Identification

Name
Paricalcitol
Accession Number
DB00910  (APRD01165)
Type
Small Molecule
Groups
Approved, Investigational
Description

Paricalcitol is a synthetic vitamin D analog. Paricalcitol has been used to reduce parathyroid hormone levels. Paricalcitol is indicated for the prevention and treatment of secondary hyperparathyroidism associated with chronic renal failure.

Structure
Thumb
Synonyms
  • 19-Nor-1alpha,25-dihydroxyvitamin D2
  • Paricalcitol
External IDs
COMPOUND 49510
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ParicalcitolCapsule, liquid filled1 ug/1OralZydus Pharmaceuticals Usa, Inc.2010-06-14Not applicableUs
ParicalcitolInjection, solution2 ug/mLIntravenousAccord Healthcare Limited2016-03-01Not applicableUs
ParicalcitolInjection5 ug/mLIntravenousWest Ward Pharmaceutical2014-11-18Not applicableUs
ParicalcitolInjection, solution5 ug/mLIntravenousHospira, Inc.2014-11-01Not applicableUs
ParicalcitolInjection, solution5 ug/mLIntravenousAccord Healthcare Limited2016-03-01Not applicableUs
ParicalcitolCapsule, liquid filled2 ug/1OralZydus Pharmaceuticals Usa, Inc.2010-06-14Not applicableUs
ParicalcitolInjection2 ug/mLIntravenousWest Ward Pharmaceutical2014-11-18Not applicableUs
ParicalcitolInjection5 ug/mLIntravenousWest Ward Pharmaceutical2014-11-18Not applicableUs
ParicalcitolInjection, solution2 ug/mLIntravenousHospira, Inc.2014-11-01Not applicableUs
ZemplarInjection, solution5 ug/mLIntravenousAbbvie1998-04-17Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ParicalcitolCapsule, liquid filled4 ug/1OralGolden State Medical Supply2014-03-27Not applicableUs
ParicalcitolCapsule1 ug/1OralAmneal Pharmaceuticals2016-01-15Not applicableUs
ParicalcitolCapsule, gelatin coated4 ug/1OralRising Pharmaceuticals2015-11-03Not applicableUs
ParicalcitolInjection, solution5 ug/mLIntravenousDr Reddy's Laboratories2016-09-06Not applicableUs
ParicalcitolCapsule, liquid filled1 ug/1OralBanner Pharmacaps2014-03-27Not applicableUs
ParicalcitolCapsule, liquid filled2 ug/1OralAurobindo Pharma2016-01-14Not applicableUs
ParicalcitolInjection5 ug/mLIntravenousAmneal Biosciences2017-03-09Not applicableUs
ParicalcitolCapsule2 ug/1OralAlvogen, Inc.2016-03-012016-03-11Us
ParicalcitolCapsule1 ug/1OralGolden State Medical Supply2016-08-29Not applicableUs
ParicalcitolCapsule4 mg/1OralBanner Life Sciences Llc.2015-10-01Not applicableUs
International/Other Brands
Zemplar
Categories
UNII
6702D36OG5
CAS number
131918-61-1
Weight
Average: 416.6365
Monoisotopic: 416.329045274
Chemical Formula
C27H44O3
InChI Key
BPKAHTKRCLCHEA-UBFJEZKGSA-N
InChI
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
IUPAC Name
(1R,3R)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}cyclohexane-1,3-diol
SMILES

Pharmacology

Indication

For treatment of secondary hyperparathyroidism associated with chronic kidney disease (CKD) Stage 3 and 4

Structured Indications
Pharmacodynamics

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).

Mechanism of action

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.

TargetActionsOrganism
AVitamin D3 receptor
agonist
Human
Absorption

Well absorbed

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]
Protein binding

99.8% (bound to plasma proteins)

Metabolism

Metabolized by multiple hepatic and non-hepatic enzymes, including mitochondrial CYP24, as well as CYP3A4 and UGT1A4

Route of elimination

Paricalcitol is excreted primarily by hepatobiliary excretion.

