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1. 19-nor-1,25-(oh)2d2
2. 19-nor-1alpha,25-dihydroxyvitamin D2
3. Paricalcitol-d6
4. Zemplar
1. 131918-61-1
2. Zemplar
3. Compound 49510
4. 19-nor-1alpha,25-dihydroxyvitamin D2
5. Paracalcin
6. Compound-49510
7. (1r,3r)-5-[(2e)-2-[(1r,3as,7ar)-1-[(e,2r,5s)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol
8. Chebi:7931
9. 6702d36og5
10. (1r,3r,7e)-17beta-[(2r,3e,5s)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-9,10-secoestra-5,7-diene-1,3-diol
11. Ncgc00182706-01
12. Paricalcitol [usan]
13. 19-nor-1,25-(oh)2d2
14. Zemplar (tn)
15. 19-nor-1-alpha,25-dihydroxyvitamin D2
16. Hsdb 7360
17. Paricalcitol [usan:usp:inn]
18. Unii-6702d36og5
19. Abt-358
20. (7e,22e)-19-nor-9,10-secoergosta-5,7,22-triene-1alpha,3beta,25-triol
21. Paricalcitol Solution
22. Paricalcitol [mi]
23. Paricalcitol [jan]
24. (1alpha.3beta,7e,22e)-19-nor-9,10-secoergosta-5,7,22-triene-1,3,25-triol
25. Paricalcitol [hsdb]
26. Schembl3655
27. Dsstox_cid_28566
28. Dsstox_rid_82838
29. Paricalcitol [vandf]
30. Dsstox_gsid_48640
31. Paricalcitol [mart.]
32. Bidd:gt0330
33. Paricalcitol [usp-rs]
34. Paricalcitol [who-dd]
35. Paricalcitol (jan/usp/inn)
36. Gtpl2791
37. Chembl1200622
38. Dtxsid4048640
39. Amy2878
40. Bdbm233195
41. Paricalcitol [orange Book]
42. Paricalcitol [usp Impurity]
43. Act07192
44. Ex-a4434
45. Paricalcitol [usp Monograph]
46. Tox21_112987
47. Lmst04030163
48. S6681
49. Zinc13911941
50. Akos005145562
51. Bcp9001050
52. Cs-0705
53. Db00910
54. 19-nor-9,10-secoergosta-5,7,22-triene-1,3,25-triol, (1alpha,3beta,7e,22e)-
55. (1r,3r)-5-(2-((1r,3as,7ar,e)-1-((2r,5s,e)-6-hydroxy-5,6-dimethylhept-3-en-2-yl)-7a-methyloctahydro-4h-inden-4-ylidene)ethylidene)cyclohexane-1,3-diol
56. Hy-50919
57. Cas-131918-61-1
58. C08127
59. D00930
60. 918p611
61. A937163
62. Q155746
63. (1.alpha.3.beta.,7e,22e)-19-nor-9,10-secoergosta-5,7,22-triene-1,3,25-triol
64. (7e,22e)-19-nor-9,10-secoergosta-5,7,22-triene-1.alpha.,3.beta.,25-triol
65. (1r,3r,5z)-5-[(2e)-2-[(1r,3as,7ar)-octahydro-1-[(1r,2e,4s)-5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4h-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol
66. 1,3-cyclohexanediol, 5-[(2e)-2-[(1r,3as,7ar)-octahydro-1-[(1r,2e,4s)-5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4h-inden-4-ylidene]ethylidene]-, (1r,3r,5z)-
| Molecular Weight | 416.6 g/mol |
|---|---|
| Molecular Formula | C27H44O3 |
| XLogP3 | 5 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 5 |
| Exact Mass | 416.32904526 g/mol |
| Monoisotopic Mass | 416.32904526 g/mol |
| Topological Polar Surface Area | 60.7 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 676 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 4 | |
|---|---|
| Drug Name | Paricalcitol |
| PubMed Health | Paricalcitol |
| Drug Classes | Antithyroid Agent |
| Drug Label | Paricalcitol, USP, the active ingredient in Zemplar Injection, is a synthetically manufactured analog of calcitriol, the metabolically active form of vitamin D indicated for the prevention and treatment of secondary hyperparathyroidism associated wit... |
| Active Ingredient | Paricalcitol |
| Dosage Form | Capsule; Injectable |
| Route | injection; Injection; Oral |
| Strength | 4mcg; 10mcg/ml; 0.04mcg/kg to 0.1mcg/kg; 5mcg/ml; 0.002mg/ml; 1mcg; 0.005mg/ml; 0.01mg/2ml (0.005mg/ml); 2mcg; 2mcg/ml |
| Market Status | Tentative Approval; Prescription |
| Company | Hospira; Sandoz Canada; Teva Pharms Usa; Banner Pharmacaps; Hikma; Rising Pharms; Dr Reddys Labs |
| 2 of 4 | |
|---|---|
| Drug Name | Zemplar |
| PubMed Health | Paricalcitol |
| Drug Classes | Antithyroid Agent |
