Identification

Name
Cinacalcet
Accession Number
DB01012
Description

Cinacalcet is a calcimimetic sold by Amgen under the trade name Sensipar® in North America and Australia and as Mimpara® in Europe. It is used to treat hyperparathyroidism due to parathyroid tumours or renal failure.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 357.412
Monoisotopic: 357.170434324
Chemical Formula
C22H22F3N
Synonyms
  • (R)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethane amine
  • Cinacalcet
  • CNC
  • N-((1R)-1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine
External IDs
  • AMG 073
  • AMG-073
  • AMG073
  • KRN-1493
  • KRN1493

Pharmacology

Indication

For the treatment of secondary hyperparathyroidism in patients with Chronic Kidney Disease who are on hemodialysis or peritoneal dialysis. Also for the treatment of hypercalcemia in patients with parathyroid carcinoma.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Cinacalcet is a drug that acts as a calcimimetic (i.e. it mimics the action of calcium on tissues). Secondary hyperparathyroidism (HPT) in patients with chronic kidney disease (CKD) is a progressive disease, associated with increases in parathyroid hormone (PTH) levels and derangements in calcium and phosphorus metabolism. Increased PTH stimulates osteoclastic activity resulting in cortical bone resorption and marrow fibrosis. The goals of treatment of secondary hyperparathyroidism are to lower levels of PTH, calcium, and phosphorus in the blood, in order to prevent progressive bone disease and the systemic consequences of disordered mineral metabolism. In CKD patients on dialysis with uncontrolled secondary HPT, reductions in PTH are associated with a favorable impact on bone-specific alkaline phosphatase (BALP), bone turnover and bone fibrosis. Cinacalcet reduces calcium levels by increasing the sensitivity of the calcium sensing receptor to extracellular calcium.

Mechanism of action

Cinacalcet directly lowers parathyroid hormone levels by increasing the sensitivity of the calcium sensing receptors to activation by extracellular calcium, resulting in the inhibition of PTH secretion. The reduction in PTH is associated with a concomitant decrease in serum calcium levels.

TargetActionsOrganism
AExtracellular calcium-sensing receptor
agonist
Humans
Absorption

Rapidly absorbed following oral administration.

Volume of distribution
  • 1000 L
Protein binding

Approximately 93 to 97% bound to plasma proteins.

Metabolism

Metabolism is hepatic by multiple enzymes, primarily CYP3A4, CYP2D6, and CYP1A2. After administration of a 75 mg radiolabeled dose to healthy volunteers, cinacalcet was rapidly and extensively metabolized via: 1) oxidative N-dealkylation to hydrocinnamic acid and hydroxy-hydrocinnamic acid, which are further metabolized via ß-oxidation and glycine conjugation; the oxidative N-dealkylation process also generates metabolites that contain the naphthalene ring; and 2) oxidation of the naphthalene ring on the parent drug to form dihydrodiols, which are further conjugated with glucuronic acid.

Hover over products below to view reaction partners

Route of elimination

Cinacalcet is metabolized by multiple enzymes, primarily CYP3A4, CYP2D6 and CYP1A2. Renal excretion of metabolites was the primary route of elimination of radioactivity.

Half-life

Terminal half-life is 30 to 40 hours. The mean half-life of cinacalcet is prolonged by 33% and 70% in patients with moderate and severe hepatic impairment, respectively.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Doses titrated up to 300 mg once daily have been safely administered to patients on dialysis. Overdosage of cinacalcet may lead to hypocalcemia.

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Cinacalcet can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Cinacalcet can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Cinacalcet can be increased when it is combined with Abiraterone.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Cinacalcet.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Cinacalcet.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Cinacalcet.
AcyclovirThe metabolism of Cinacalcet can be decreased when combined with Acyclovir.
AdalimumabThe metabolism of Cinacalcet can be increased when combined with Adalimumab.
AgomelatineThe metabolism of Agomelatine can be decreased when combined with Cinacalcet.
AlbendazoleThe metabolism of Cinacalcet can be decreased when combined with Albendazole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with food. Food markedly increases product bioavailability.