Half life

4 to 6 hours

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]
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinParicalcitol may increase the arrhythmogenic activities of Acetyldigitoxin.Approved
AcetyldigoxinParicalcitol may increase the arrhythmogenic activities of Acetyldigoxin.Experimental
Aluminum hydroxideThe serum concentration of Aluminum hydroxide can be increased when it is combined with Paricalcitol.Approved
AmiodaroneThe serum concentration of Paricalcitol can be increased when it is combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Paricalcitol can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe serum concentration of Paricalcitol can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Paricalcitol can be decreased when combined with Atomoxetine.Approved
BendroflumethiazideBendroflumethiazide may increase the hypercalcemic activities of Paricalcitol.Approved
BoceprevirThe serum concentration of Paricalcitol can be increased when it is combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Paricalcitol can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Paricalcitol can be decreased when it is combined with Bosentan.Approved, Investigational
CalcidiolThe risk or severity of adverse effects can be increased when Paricalcitol is combined with Calcidiol.Approved, Nutraceutical
CalcipotriolThe risk or severity of adverse effects can be increased when Calcipotriol is combined with Paricalcitol.Approved
CalciumThe risk or severity of adverse effects can be increased when Calcium is combined with Paricalcitol.Nutraceutical
Calcium AcetateThe risk or severity of adverse effects can be increased when Calcium Acetate is combined with Paricalcitol.Approved
Calcium CarbonateThe risk or severity of adverse effects can be increased when Calcium Carbonate is combined with Paricalcitol.Approved
Calcium CitrateThe risk or severity of adverse effects can be increased when Calcium Citrate is combined with Paricalcitol.Approved
Calcium glubionateThe risk or severity of adverse effects can be increased when Calcium glubionate is combined with Paricalcitol.Approved
Calcium GluceptateThe risk or severity of adverse effects can be increased when Calcium Gluceptate is combined with Paricalcitol.Approved
Calcium gluconateThe risk or severity of adverse effects can be increased when Calcium gluconate is combined with Paricalcitol.Approved, Vet Approved
Calcium lactateThe risk or severity of adverse effects can be increased when Calcium lactate is combined with Paricalcitol.Approved, Experimental, Vet Approved
Calcium lactate gluconateThe risk or severity of adverse effects can be increased when Calcium lactate gluconate is combined with Paricalcitol.Experimental
Calcium laevulateThe risk or severity of adverse effects can be increased when Calcium laevulate is combined with Paricalcitol.Experimental
Calcium pangamateThe risk or severity of adverse effects can be increased when Calcium pangamate is combined with Paricalcitol.Experimental
Calcium PhosphateThe risk or severity of adverse effects can be increased when Calcium Phosphate is combined with Paricalcitol.Approved
CarbamazepineThe metabolism of Paricalcitol can be increased when combined with Carbamazepine.Approved, Investigational
CaseinThe risk or severity of adverse effects can be increased when Casein is combined with Paricalcitol.Approved
CeritinibThe serum concentration of Paricalcitol can be increased when it is combined with Ceritinib.Approved
ChlorothiazideChlorothiazide may increase the hypercalcemic activities of Paricalcitol.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypercalcemic activities of Paricalcitol.Approved
CholestyramineThe serum concentration of Paricalcitol can be decreased when it is combined with Cholestyramine.Approved
ClarithromycinThe serum concentration of Paricalcitol can be increased when it is combined with Clarithromycin.Approved
ClemastineThe metabolism of Paricalcitol can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Paricalcitol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Paricalcitol can be increased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Paricalcitol can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Paricalcitol can be decreased when it is combined with Colestipol.Approved
ConivaptanThe serum concentration of Paricalcitol can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Paricalcitol can be decreased when combined with Crizotinib.Approved
CyclopenthiazideCyclopenthiazide may increase the hypercalcemic activities of Paricalcitol.Experimental
CyclosporineThe metabolism of Paricalcitol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinParicalcitol may increase the arrhythmogenic activities of Cymarin.Experimental
DabrafenibThe serum concentration of Paricalcitol can be decreased when it is combined with Dabrafenib.Approved
DanazolDanazol may increase the hypercalcemic activities of Paricalcitol.Approved
DarunavirThe serum concentration of Paricalcitol can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Paricalcitol can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Paricalcitol can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Paricalcitol can be decreased when combined with Delavirdine.Approved
DeslanosideParicalcitol may increase the arrhythmogenic activities of Deslanoside.Approved
DigitoxinParicalcitol may increase the arrhythmogenic activities of Digitoxin.Approved
DigoxinThe risk or severity of adverse effects can be increased when Paricalcitol is combined with Digoxin.Approved
DihydroergotamineThe metabolism of Paricalcitol can be decreased when combined with Dihydroergotamine.Approved
DihydrotachysterolThe risk or severity of adverse effects can be increased when Paricalcitol is combined with Dihydrotachysterol.Approved
DiltiazemThe metabolism of Paricalcitol can be decreased when combined with Diltiazem.Approved
DoxercalciferolThe risk or severity of adverse effects can be increased when Doxercalciferol is combined with Paricalcitol.Approved
DoxycyclineThe metabolism of Paricalcitol can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Paricalcitol can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Paricalcitol can be decreased when it is combined with Enzalutamide.Approved
ErgocalciferolThe risk or severity of adverse effects can be increased when Paricalcitol is combined with Ergocalciferol.Approved, Nutraceutical
