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
[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@H](C[C@H](O)C3=C)O[C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](C)CCCC(C)(C)O
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
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/21068lbl.pdfhttps://www.ncbi.nlm.nih.gov/mesh/68002117 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/021068a_phrmr_P1.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: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/21068lbl.pdfhttps://www.ncbi.nlm.nih.gov/mesh/68002117 | https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/021068a_phrmr_P1.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)
Trans-calcitriol or Calcitriol Impurity A, is the impurity of Calcitriol. Calcitriol is the hormonally active form of vitamin D, Calcitriol is the active metabolite of vitamin D3 that activates the vitamin D receptor (VDR). Calcitriol Impurity A is the physiologically active form of vitamin D. It is formed primarily in the kidney by enzymatic hydroxylation of 25-hydroxycholecalciferol (CALCIFEDIOL). Its production is stimulated by low blood calcium levels and parathyroid hormone. Calcitriol increases intestinal absorption of calcium and phosphorus, and in concert with parathyroid hormone increases bone resorption.
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 |
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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 Date1978 |
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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 Date1978 |
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 |
|
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 |
|---|---|---|
| Dose-dependent effects of aluminum on osteocalcin synthesis in osteoblast-like ROS 17/2 cells in culture. | 1992 Dec |
|
| Calcitriol-mediated hypercalcaemia and increased interleukins in a patient with sarcoid myopathy. | 1999 |
|
| Hypercalcemia-induced renal insufficiency during therapy with dihydrotachysterol. | 1999 |
|
| 1,25 dihydroxyvitamin D3 enhances the calcium response of keratinocytes. | 1999 Feb |
|
| Hypercalcaemia and hypercalciuria after topical treatment of psoriasis with excessive amounts of calcipotriol. | 1999 Jan |
|
| Effectiveness of 1,25-dihydroxyvitamin D supplementation on blood pressure reduction in a pseudohypoparathyroidism patient with high renin activity. | 1999 Jan |
|
| A Phase I trial of calcitriol (1,25-dihydroxycholecalciferol) in patients with advanced malignancy. | 1999 Jun |
|
| Calcitriol directly sensitizes renal tubular cells to ATP-depletion- and iron-mediated attack. | 1999 Jun |
|
| Antineoplastic effect and toxicity of 1,25-dihydroxy-16-ene-23-yne-vitamin D3 in athymic mice with Y-79 human retinoblastoma tumors. | 1999 Mar |
|
| 22-oxacalcitriol suppresses secondary hyperparathyroidism without inducing low bone turnover in dogs with renal failure. | 1999 Mar |
|
| 20-Cyclopropyl-cholecalciferol vitamin D3 analogs: a unique class of potent inhibitors of proliferation of human prostate, breast and myeloid leukemia cell lines. | 1999 May-Jun |
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| Calcitriol-induced apoptosis in LNCaP cells is blocked by overexpression of Bcl-2. | 2000 Jan |
|
| New vitamin D receptor agonists with decreased metabolic stability. | 2000 Jun 15 |
|
| 1 Alpha,25-dihydroxyvitamin D3 inhibits differentiation, maturation, activation, and survival of dendritic cells leading to impaired alloreactive T cell activation. | 2000 Mar 1 |
|
| Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2). | 2001 |
|
| Beneficial effect of 1,25 dihydroxyvitamin D3 on cytokine-treated human pancreatic islets. | 2001 Apr |
|
| Carnosic acid and promotion of monocytic differentiation of HL60-G cells initiated by other agents. | 2001 Aug 15 |
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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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| The anti-proliferative effect of calcitriol on HL-60 cells is neutralized by uraemic biological fluids. | 2001 Feb |
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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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| 1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects. | 2001 May |
|
| Apoptosis induction by 1alpha,25-dihydroxyvitamin D3 in prostate cancer. | 2002 Jul |
|
| Novel detection and differential utilization of a c-myc transcriptional block in colon cancer chemoprevention. | 2002 Nov 1 |
|
| Paricalcitol versus calcitriol in the treatment of secondary hyperparathyroidism. | 2003 Apr |
|
| 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 |
|
| Regulation of 1-alpha, 25-dihydroxyvitamin D3 on interleukin-6 and interleukin-8 induced by sulfur mustard (HD) on human skin cells. | 2003 May |
|
| Vitamin D inhibits G1 to S progression in LNCaP prostate cancer cells through p27Kip1 stabilization and Cdk2 mislocalization to the cytoplasm. | 2003 Nov 21 |
|
| DNA microarray analysis of vitamin D-induced gene expression in a human colon carcinoma cell line. | 2004 Apr 13 |
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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 |
|
| 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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| Modulation of CYP27B1 and CYP24 mRNA expression in bone is independent of circulating 1,25(OH)2D3 levels. | 2005 Apr |
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| Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative. | 2005 Jan |
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| Regulation of the human vitamin D3 receptor promoter in breast cancer cells is mediated through Sp1 sites. | 2005 Jan 31 |
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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 |
|
| 5alpha-dihydrotestosterone inhibits 1alpha,25-dihydroxyvitamin D3-induced expression of CYP24 in human prostate cancer cells. | 2005 May 15 |
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.
Calcitriol can be administered orally either as a capsule (0.25 mcg or 0.50 mcg) or as an oral solution (1 mcg/mL).
Route of Administration:
Other
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89497-11-0
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4HF9ADM3YJ
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21764985
Created by
admin on Sat Dec 16 14:21:34 GMT 2023 , Edited by admin on Sat Dec 16 14:21:34 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
