Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H44O3 |
Molecular Weight | 416.6365 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
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](O)C[C@H](O)C3=C)[C@H](C)CCCC(C)(C)O
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 | 416.6365 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
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.
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 |
---|---|---|---|---|
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 |
|
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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Potentiation of lipopolysaccharide-induced tumor necrosis factor-alpha expression by 1,25-dihydroxyvitamin D3. | 1992 Dec 1 |
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Hypercalcemia-induced renal insufficiency during therapy with dihydrotachysterol. | 1999 |
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Effectiveness of 1,25-dihydroxyvitamin D supplementation on blood pressure reduction in a pseudohypoparathyroidism patient with high renin activity. | 1999 Jan |
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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 |
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22-oxacalcitriol suppresses secondary hyperparathyroidism without inducing low bone turnover in dogs with renal failure. | 1999 Mar |
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A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review. | 2000 |
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Zinc increases the activity of vitamin D-dependent promoters in osteoblasts. | 2000 Apr 29 |
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Vitamin K(2) inhibits adipogenesis, osteoclastogenesis, and ODF/RANK ligand expression in murine bone marrow cell cultures. | 2000 Dec |
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Association of transforming growth factor beta1 genotype with therapeutic response to active vitamin D for postmenopausal osteoporosis. | 2000 Mar |
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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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24,25-dihydroxyvitamin D3 in combination with 1,25-dihydroxyvitamin D3 ameliorates renal osteodystrophy in rats with chronic renal failure. | 2000 May |
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Comparison of the relative effects of 1,24-dihydroxyvitamin D(2) [1, 24-(OH)(2)D(2)], 1,24-dihydroxyvitamin D(3) [1,24-(OH)(2)D(3)], and 1,25-dihydroxyvitamin D(3) [1,25-(OH)(2)D(3)] on selected vitamin D-regulated events in the rat. | 2000 Sep 1 |
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Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2). | 2001 |
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Beneficial effect of 1,25 dihydroxyvitamin D3 on cytokine-treated human pancreatic islets. | 2001 Apr |
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Transcriptional control of intestinal cytochrome P-4503A by 1alpha,25-dihydroxy vitamin D3. | 2001 Dec |
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1,25(OH)2 vitamin D3 induces elevated expression of the cell cycle-regulating genes P21 and P27 in squamous carcinoma cell lines of the head and neck. | 2001 Jan |
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Mepe, the gene encoding a tumor-secreted protein in oncogenic hypophosphatemic osteomalacia, is expressed in bone. | 2001 Jun 15 |
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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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Dietary phosphorus deprivation induces 25-hydroxyvitamin D(3) 1alpha-hydroxylase gene expression. | 2001 May |
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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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Mediation of unusually high concentrations of 1,25-dihydroxyvitamin D in homozygous klotho mutant mice by increased expression of renal 1alpha-hydroxylase gene. | 2002 Feb |
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Apoptosis induction by 1alpha,25-dihydroxyvitamin D3 in prostate cancer. | 2002 Jul |
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Deletion of deoxyribonucleic acid binding domain of the vitamin D receptor abrogates genomic and nongenomic functions of vitamin D. | 2002 Jul |
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Does melatonin induce apoptosis in MCF-7 human breast cancer cells in vitro? | 2002 Mar |
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HL60 cells halted in G1 or S phase differentiate normally. | 2002 Nov 15 |
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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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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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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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Gene expression analysis suggests that 1,25-dihydroxyvitamin D3 reverses experimental autoimmune encephalomyelitis by stimulating inflammatory cell apoptosis. | 2004 Jul 8 |
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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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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 |
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Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative. | 2005 Jan |
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Type 2 iodothyronine selenodeiodinase is expressed throughout the mouse skeleton and in the MC3T3-E1 mouse osteoblastic cell line during differentiation. | 2005 Jan |
|
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 |
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Regulation of renal calcium receptor gene expression by 1,25-dihydroxyvitamin D3 in genetic hypercalciuric stone-forming rats. | 2005 May |
|
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.
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17965521
CYP3A4 mRNA expression in LS180 cells treated with 100 nM of Calcitriol for 6 and 24 h was approximately 80- and 500-fold higher than the control.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:16:38 UTC 2023
by
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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
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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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100000092790
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CALCITRIOL
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17823
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M2917
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DB00136
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1086301
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D002117
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DTXSID5022722
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4393
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CHEMBL846
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FXC9231JVH
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466
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C330
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3482
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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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METABOLIC ENZYME -> SUBSTRATE |
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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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SOLVATE->ANHYDROUS |
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DERIVATIVE -> PARENT |
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
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PRODRUG -> 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 |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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