ErythromycinThe metabolism of Paricalcitol can be decreased when combined with Erythromycin.Approved, Vet Approved
FluconazoleThe metabolism of Paricalcitol can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Paricalcitol can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Paricalcitol can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Paricalcitol can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Paricalcitol can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Paricalcitol can be increased when it is combined with Fusidic Acid.Approved
GitoformateParicalcitol may increase the arrhythmogenic activities of Gitoformate.Experimental
HydrochlorothiazideHydrochlorothiazide may increase the hypercalcemic activities of Paricalcitol.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypercalcemic activities of Paricalcitol.Approved
ImatinibThe metabolism of Paricalcitol can be decreased when combined with Imatinib.Approved
IndapamideIndapamide may increase the hypercalcemic activities of Paricalcitol.Approved
IndinavirThe serum concentration of Paricalcitol can be increased when it is combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Paricalcitol can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Paricalcitol can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Paricalcitol can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Paricalcitol can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Paricalcitol can be increased when it is combined with Ketoconazole.Approved, Investigational
Lanatoside CParicalcitol may increase the arrhythmogenic activities of Lanatoside C.Experimental
LopinavirThe serum concentration of Paricalcitol can be increased when it is combined with Lopinavir.Approved
LovastatinThe metabolism of Paricalcitol can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Paricalcitol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Paricalcitol can be increased when combined with Lumacaftor.Approved
MethyclothiazideMethyclothiazide may increase the hypercalcemic activities of Paricalcitol.Approved
MetildigoxinParicalcitol may increase the arrhythmogenic activities of Metildigoxin.Experimental
MetolazoneMetolazone may increase the hypercalcemic activities of Paricalcitol.Approved
MifepristoneThe serum concentration of Paricalcitol can be increased when it is combined with Mifepristone.Approved, Investigational
Mineral oilThe serum concentration of Paricalcitol can be decreased when it is combined with Mineral oil.Approved, Vet Approved
MitotaneThe serum concentration of Paricalcitol can be decreased when it is combined with Mitotane.Approved
NefazodoneThe serum concentration of Paricalcitol can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Paricalcitol can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Paricalcitol can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Paricalcitol can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Paricalcitol can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Paricalcitol can be decreased when combined with Olaparib.Approved
OleandrinParicalcitol may increase the arrhythmogenic activities of Oleandrin.Experimental
OrlistatThe serum concentration of Paricalcitol can be decreased when it is combined with Orlistat.Approved, Investigational
OsimertinibThe serum concentration of Paricalcitol can be increased when it is combined with Osimertinib.Approved
OuabainParicalcitol may increase the arrhythmogenic activities of Ouabain.Approved
PalbociclibThe serum concentration of Paricalcitol can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Paricalcitol can be increased when combined with Pentobarbital.Approved, Vet Approved
PeruvosideParicalcitol may increase the arrhythmogenic activities of Peruvoside.Experimental
PhenobarbitalThe metabolism of Paricalcitol can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Paricalcitol can be increased when combined with Phenytoin.Approved, Vet Approved
PolythiazidePolythiazide may increase the hypercalcemic activities of Paricalcitol.Approved
PosaconazoleThe serum concentration of Paricalcitol can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Paricalcitol can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinParicalcitol may increase the arrhythmogenic activities of Proscillaridin.Experimental
QuinethazoneQuinethazone may increase the hypercalcemic activities of Paricalcitol.Approved
RanolazineThe metabolism of Paricalcitol can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Paricalcitol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Paricalcitol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Paricalcitol can be increased when combined with Rifapentine.Approved
RitonavirThe serum concentration of Paricalcitol can be increased when it is combined with Ritonavir.Approved, Investigational
SaquinavirThe serum concentration of Paricalcitol can be increased when it is combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Paricalcitol can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Paricalcitol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Paricalcitol can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Paricalcitol can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Paricalcitol can be increased when it is combined with Stiripentol.Approved
SucralfateThe serum concentration of Sucralfate can be increased when it is combined with Paricalcitol.Approved
SulfisoxazoleThe metabolism of Paricalcitol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe serum concentration of Paricalcitol can be increased when it is combined with Telaprevir.Withdrawn
TelithromycinThe serum concentration of Paricalcitol can be increased when it is combined with Telithromycin.Approved
TiclopidineThe metabolism of Paricalcitol can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Paricalcitol can be decreased when it is combined with Tocilizumab.Approved
TrichlormethiazideTrichlormethiazide may increase the hypercalcemic activities of Paricalcitol.Approved, Vet Approved
VenlafaxineThe metabolism of Paricalcitol can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Paricalcitol can be decreased when combined with Verapamil.Approved
VoriconazoleThe serum concentration of Paricalcitol can be increased when it is combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Paricalcitol can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