Products

Product Ingredients
IngredientUNIICASInChI Key
Cinacalcet hydrochloride1K860WSG25364782-34-3QANQWUQOEJZMLL-PKLMIRHRSA-N
Product Images
International/Other Brands
Mimpara
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CinacalcetTablet90 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
CinacalcetTablet60 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
CinacalcetTablet30 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
M-cinacalcetTabletOralMantra Pharma Inc2018-12-11Not applicableCanada
M-cinacalcetTabletOralMantra Pharma Inc2018-12-11Not applicableCanada
M-cinacalcetTabletOralMantra Pharma Inc2018-12-11Not applicableCanada
SensiparTablet, coated30 mg/1OralCarilion Materials Management2004-04-04Not applicableUs68151 474020180907 15195 1cscw1s
SensiparTablet, coated30 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs53808 057720180907 15195 1vuivdb
SensiparTablet, coated30 mg/1OralAMGEN INC2004-04-04Not applicableUs55513 0073 30 nlmimage10 1b1c8de4
SensiparTablet, coated30 mg/1OralA-S Medication Solutions2004-04-04Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-cinacalcetTabletOralApotex Corporation2016-05-20Not applicableCanada
Apo-cinacalcetTabletOralApotex Corporation2016-05-20Not applicableCanada
Apo-cinacalcetTabletOralApotex Corporation2016-05-20Not applicableCanada
Auro-cinacalcetTabletOralAuro Pharma Inc2019-02-01Not applicableCanada
Auro-cinacalcetTabletOralAuro Pharma Inc2019-02-01Not applicableCanada
Auro-cinacalcetTabletOralAuro Pharma Inc2019-02-01Not applicableCanada
CinacalcetTablet, film coated90 mg/1OralStrides Pharma Science Limited2019-08-22Not applicableUs
CinacalcetTablet90 mg/1OralExelan Pharmaceuticals Inc.2020-04-14Not applicableUs
CinacalcetTablet90 mg/1OralCipla USA Inc.2018-03-08Not applicableUs
CinacalcetTablet, film coated90 mg/1OralMylan Pharmaceuticals Inc.2019-05-23Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
H05BX01 — Cinacalcet
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Trifluoromethylbenzenes / Phenylpropylamines / Aralkylamines / Dialkylamines / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides
Substituents
Alkyl fluoride / Alkyl halide / Amine / Aralkylamine / Aromatic homopolycyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Naphthalene / Organic nitrogen compound / Organofluoride
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
secondary amino compound, naphthalenes, (trifluoromethyl)benzenes (CHEBI:48390)

Chemical Identifiers

UNII
UAZ6V7728S
CAS number
226256-56-0
InChI Key
VDHAWDNDOKGFTD-MRXNPFEDSA-N
InChI
InChI=1S/C22H22F3N/c1-16(20-13-5-10-18-9-2-3-12-21(18)20)26-14-6-8-17-7-4-11-19(15-17)22(23,24)25/h2-5,7,9-13,15-16,26H,6,8,14H2,1H3/t16-/m1/s1
IUPAC Name
[(1R)-1-(naphthalen-1-yl)ethyl]({3-[3-(trifluoromethyl)phenyl]propyl})amine
SMILES
C[C@@H](NCCCC1=CC(=CC=C1)C(F)(F)F)C1=CC=CC2=CC=CC=C12

References

Synthesis Reference

Revital Lifshitz-Liron, "Process for the preparation of cinacalcet base." U.S. Patent US20070259964, issued November 08, 2007.

