U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PARICALCITOL

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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZEMPLAR

Approved Use

Paricalcitol 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 Date

1998
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
Hypercalcemia (3 patients)
Sources:
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%)
Hypercalcemia (15%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Paricalcitol versus calcitriol in the treatment of secondary hyperparathyroidism.
2003 Apr
Vitamin D treatment in chronic kidney disease.
2005 Jul-Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
19-Nor-1,25(OH)2D2 (a novel, noncalcemic vitamin D analogue), combined with arsenic trioxide, has potent antitumor activity against myeloid leukemia.
2005 Mar 15
Calcification inhibitors and Wnt signaling proteins are implicated in bovine artery smooth muscle cell calcification in the presence of phosphate and vitamin D sterols.
2006 Dec
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
Effects of paricalcitol and enalapril on atherosclerotic injury in mouse aortas.
2010
Preventing progression of cardiac hypertrophy and development of heart failure by paricalcitol therapy in rats.
2011 Sep 1
Synergistic induction of human cathelicidin antimicrobial peptide gene expression by vitamin D and stilbenoids.
2014 Mar
Patents

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
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.
Name Type Language
PARICALCITOL
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
PARICALCITOL [MART.]
Common Name English
PARICALCITOL [USP IMPURITY]
Common Name English
PARICALCITOL [MI]
Common Name English
(7E,22E)-19-NOR-9,10-SECOERGOSTA-5,7,22-TRIENE-1.ALPHA.,3.BETA.,25-TRIOL
Common Name English
COMPOUND 49510
Code English
PARICALCITOL [VANDF]
Common Name English
PARICALCITOL [USAN]
Common Name English
PARICALCITOL [USP-RS]
Common Name English
Paricalcitol [WHO-DD]
Common Name English
(1.ALPHA.3.BETA.,7E,22E)-19-NOR-9,10-SECOERGOSTA-5,7,22-TRIENE-1,3,25-TRIOL
Common Name English
PARICALCITOL [USP MONOGRAPH]
Common Name English
ZEMPLAR
Brand Name English
PARICALCITOL [ORANGE BOOK]
Common Name English
COMPOUND-49510
Code English
PARICALCITOL [HSDB]
Common Name English
PARICALCITOL [JAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000006996
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
WHO-VATC QH05BX02
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
NDF-RT N0000175908
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
NCI_THESAURUS C39713
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
LIVERTOX 740
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
NDF-RT N0000006996
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
NDF-RT N0000006996
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
FDA ORPHAN DRUG 492815
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
NDF-RT N0000006996
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
WHO-ATC H05BX02
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
Code System Code Type Description
FDA UNII
6702D36OG5
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PRIMARY
DRUG BANK
DB00910
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PRIMARY
HSDB
7360
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PRIMARY
EPA CompTox
DTXSID4048640
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PRIMARY
INN
7688
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PRIMARY
NCI_THESAURUS
C38693
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PRIMARY
USAN
JJ-08
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PRIMARY
PUBCHEM
5281104
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PRIMARY
RS_ITEM_NUM
1499403
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PRIMARY
SMS_ID
100000092510
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY
DRUG CENTRAL
2066
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY
CAS
131918-61-1
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY
MESH
C084656
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY
EVMPD
SUB09627MIG
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PRIMARY
CHEBI
7931
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PRIMARY
MERCK INDEX
m8413
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY Merck Index
DAILYMED
6702D36OG5
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY
RXCUI
73710
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1200622
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY
IUPHAR
2791
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
PRIMARY
WIKIPEDIA
PARICALCITOL
Created by admin on Fri Dec 15 15:53:27 GMT 2023 , Edited by admin on Fri Dec 15 15:53:27 GMT 2023
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