell growth. | 2004-12-20 |
|
| The functional consequences of cross-talk between the vitamin D receptor and ERK signaling pathways are cell-specific. | 2004-11-05 |
|
| Calcium and calcitriol prophylaxis attenuates posttransplant bone loss. | 2004-10-27 |
|
| Role of uncoupling protein 2 (UCP2) expression and 1alpha, 25-dihydroxyvitamin D3 in modulating adipocyte apoptosis. | 2004-09 |
|
| Unique regulation of SOST, the sclerosteosis gene, by BMPs and steroid hormones in human osteoblasts. | 2004-08 |
|
| Possible involvement of circulating fibroblast growth factor 23 in the development of secondary hyperparathyroidism associated with renal insufficiency. | 2004-08 |
|
| Gene expression analysis suggests that 1,25-dihydroxyvitamin D3 reverses experimental autoimmune encephalomyelitis by stimulating inflammatory cell apoptosis. | 2004-07-08 |
|
| Differential regulation of osteogenic marker gene expression by Wnt-3a in embryonic mesenchymal multipotential progenitor cells. | 2004-06 |
|
| Improved anemia and reduced erythropoietin need by medical or surgical intervention of secondary hyperparathyroidism in hemodialysis patients. | 2004-05 |
|
| DNA microarray analysis of vitamin D-induced gene expression in a human colon carcinoma cell line. | 2004-04-13 |
|
| FGF-23 is a potent regulator of vitamin D metabolism and phosphate homeostasis. | 2004-03 |
|
| 1,25(OH)2D3 inhibits bone marrow adipogenesis in senescence accelerated mice (SAM-P/6) by decreasing the expression of peroxisome proliferator-activated receptor gamma 2 (PPARgamma2). | 2004-03 |
|
| Leptin corrects increased gene expression of renal 25-hydroxyvitamin D3-1 alpha-hydroxylase and -24-hydroxylase in leptin-deficient, ob/ob mice. | 2004-03 |
|
| Targeted ablation of Fgf23 demonstrates an essential physiological role of FGF23 in phosphate and vitamin D metabolism. | 2004-02 |
|
| Retinoblastoma protein and CCAAT/enhancer-binding protein beta are required for 1,25-dihydroxyvitamin D3-induced monocytic differentiation of HL60 cells. | 2004-01-01 |
|
| Structural determinants for vitamin D receptor response to endocrine and xenobiotic signals. | 2004-01 |
|
| Vitamin D inhibits G1 to S progression in LNCaP prostate cancer cells through p27Kip1 stabilization and Cdk2 mislocalization to the cytoplasm. | 2003-11-21 |
|
| Previtamin D3 with a trans-fused decalin CD-ring has pronounced genomic activity. | 2003-09-12 |
|
| 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. | 2003-08-15 |
|
| Comparison of the gene expression profiles of monocytic versus granulocytic lineages of HL-60 leukemia cell differentiation by DNA microarray analysis. | 2003-08-15 |
|
| Effects of Seocalcitol (EB1089) on nitrosomethyl urea-induced rat mammary tumors. | 2003-08 |
|
| Gene expression of vitamin D hydroxylase and megalin in the remnant kidney of nephrectomized rats. | 2003-08 |
|
| Vitamin D enhances mitogenesis mediated by keratinocyte growth factor receptor in keratinocytes. | 2003-06-01 |
|
| 1alpha,25(OH)2D3 causes a rapid increase in phosphatidylinositol-specific PLC-beta activity via phospholipase A2-dependent production of lysophospholipid. | 2003-05 |
|
| Inhibition of fatty acid synthase expression by 1alpha,25-dihydroxyvitamin D3 in prostate cancer cells. | 2003-05 |
|
| Regulation of 1-alpha, 25-dihydroxyvitamin D3 on interleukin-6 and interleukin-8 induced by sulfur mustard (HD) on human skin cells. | 2003-05 |
|
| Demonstration of UVB-induced synthesis of 1 alpha,25-dihydroxyvitamin D3 (calcitriol) in human skin by microdialysis. | 2003-04 |
|
| Paricalcitol versus calcitriol in the treatment of secondary hyperparathyroidism. | 2003-04 |
|
| EB1089: a new vitamin D analogue that inhibits the growth of breast cancer cells in vivo and in vitro. | 1992-12-15 |
|
| Potentiation of lipopolysaccharide-induced tumor necrosis factor-alpha expression by 1,25-dihydroxyvitamin D3. | 1992-12-01 |
|
| Dose-dependent effects of aluminum on osteocalcin synthesis in osteoblast-like ROS 17/2 cells in culture. | 1992-12 |
|
| A prospective trial of phosphate and 1,25-dihydroxyvitamin D3 therapy in symptomatic adults with X-linked hypophosphatemic rickets. | 1992-09 |
|
| Effect of 1,25-dihydroxyvitamin D3 on the female reproductive system in rats. | 1992-08 |
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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Edited
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| Record UNII |
4HF9ADM3YJ
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| Record Status |
Validated (UNII)
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| Record Version |
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