US20070259964
General References
  1. Torres PU: Cinacalcet HCl: a novel treatment for secondary hyperparathyroidism caused by chronic kidney disease. J Ren Nutr. 2006 Jul;16(3):253-8. [PubMed:16825031]
  2. Padhi D, Harris R: Clinical pharmacokinetic and pharmacodynamic profile of cinacalcet hydrochloride. Clin Pharmacokinet. 2009;48(5):303-11. doi: 10.2165/00003088-200948050-00002. [PubMed:19566113]
  3. Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [PubMed:16368445]
Human Metabolome Database
HMDB0015147
KEGG Drug
D03504
PubChem Compound
156419
PubChem Substance
46506315
ChemSpider
137743
BindingDB
50416875
RxNav
407990
ChEBI
48390
ChEMBL
CHEMBL1201284
ZINC
ZINC000001550499
Therapeutic Targets Database
DAP000256
PharmGKB
PA164776671
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cinacalcet
AHFS Codes
  • 92:92.00 — Other Miscellaneous Therapeutic Agents
FDA label
Download (278 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentMale Osteoporosis1
4CompletedNot AvailableChronic Kidney Disease (CKD)1
4CompletedDiagnosticChronic Kidney Disease (CKD) / Hyperparathyroidism, Secondary / Kidney Diseases1
4CompletedDiagnosticParathyroid Hormone Suppression Test With Cinacalcet1
4CompletedTreatmentAnemia / Hyperparathyroidism, Secondary1
4CompletedTreatmentArterial Stiffness / Hyperparathyroidism1
4CompletedTreatmentCalcification / Calcifications, Vascular / Cardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Chronic Renal Failure (CRF) / Coronary Artery Calcifications / End Stage Renal Disease (ESRD) / Hyperparathyroidism / Hyperparathyroidism, Secondary / Kidney Diseases / Nephrology1
4CompletedTreatmentChronic Kidney Disease (CKD) / Hemodialysis Treatment / Hyperparathyroidism, Secondary1
4CompletedTreatmentChronic Kidney Disease (CKD) / Hyperparathyroidism, Secondary1
4CompletedTreatmentEnd Stage Renal Disease (ESRD)1

Pharmacoeconomics

Manufacturers
  • Amgen inc
Packagers
  • Amgen Inc.
  • Cardinal Health
  • Dept Health Central Pharmacy
  • Kaiser Foundation Hospital
  • Patheon Inc.
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
TabletOral
TabletOral30 mg/1
TabletOral60 mg/1
TabletOral90 mg/1
Tablet, film coatedOral30 mg/1
Tablet, film coatedOral60 mg/1
Tablet, film coatedOral90 mg/1
PowderNot applicable20 kg/20kg
Tablet, film coatedOral30 mg
Tablet, film coatedOral60 mg
Tablet, film coatedOral90 mg
TabletOral30 mg
TabletOral60 mg
TabletOral90 mg
Tablet, coatedOral30 mg/1
Tablet, coatedOral60 mg/1
Tablet, coatedOral90 mg/1
Prices
Unit descriptionCostUnit
Sensipar 90 mg tablet44.03USD tablet
Sensipar 60 mg tablet29.35USD tablet
Sensipar 30 mg tablet14.69USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2202879No2005-08-302015-10-23Canada
US6031003No2000-02-292016-12-14Us
US6211244No2001-04-032015-10-23Us
US7829595No2010-11-092026-09-22Us
US6011068No2000-01-042018-03-08Us
US6313146No2001-11-062016-12-14Us
US9375405No2016-06-282026-09-22Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySlightly soluble (in HCl salt form)Not Available
logP6.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.59e-05 mg/mLALOGPS
logP5.57ALOGPS
logP6.27ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)10.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.12 m3·mol-1ChemAxon
Polarizability37.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9927
Caco-2 permeable+0.7058
P-glycoprotein substrateSubstrate0.5309
P-glycoprotein inhibitor IInhibitor0.8512
P-glycoprotein inhibitor IIInhibitor0.6937
Renal organic cation transporterInhibitor0.5305
CYP450 2C9 substrateNon-substrate0.7761
CYP450 2D6 substrateSubstrate0.8293
CYP450 3A4 substrateNon-substrate0.5425
CYP450 1A2 substrateInhibitor0.9206
CYP450 2C9 inhibitorNon-inhibitor0.8572
CYP450 2D6 inhibitorInhibitor0.8188
CYP450 2C19 inhibitorInhibitor0.8795
CYP450 3A4 inhibitorInhibitor0.7166
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5904
Ames testNon AMES toxic0.5152
CarcinogenicityNon-carcinogens0.8785
BiodegradationNot ready biodegradable0.9932
Rat acute toxicity2.8511 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9175
hERG inhibition (predictor II)Inhibitor0.8494
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

