Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H44O3 |
Molecular Weight | 416.6365 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3C[C@@H](O)C[C@H](O)C3)[C@H](C)\C=C\[C@H](C)C(C)(C)O
InChI
InChIKey=BPKAHTKRCLCHEA-UBFJEZKGSA-N
InChI=1S/C27H44O3/c1-18(8-9-19(2)26(3,4)30)24-12-13-25-21(7-6-14-27(24,25)5)11-10-20-15-22(28)17-23(29)16-20/h8-11,18-19,22-25,28-30H,6-7,12-17H2,1-5H3/b9-8+,21-11+/t18-,19+,22-,23-,24-,25+,27-/m1/s1
Molecular Formula | C27H44O3 |
Molecular Weight | 416.6365 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15733015
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15733015
Paricalcitol (Zemplar) is a synthetic vitamin D(2) analogue that inhibits the secretion of parathyroid hormone (PTH) through binding to the vitamin D receptor. It is approved in the US and in most European nations for intravenous use in the prevention and treatment of secondary hyperparathyroidism associated with chronic renal failure in adult, and in the US paediatric, patients. Paricalcitol effectively reduced elevated serum PTH levels and was generally well tolerated in children and adults with secondary hyperparathyroidism associated with chronic renal failure. In well designed clinical trials, paricalcitol was as effective as calcitriol and as well tolerated in terms of the incidence of prolonged hypercalcaemia and/or elevated calcium-phosphorus product (Ca x P). Preclinical and in vitro studies have demonstrated that paricalcitol's biological actions are mediated through binding of the vitamin D receptor, 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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1977 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZEMPLAR Approved UseParicalcitol is a vitamin D analog indicated for the prevention and treatment of secondary hyperparathyroidism associated with Chronic kidney disease (CKD) Stages 3 and 4 (1.1). CKD Stage 5 in patients on hemodialysis (HD) or peritoneal dialysis (PD) (1.2). 1.1 Chronic Kidney Disease Stages 3 and 4 Paricalcitol capsules are indicated for the prevention and treatment of secondary hyperparathyroidism associated with Chronic Kidney Disease (CKD) Stages 3 and 4. 1.2 Chronic Kidney Disease Stage 5 Paricalcitol capsules are indicated for the prevention and treatment of secondary hyperparathyroidism associated with CKD Stage 5 in patients on hemodialysis (HD) or peritoneal dialysis (PD)., 1.1 Chronic Kidney Disease Stages 3 and 4 Paricalcitol capsules are indicated for the prevention and treatment of secondary hyperparathyroidism associated with Chronic Kidney Disease (CKD) Stages 3 and 4., 1.2 Chronic Kidney Disease Stage 5 Paricalcitol capsules are indicated for the prevention and treatment of secondary hyperparathyroidism associated with CKD Stage 5 in patients on hemodialysis (HD) or peritoneal dialysis (PD). Launch Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.12 ng/mL |
1 μg 1 times / day multiple, oral dose: 1 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
PARICALCITOL plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN |
|
0.11 ng/mL |
1 μg 1 times / day multiple, oral dose: 1 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
PARICALCITOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.63 ng × h/mL |
1 μg 1 times / day multiple, oral dose: 1 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
PARICALCITOL plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN |
|
2.42 ng × h/mL |
1 μg 1 times / day multiple, oral dose: 1 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
PARICALCITOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15 h |
1 μg 1 times / day multiple, oral dose: 1 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
PARICALCITOL plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN |
|
16.8 h |
1 μg 1 times / day multiple, oral dose: 1 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
PARICALCITOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.2% |
1 μg 1 times / day multiple, oral dose: 1 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
PARICALCITOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
16 ug 3 times / week steady, oral (starting) Dose: 16 ug, 3 times / week Route: oral Route: steady Dose: 16 ug, 3 times / week Sources: |
unhealthy, 13.9 years (range: 10-16 years) n = 18 Health Status: unhealthy Condition: stages 3 to 5 chronic kidney disease Age Group: 13.9 years (range: 10-16 years) Sex: M+F Population Size: 18 Sources: |
Other AEs: Hyperphosphatemia, Hypercalcemia... Other AEs: Hyperphosphatemia (2 patients) Sources: Hypercalcemia (3 patients) |
1 ug 1 times / day multiple, oral Dose: 1 ug, 1 times / day Route: oral Route: multiple Dose: 1 ug, 1 times / day Sources: |
unhealthy, 48.5 years n = 51 Health Status: unhealthy Age Group: 48.5 years Sex: M+F Population Size: 51 Sources: |
Disc. AE: Hypercalcemia... AEs leading to discontinuation/dose reduction: Hypercalcemia (29%) Sources: |
23 ug 1 times / week multiple, intravenous (starting) Dose: 23 ug, 1 times / week Route: intravenous Route: multiple Dose: 23 ug, 1 times / week Sources: |
unhealthy, 53 ± 17 years (range: 18–83 years) n = 40 Health Status: unhealthy Condition: Secondary Hyperparathyroidism Age Group: 53 ± 17 years (range: 18–83 years) Sex: M+F Population Size: 40 Sources: |