| Drug Label | Paricalcitol, USP, the active ingredient in Zemplar Injection, is a synthetically manufactured analog of calcitriol, the metabolically active form of vitamin D indicated for the prevention and treatment of secondary hyperparathyroidism associated wit... |
| Active Ingredient | Paricalcitol |
| Dosage Form | Capsule; Injectable |
| Route | Injection; Oral |
| Strength | 4mcg; 1mcg; 0.002mg/ml; 0.005mg/ml; 2mcg |
| Market Status | Prescription |
| Company | Abbvie |
| 3 of 4 | |
|---|---|
| Drug Name | Paricalcitol |
| PubMed Health | Paricalcitol |
| Drug Classes | Antithyroid Agent |
| Drug Label | Paricalcitol, USP, the active ingredient in Zemplar Injection, is a synthetically manufactured analog of calcitriol, the metabolically active form of vitamin D indicated for the prevention and treatment of secondary hyperparathyroidism associated wit... |
| Active Ingredient | Paricalcitol |
| Dosage Form | Capsule; Injectable |
| Route | injection; Injection; Oral |
| Strength | 4mcg; 10mcg/ml; 0.04mcg/kg to 0.1mcg/kg; 5mcg/ml; 0.002mg/ml; 1mcg; 0.005mg/ml; 0.01mg/2ml (0.005mg/ml); 2mcg; 2mcg/ml |
| Market Status | Tentative Approval; Prescription |
| Company | Hospira; Sandoz Canada; Teva Pharms Usa; Banner Pharmacaps; Hikma; Rising Pharms; Dr Reddys Labs |
| 4 of 4 | |
|---|---|
| Drug Name | Zemplar |
| PubMed Health | Paricalcitol |
| Drug Classes | Antithyroid Agent |
| Drug Label | Paricalcitol, USP, the active ingredient in Zemplar Injection, is a synthetically manufactured analog of calcitriol, the metabolically active form of vitamin D indicated for the prevention and treatment of secondary hyperparathyroidism associated wit... |
| Active Ingredient | Paricalcitol |
| Dosage Form | Capsule; Injectable |
| Route | Injection; Oral |
| Strength | 4mcg; 1mcg; 0.002mg/ml; 0.005mg/ml; 2mcg |
| Market Status | Prescription |
| Company | Abbvie |
Paricalcitol is indicated for the prevention and treatment of secondary hyperparathyroidism associated with chronic kidney disease (CKD) Stage 3 and 4. /Included in US product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2966
Therapeutic doses of specific vitamin D analogs are used in the treatment of chronic hypocalcemia, hypophosphatemia, rickets, and osteodystrophy associated with various medical conditions including chronic renal failure, familial hypophosphatemia, and hypoparathyroidism (postsurgical or idiopathic, or pseudohypoparathyroidism). Some analogs have been found to reduct elevated parathyroid hormone concentrations in patients with renal osteodystrophy associated with hyperparathyroidism. Theoretically, any of the vitamin D analogs may be used for the above conditions, However, because of their pharmacologic properties, some may be more useful in certain situations than others. Alfacalcidol, calcitriol, and dihydrotachysterol are usually preferred in patients with renal failure since these patients have impaired ability to synthesize calcitriol from cholecalciferol and ergocalciferol; therefore, the response is more predictable. In addition, their shorter half-lives may make toxicity easier to manage (hypercalcemia reverses more quickly). Ergocalciferol may not be the preferred agent in the treatment of familial hypophosphatemia or hypoparathyroidism because the large doses needed are associated with a risk of overdose and hypercalcemia; dihydrotachysterol and calcitriol may be preferred. /Included in US product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2966
/Paricalcitol/ should not be given to patients with evidence of vitamin D toxicity, hypercalcemia, or hypersensitivity to any ingredient in this product.
Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 538
Doses of vitamin D analogs that do not exceed the physiologic requirement are usually nontoxic. However, some infants and patients with sarcoidosis or hypoparathyroidism may have increased sensitivity to vitamin D analogs. /Vitamin D analogs/
McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3541
Acute or chronic administration of excessive doses of vitamin D analogs or enhanced responsiveness to physiologic amounts of ergocalciferol or cholecalciferol may lead to hypervitaminosis D manifested by hypercalcemia. /Vitamin D analogs/
McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3541
Decreased renal function without hypercalcemia has also been reported in patients with hypoparathyroidism after long-term vitamin D analog therapy. Before therapy with vitamin D analogs is initiated, serum phosphate concentrations must be controlled. To avoid ectopic calcification, the serum calcium (in mg/dL) times phosphorus (in mg/dL) should not be allowed to exceed 70. Because administration of vitamin D analogs may increase phosphate absorption, patients with renal failure may require adjustment in the dosage of aluminum-containing antacids used to decrease phosphate absorption. /Vitamin D analogs/
McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3541
For more Drug Warnings (Complete) data for PARICALCITOL (8 total), please visit the HSDB record page.
For treatment of secondary hyperparathyroidism associated with chronic kidney disease (CKD) Stage 3 and 4
FDA Label
Secondary hyperparathyroidism is characterized by an elevation in parathyroid hormone (PTH) associated with inadequate levels of active vitamin D hormone. The source of vitamin D in the body is from synthesis in the skin and from dietary intake. Vitamin D requires two sequential hydroxylations in the liver and the kidney to bind to and to activate the vitamin D receptor (VDR). The endogenous VDR activator, calcitriol [1,25(OH)2 D3], is a hormone that binds to VDRs that are present in the parathyroid gland, intestine, kidney, and bone to maintain parathyroid function and calcium and phosphorus homeostasis, and to VDRs found in many other tissues, including prostate, endothelium and immune cells. VDR activation is essential for the proper formation and maintenance of normal bone. In the diseased kidney, the activation of vitamin D is diminished, resulting in a rise of PTH, subsequently leading to secondary hyperparathyroidism and disturbances in the calcium and phosphorus homeostasis.1 Decreased levels of 1,25(OH)2 D3 have been observed in early stages of chronic kidney disease. The decreased levels of 1,25(OH)2 D3 and resultant elevated PTH levels, both of which often precede abnormalities in serum calcium and phosphorus, affect bone turnover rate and may result in renal osteodystrophy. An in vitro study indicates that paricalcitol is not an inhibitor of CYP1A2, CYP2A6, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6, CYP2E1 or CYP3A at concentrations up to 50 nM (21 ng/mL).
H - Systemic hormonal preparations, excl. sex hormones and insulins
H05 - Calcium homeostasis
H05B - Anti-parathyroid agents
H05BX - Other anti-parathyroid agents
H05BX02 - Paricalcitol
Absorption
Well absorbed
Route of Elimination
Paricalcitol is excreted primarily by hepatobiliary excretion.