Synthesis Reference

Anchel Schwartz, Alexei Ploutno, Koby Wolfman, "Preparation of paricalcitol." U.S. Patent US20070149489, issued June 28, 2007.

US20070149489
General References
Not Available
External Links
Human Metabolome Database
HMDB15046
KEGG Drug
D00930
KEGG Compound
C08127
PubChem Compound
5281104
PubChem Substance
46505780
ChemSpider
4444552
ChEBI
7931
ChEMBL
CHEMBL1200622
Therapeutic Targets Database
DAP000211
PharmGKB
PA450798
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
ATC Codes
H05BX02 — Paricalcitol
AHFS Codes
  • 88:16.00
PDB Entries
Not Available
FDA label
Download (447 KB)
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCancer, Breast1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1RecruitingTreatmentMalignant Neoplasm of Pancreas1
1TerminatedTreatmentMucinous Adenocarcinoma of the Rectum / Stage IIA Rectal Cancer / Stage IIB Rectal Cancer / Stage IIC Rectal Cancer / Stage IIIB Rectal Cancer / Stage IIIC Rectal Cancer1
1TerminatedTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
2CompletedNot AvailableChronic Kidney Disease (CKD)1
2CompletedDiagnosticHypersensitivity1
2CompletedPreventionCardiovascular Disease (CVD) / End Stage Renal Disease (ESRD) / Hemodialysis-dependent patients / Inflammatory Responses1
2CompletedTreatmentChronic Kidney Disease (CKD)2
2CompletedTreatmentChronic Kidney Disease (CKD) / Diabetic Nephropathies1
2CompletedTreatmentChronic Kidney Disease on Hemodialysis / Hyperparathyroidism, Secondary1
2CompletedTreatmentHyperparathyroidism, Secondary / Transplant, Kidney1
2CompletedTreatmentHemodialysis-dependent patients / Hyperparathyroidism, Secondary2
2CompletedTreatmentHypocalcemia1
2CompletedTreatmentType 2 Diabetes Mellitus1
2RecruitingTreatmentAdenocarcinoma of the Pancreas / Resectable Pancreatic Cancers / Unresectable Pancreatic Cancer1
2RecruitingTreatmentUntreated Metastatic Pancreatic Ductal Adenocarcinoma1
2TerminatedTreatmentMetastatic Cancers / Prostate Cancer1
2Unknown StatusTreatmentLeukemias / Myelodysplastic Syndromes1
2, 3CompletedTreatmentChronic Kidney Disease (CKD)1
3CompletedTreatmentAlbuminuria / Disorder of Transplanted Kidney / Proteinuria1
3CompletedTreatmentBypass, Gastric / Parathyroid Hormone1
3CompletedTreatmentChronic Kidney Disease (CKD)2
3CompletedTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D / Hyperparathyroidism, Secondary1
3CompletedTreatmentChronic Kidney Disease (CKD) / Left Ventricular Hypertrophy1
3CompletedTreatmentChronic Kidney Disease Stage 3 and 41
3CompletedTreatmentEnd Stage Renal Disease (ESRD)1
3CompletedTreatmentEnd-Stage Renal Disease (ESRD) / Hyperparathyroidism, Secondary1
3CompletedTreatmentHemodialysis-dependent patients / Hyperparathyroidism, Secondary1
3CompletedTreatmentHyperparathyroidism / Hypophosphatemia, Familial1
3CompletedTreatmentKidney Diseases1
3CompletedTreatmentProteinuria1
3CompletedTreatmentRenal Insufficiency,Chronic3
3TerminatedTreatmentChronic Kidney Disease (CKD) Stage 5 / Left Ventricular Hypertrophy1
3TerminatedTreatmentChronic Kidney Disease (CKD) / Coronary Artery Disease / Hyperparathyroidism, Secondary / Hypovitaminosis D1