Disc. AE: Hyperphosphatemia, Hypercalcemia... AEs leading to discontinuation/dose reduction: Hyperphosphatemia (40%) Sources: Hypercalcemia (15%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hyperphosphatemia | 2 patients | 16 ug 3 times / week steady, oral (starting) Dose: 16 ug, 3 times / week Route: oral Route: steady Dose: 16 ug, 3 times / week Sources: |
unhealthy, 13.9 years (range: 10-16 years) n = 18 Health Status: unhealthy Condition: stages 3 to 5 chronic kidney disease Age Group: 13.9 years (range: 10-16 years) Sex: M+F Population Size: 18 Sources: |
Hypercalcemia | 3 patients | 16 ug 3 times / week steady, oral (starting) Dose: 16 ug, 3 times / week Route: oral Route: steady Dose: 16 ug, 3 times / week Sources: |
unhealthy, 13.9 years (range: 10-16 years) n = 18 Health Status: unhealthy Condition: stages 3 to 5 chronic kidney disease Age Group: 13.9 years (range: 10-16 years) Sex: M+F Population Size: 18 Sources: |
Hypercalcemia | 29% Disc. AE |
1 ug 1 times / day multiple, oral Dose: 1 ug, 1 times / day Route: oral Route: multiple Dose: 1 ug, 1 times / day Sources: |
unhealthy, 48.5 years n = 51 Health Status: unhealthy Age Group: 48.5 years Sex: M+F Population Size: 51 Sources: |
Hypercalcemia | 15% Disc. AE |
23 ug 1 times / week multiple, intravenous (starting) Dose: 23 ug, 1 times / week Route: intravenous Route: multiple Dose: 23 ug, 1 times / week Sources: |
unhealthy, 53 ± 17 years (range: 18–83 years) n = 40 Health Status: unhealthy Condition: Secondary Hyperparathyroidism Age Group: 53 ± 17 years (range: 18–83 years) Sex: M+F Population Size: 40 Sources: |
Hyperphosphatemia | 40% Disc. AE |
23 ug 1 times / week multiple, intravenous (starting) Dose: 23 ug, 1 times / week Route: intravenous Route: multiple Dose: 23 ug, 1 times / week Sources: |
unhealthy, 53 ± 17 years (range: 18–83 years) n = 40 Health Status: unhealthy Condition: Secondary Hyperparathyroidism Age Group: 53 ± 17 years (range: 18–83 years) Sex: M+F Population Size: 40 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
19nor-1,25-dihydroxyvitamin D2 specifically induces CYP3A9 in rat intestine more strongly than 1,25-dihydroxyvitamin D3 in vivo and in vitro. | 2006 May |
|
Elevated phosphorus modulates vitamin D receptor-mediated gene expression in human vascular smooth muscle cells. | 2007 Nov |
Sample Use Guides
ZEMPLAR® (paricalcitol) Capsules indicated for the prevention and treatment of secondary hyperparathyroidism in chronic kidney disease (CKD). Zemplar Capsules may be administered daily or three times a week. When dosing three times weekly, the dose should be administered no more frequently than every other day. The average weekly doses for both daily and three times a week dosage regimens are similar
Zemplar Capsules may be taken without regard to food. No dosing adjustment is required in patients with mild and moderate hepatic impairment. The initial dose of Zemplar Capsules for CKD Stage 3 and 4 patients is based on baseline intact parathyroid hormone (iPTH) levels: 1 mcg daily dose if iPTH levels ≤ 500 pg/mL, 2 mcg daily dose if iPTH levels > 500 pg/mL. Dosing must be individualized and based on serum or plasma iPTH levels, with monitoring of serum calcium and serum phosphorus. The initial dose of Zemplar Capsules for CKD Stage 5 in micrograms is based on a baseline iPTH level (pg/mL)/80. To minimize the risk of hypercalcemia patients should be treated only after
their baseline serum calcium has been adjusted to 9.5 mg/dL or lower.
ZEMPLAR® (paricalcitol) Injection indicated for the prevention and treatment of secondary hyperparathyroidism associated with chronic kidney disease(CKD) Stage 5. The currently accepted target range for iPTH levels in CKD Stage 5 patients is no more than 1.5 to 3
times the non-uremic upper limit of normal. The recommended initial dose of Zemplar is 0.04 mcg/kg to 0.1 mcg/kg (2.8 – 7 mcg) administered as a bolus dose no more frequently than every other day at any time during dialysis.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18525004
Paricalcitol (1 nM to 1 uM) inhibits the TNF-α–mediated RANTES expression in human tubular epithelial cells in vitro. Paricalcitol reduces the chemoattraction of tubular epithelial cells to splenocytes and THP-1 cells in vitro.
Substance Class |
Chemical
Created
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admin
on
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Fri Dec 15 15:53:27 GMT 2023
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Record UNII |
6702D36OG5
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Record Status |
Validated (UNII)
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N0000006996
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N0000175908
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C39713
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740
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N0000006996
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N0000006996
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FDA ORPHAN DRUG |
492815
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N0000006996
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H05BX02
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CHEMBL1200622
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2791
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PARICALCITOL
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Stage 5 CDK: IV PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Elimination: Healthy Subjects: IV PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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