Volume of Distribution
30.8 7.5 L [CKD Stage 5-HD]
34.9 9.5 L [CKD Stage 5-PD]
23.8 L [healthy subjects]
Clearance
1.49 +/- 0.60 L/h [chronic kidney disease Stage 5 with hemodialysis]
1.54 +/- 0.95 L/h [chronic kidney disease Stage 5with peritoneal dialysis]
Stored mainly in liver and other fat depots. /Vitamin D and analogs/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2967
Many vitamin D analogs are readily absorbed from the GI tract following oral administration if fat absorption is normal. The presence of bile is required for absorption of ergocalciferol and the extent of GI absorption may be decreased in patients with hepatic, biliary, or GI disease (e.g., Crohn's disease, Whipple's disease, sprue). Because vitamin D is fat soluble, it is incorporated into chylomicrons and absorbed via the lymphatic system; approximately 80% of ingested vitamin D appears to be absorbed systemically through this mechanism, principally in the small intestine. Although some evidence suggested that intestinal absorption of vitamin D may be decreased in geriatric adults, other evidence did not show clinically important age-related alterations in GI absorption of the vitamin in therapeutic doses. It currently is not known whether aging alters the GI absorption of physiologic amounts of vitamin D. /Vitamin D analogs/
McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3543
It is not known whether paricalcitol ... is excreted in human milk.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2967
In healthy subjects, plasma radioactivity after a single 0.16 mg/kg intravenous bolus dose of 3H-paricalcitol (n=4) was attributed to parent drug. Paricalcitol was eliminated primarily by hepatobiliary excretion, as 74% of the radioactive dose was recovered in feces and only 16% was found in urine.
Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 538
For more Absorption, Distribution and Excretion (Complete) data for PARICALCITOL (7 total), please visit the HSDB record page.
Metabolized by multiple hepatic and non-hepatic enzymes, including mitochondrial CYP24, as well as CYP3A4 and UGT1A4
After oral administration of a 0.48 mcg/kg dose of 3 H-paricalcitol, parent drug was extensively metabolized, with only about 2% of the dose eliminated unchanged in the feces, and no parent drug found in the urine. Several metabolites were detected in both the urine and feces. Most of the systemic exposure was from the parent drug. Two minor metabolites, relative to paricalcitol, were detected in human plasma. One metabolite was identified as 24(R)-hydroxy paricalcitol, while the other metabolite was unidentified. The 24(R)-hydroxy paricalcitol is less active than paricalcitol in an in vivo rat model of PTH suppression.
Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 536
In vitro data suggest that paricalcitol is metabolized by multiple hepatic and non-hepatic enzymes, including mitochondrial CYP24, as well as CYP3A4 and UGT1A4. The identified metabolites include the product of 24(R)-hydroxylation, 24,26- and 24,28-dihydroxylation and direct glucuronidation.
Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 536
4 to 6 hours
In healthy subjects, the mean elimination half-life of paricalcitol is 4 to 6 hours over the studied dose range of 0.06 to 0.48 mcg/kg. The pharmacokinetics of paricalcitol capsule have been studied in patients with chronic kidney disease (CKD) Stage 3 and 4 patients. After administration of 4 mcg paricalcitol capsule in CKD Stage 3 patients, the mean elimination half-life of paricalcitol is 17 hours. The mean half-life of paricalcitol is 20 hours in CKD Stage 4 patients when given 3 mcg of paricalcitol capsule.
Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 536
Plasma half-life: 15 hours.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2967
Paricalcitol is a synthetic, biologically active vitamin D analog of calcitriol with modifications to the side chain (D2) and the A (19-nor) ring. Preclinical andin vitro studies have demonstrated that paricalcitol's biological actions are mediated through binding of the VDR, which results in the selective activation of vitamin D responsive pathways. Vitamin D and paricalcitol have been shown to reduce parathyroid hormone levels by inhibiting PTH synthesis and secretion.
Paricalcitol is a synthetic, biologically active vitamin D analog of calcitriol with modifications to the side chain (D2) and the A (19-nor) ring. Preclinical and in vitro studies have demonstrated that paricalcitol's biological actions are mediated through binding of the vitamin D receptor (VDR), which results in the selective activation of vitamin D responsive pathways. Vitamin D and paricalcitol have been shown to reduce parathyroid hormone levels by inhibiting PTH synthesis and secretion.
Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 536
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