3WithdrawnTreatmentIgA Nephropathy1
4Active Not RecruitingTreatmentEndstage Renal Disease / Hyperparathyroidism, Secondary1
4CompletedPreventionChronic Kidney Disease (CKD)1
4CompletedPreventionChronic Kidney Disease (CKD) / Coronary Calcification / Deficiency, Vitamin D / Disorders of Calcium and Bone Metabolism1
4CompletedPreventionRenal Failure1
4CompletedTreatmentAnemias / Chronic Kidney Disease (CKD)1
4CompletedTreatmentCardiorenal Syndrome / Chronic Allograft Nephropathy (CAN)1
4CompletedTreatmentCardiovascular Disease (CVD) / Diabetic Nephropathies1
4CompletedTreatmentChronic Kidney Disease (CKD) / Hyperparathyroidism, Secondary3
4CompletedTreatmentChronic Kidney Disease (CKD) / Hemodialysis-dependent patients / Hyperparathyroidism, Secondary1
4CompletedTreatmentChronic Kidney Disease, Stage 5 / Hyperparathyroidism, Secondary1
4CompletedTreatmentDialysis therapy / Hyperparathyroidism, Secondary1
4CompletedTreatmentEnd Stage Renal Disease (ESRD) / Hyperparathyroidism, Secondary1
4CompletedTreatmentHemodialysis-dependent patients / Hypercalcemia / Hyperparathyroidism, Secondary / Parathyroid Hormone / Renal Insufficiency,Chronic1
4CompletedTreatmentHyperparathyroidism, Secondary4
4CompletedTreatmentKidney Failure,Chronic1
4CompletedTreatmentModerate to Severe Secondary Hyperparathyroidism / Stage 5 Chronic Kidney Diseases1
4CompletedTreatmentSecondary Hyperparathyroidism Due to Renal Causes1
4RecruitingTreatmentAnemias1
4TerminatedTreatmentDialysis therapy / Hyperparathyroidism, Secondary1
4TerminatedTreatmentEnd-Stage Kidney Disease1
4TerminatedTreatmentHypercalcemia / Hyperparathyroidism, Secondary / Hyperphosphataemia / Renal Failure1
4TerminatedTreatmentRenal Dysfunction1
Not AvailableActive Not RecruitingTreatmentOf the Pancreas / Previously Untreated Resectable Adenocarcinoma of the Pancreas / Subjects Must Have Previously Untreated Apparently Resectable Adenocarcinoma1
Not AvailableCompletedNot AvailableChronic Kidney Disease (CKD)1
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD)1
Not AvailableCompletedTreatmentChronic Kidney Disease (CKD) / Endothelial Dysfunction / Hypertensive / Inflammatory Reaction1
Not AvailableCompletedTreatmentFabry's Disease / Proteinuria1
Not AvailableCompletedTreatmentHyperparathyroidism, Secondary / Renal Disease, End Stage / Transplant; Failure, Kidney1
Not AvailableCompletedTreatmentHyperparathyroidism / Kidney Diseases1
Not AvailableRecruitingNot AvailableAlport Syndrome / Familial Benign Hematuria / Hereditary Kidney Disease / Pediatric Kidney Disease / Thin Basement Membrane Disease1
Not AvailableTerminatedNot AvailableEnd-Stage Renal Disease (ESRD) / Hyperparathyroidism, Secondary1
Not AvailableTerminatedTreatmentChronic Kidney Disease (CKD) / Deficiency, Vitamin D / Hyperparathyroidism, Secondary1
Not AvailableUnknown StatusDiagnosticChronic Kidney Disease (CKD) / Type 2 Diabetes Mellitus1
Not AvailableWithdrawnTreatmentHeart Failure, Unspecified1
Not AvailableWithdrawnTreatmentProteinuric Renal Disease1

