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
| 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: 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 |
|||
| 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 |
|---|---|---|---|---|
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 |
|
| A prospective trial of phosphate and 1,25-dihydroxyvitamin D3 therapy in symptomatic adults with X-linked hypophosphatemic rickets. | 1992 Sep |
|
| Calcitriol directly sensitizes renal tubular cells to ATP-depletion- and iron-mediated attack. | 1999 Jun |
|
| All trans retinoic acid induces apoptosis in acute promyelocytic NB4 cells when combined with isoquinolinediol, a poly(ADP-ribose) polymerase inhibitor. | 2000 Apr |
|
| Vitamin K(2) inhibits adipogenesis, osteoclastogenesis, and ODF/RANK ligand expression in murine bone marrow cell cultures. | 2000 Dec |
|
| 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 |
|
| Regulation of vitamin D-1alpha-hydroxylase and -24-hydroxylase expression by dexamethasone in mouse kidney. | 2000 Mar |
|
| Carnosic acid and promotion of monocytic differentiation of HL60-G cells initiated by other agents. | 2001 Aug 15 |
|
| 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 |
|
| Mepe, the gene encoding a tumor-secreted protein in oncogenic hypophosphatemic osteomalacia, is expressed in bone. | 2001 Jun 15 |
|
| Failure of high doses of calcitriol and hypercalcaemia to induce apoptosis in hyperplastic parathyroid glands of azotaemic rats. | 2001 Mar |
|
| Apoptosis induction by 1alpha,25-dihydroxyvitamin D3 in prostate cancer. | 2002 Jul |
|
| Differentiation of murine melanocyte precursors induced by 1,25-dihydroxyvitamin D3 is associated with the stimulation of endothelin B receptor expression. | 2002 Sep |
|
| Effects of Seocalcitol (EB1089) on nitrosomethyl urea-induced rat mammary tumors. | 2003 Aug |
|
| 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 |
|
| Vitamin D enhances mitogenesis mediated by keratinocyte growth factor receptor in keratinocytes. | 2003 Jun 1 |
|
| Vitamin D inhibits G1 to S progression in LNCaP prostate cancer cells through p27Kip1 stabilization and Cdk2 mislocalization to the cytoplasm. | 2003 Nov 21 |
|
| Calcitriol-induced prostate-derived factor: autocrine control of prostate cancer cell growth. | 2004 Dec 20 |
|
| Gene expression analysis suggests that 1,25-dihydroxyvitamin D3 reverses experimental autoimmune encephalomyelitis by stimulating inflammatory cell apoptosis. | 2004 Jul 8 |
|
| Leptin corrects increased gene expression of renal 25-hydroxyvitamin D3-1 alpha-hydroxylase and -24-hydroxylase in leptin-deficient, ob/ob mice. | 2004 Mar |
|
| The functional consequences of cross-talk between the vitamin D receptor and ERK signaling pathways are cell-specific. | 2004 Nov 5 |
|
| Role of uncoupling protein 2 (UCP2) expression and 1alpha, 25-dihydroxyvitamin D3 in modulating adipocyte apoptosis. | 2004 Sep |
|
| 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 |
|
| Regulation of the human vitamin D3 receptor promoter in breast cancer cells is mediated through Sp1 sites. | 2005 Jan 31 |
|
| Regulation of renal calcium receptor gene expression by 1,25-dihydroxyvitamin D3 in genetic hypercalciuric stone-forming rats. | 2005 May |
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
| Substance Class |
Chemical
Created
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Edited
Sat Dec 16 14:21:34 GMT 2023
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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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4HF9ADM3YJ
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21764985
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