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
Senses changes in the extracellular concentration of calcium ions. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system.
Gene Name
CASR
Uniprot ID
P41180
Uniprot Name
Extracellular calcium-sensing receptor
Molecular Weight
120672.385 Da
References
  1. de Francisco AL: Cinacalcet HCl: a novel therapeutic for hyperparathyroidism. Expert Opin Pharmacother. 2005 Mar;6(3):441-52. [PubMed:15794735]
  2. Rothe HM, Shapiro WB, Sun WY, Chou SY: Calcium-sensing receptor gene polymorphism Arg990Gly and its possible effect on response to cinacalcet HCl. Pharmacogenet Genomics. 2005 Jan;15(1):29-34. [PubMed:15864123]
  3. Tasic V: Management of renal osteodystrophy in children. Turk J Pediatr. 2005;47 Suppl:13-8. [PubMed:15884662]
  4. Moe SM, Cunningham J, Bommer J, Adler S, Rosansky SJ, Urena-Torres P, Albizem MB, Guo MD, Zani VJ, Goodman WG, Sprague SM: Long-term treatment of secondary hyperparathyroidism with the calcimimetic cinacalcet HCl. Nephrol Dial Transplant. 2005 Oct;20(10):2186-93. Epub 2005 Jul 19. [PubMed:16030053]
  5. Cunningham J: Management of secondary hyperparathyroidism. Ther Apher Dial. 2005 Aug;9 Suppl 1:S35-40. [PubMed:16109140]
  6. Eriguchi R, Umakoshi J, Tominaga Y, Sato Y: Successful treatment of inoperable recurrent secondary hyperparathyroidism with cinacalcet HCl. NDT Plus. 2008 Aug;1(4):218-220. Epub 2008 May 25. [PubMed:19461861]
  7. Belozeroff V, Goodman WG, Ren L, Kalantar-Zadeh K: Cinacalcet lowers serum alkaline phosphatase in maintenance hemodialysis patients. Clin J Am Soc Nephrol. 2009 Mar;4(3):673-9. doi: 10.2215/CJN.03790808. Epub 2009 Mar 4. [PubMed:19261825]
  8. Meola M, Petrucci I, Barsotti G: Long-term treatment with cinacalcet and conventional therapy reduces parathyroid hyperplasia in severe secondary hyperparathyroidism. Nephrol Dial Transplant. 2009 Mar;24(3):982-9. doi: 10.1093/ndt/gfn654. Epub 2009 Jan 30. [PubMed:19181759]
  9. Drueke TB, Ritz E: Treatment of secondary hyperparathyroidism in CKD patients with cinacalcet and/or vitamin D derivatives. Clin J Am Soc Nephrol. 2009 Jan;4(1):234-41. doi: 10.2215/CJN.04520908. Epub 2008 Dec 3. [PubMed:19056615]
  10. 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
Humans
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
References
  1. Padhi D, Harris R: Clinical pharmacokinetic and pharmacodynamic profile of cinacalcet hydrochloride. Clin Pharmacokinet. 2009;48(5):303-11. doi: 10.2165/00003088-200948050-00002. [PubMed:19566113]
  2. Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [PubMed:16368445]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Padhi D, Harris R: Clinical pharmacokinetic and pharmacodynamic profile of cinacalcet hydrochloride. Clin Pharmacokinet. 2009;48(5):303-11. doi: 10.2165/00003088-200948050-00002. [PubMed:19566113]
  2. Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [PubMed:16368445]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Padhi D, Harris R: Clinical pharmacokinetic and pharmacodynamic profile of cinacalcet hydrochloride. Clin Pharmacokinet. 2009;48(5):303-11. doi: 10.2165/00003088-200948050-00002. [PubMed:19566113]
  2. Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [PubMed:16368445]
  3. Poon G: Cinacalcet hydrochloride (Sensipar). Proc (Bayl Univ Med Cent). 2005 Apr;18(2):181-4. [PubMed:16200170]
  4. Cinacalcet FDA label [File]

Drug created on June 13, 2005 07:24 / Updated on August 09, 2020 06:16

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