Pharmacoeconomics

Manufacturers
  • Abbott laboratories pharmaceutical products div
  • Abbott laboratories
Packagers
Dosage forms
FormRouteStrength
CapsuleOral1 ug/1
CapsuleOral1 mg/1
CapsuleOral2 ug/1
CapsuleOral2 mg/1
CapsuleOral4 ug/1
CapsuleOral4 mg/1
Capsule, gelatin coatedOral1 ug/1
Capsule, gelatin coatedOral2 ug/1
Capsule, gelatin coatedOral4 ug/1
Capsule, liquid filledOral1 ug/1
Capsule, liquid filledOral2 ug/1
Capsule, liquid filledOral4 ug/1
InjectionIntravenous10 ug/2mL
InjectionIntravenous2 ug/mL
InjectionIntravenous5 ug/mL
Injection, solutionIntravenous2 ug/mL
Injection, solutionIntravenous5 ug/mL
SolutionIntravenous5 mcg
Prices
Unit descriptionCostUnit
Zemplar 4 mcg capsule37.58USD capsule
Zemplar 5 mcg/ml vial28.03USD ml
Zemplar 2 mcg capsule18.79USD capsule
Zemplar 2 mcg/ml vial11.22USD ml
Zemplar 1 mcg capsule9.39USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5246925 No1995-04-172012-04-17Us
US5597815 Yes1996-01-132016-01-13Us
US6361758 Yes1998-10-082018-10-08Us
US6136799 Yes1998-10-082018-10-08Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0068 mg/mLALOGPS
logP5.27ALOGPS
logP4.26ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.81ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.95 m3·mol-1ChemAxon
Polarizability51.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.795
Caco-2 permeable+0.776
P-glycoprotein substrateSubstrate0.7667
P-glycoprotein inhibitor INon-inhibitor0.7431
P-glycoprotein inhibitor IINon-inhibitor0.8491
Renal organic cation transporterNon-inhibitor0.8292
CYP450 2C9 substrateNon-substrate0.7968
CYP450 2D6 substrateNon-substrate0.8903
CYP450 3A4 substrateSubstrate0.7662
CYP450 1A2 substrateNon-inhibitor0.8127
CYP450 2C9 inhibitorNon-inhibitor0.8277
CYP450 2D6 inhibitorNon-inhibitor0.948
CYP450 2C19 inhibitorNon-inhibitor0.8491
CYP450 3A4 inhibitorNon-inhibitor0.8409
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6631
Ames testNon AMES toxic0.9116
CarcinogenicityNon-carcinogens0.9111
BiodegradationNot ready biodegradable0.988
Rat acute toxicity4.4277 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9069
hERG inhibition (predictor II)Non-inhibitor0.8015
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Vitamin D and derivatives
Direct Parent
Vitamin D and derivatives
Alternative Parents
Triterpenoids / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Triterpenoid / Tertiary alcohol / Cyclic alcohol / Secondary alcohol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol / Aliphatic homopolycyclic compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
seco-cholestane, hydroxy seco-steroid (CHEBI:7931 ) / Vitamin D2 and derivatives (C08127 ) / C27 bile acids, alcohols, and derivatives (LMST04030163 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Andress DL: Vitamin D treatment in chronic kidney disease. Semin Dial. 2005 Jul-Aug;18(4):315-21. [PubMed:16076355 ]
  4. Brancaccio D, Cozzolino M, Pasho S, Fallabrino G, Olivi L, Gallieni M: New acquisitions in therapy of secondary hyperparathyroidism in chronic kidney disease and peritoneal dialysis patients: role of vitamin D receptor activators. Contrib Nephrol. 2009;163:219-26. doi: 10.1159/000223802. Epub 2009 Jun 3. [PubMed:19494617 ]
  5. Wu-Wong JR, Nakane M, Gagne GD, Brooks KA, Noonan WT: Comparison of the pharmacological effects of paricalcitol and doxercalciferol on the factors involved in mineral homeostasis. Int J Endocrinol. 2010;2010:621687. doi: 10.1155/2010/621687. Epub 2010 Mar 2. [PubMed:20204178 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity
Specific Function
Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can...
Gene Name
CYP24A1
Uniprot ID
Q07973
Uniprot Name
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
Molecular Weight
58874.695 Da
References
  1. Robinson DM, Scott LJ: Paricalcitol: a review of its use in the management of secondary hyperparathyroidism. Drugs. 2005;65(4):559-76. [PubMed:15733015 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A4
Uniprot ID
P22310
Uniprot Name
UDP-glucuronosyltransferase 1-4
Molecular Weight
60024.535 Da

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:48