Cinacalcet

Identification

Summary

Cinacalcet is a calcium sensing receptor agonist used to treat secondary hyperparathyroidism in chronic kidney disease and hypercalcemia in parathyroid carcinoma.

Brand Names

Mimpara, Sensipar

Generic Name

Cinacalcet

DrugBank Accession Number

DB01012

Background

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

Similar Structures

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

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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.

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Associated Conditions

Indication Type	Indication	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Hypercalcemia	••••••••••••	•••••	••••••• •••••••••••••••••••	••••••
Treatment of	Hypercalcemia	••••••••••••	•••••	••••••••••• •••••••••	••••••
Treatment of	Secondary hyperparathyroidism (shpt)	••••••••••••	•••••	••••••• •••••• ••••••• •••••• •••••••• •••••••	••••••

Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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.

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Cinacalcet
- Hydrocinnamic acid
- hydroxy-hydrocinnamic acid

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

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Toxicity

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

Pathways

Not Available

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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Drug	Interaction
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Abametapir	The serum concentration of Cinacalcet can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Cinacalcet can be increased when combined with Abatacept.
Abiraterone	The serum concentration of Cinacalcet can be increased when it is combined with Abiraterone.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Cinacalcet.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Cinacalcet.

Food Interactions

Take with food. Food markedly increases product bioavailability.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Cinacalcet hydrochloride	1K860WSG25	364782-34-3	QANQWUQOEJZMLL-PKLMIRHRSA-N

Product Images

International/Other Brands

Mimpara

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cinacalcet	Tablet	30 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable
Cinacalcet	Tablet	90 mg	Oral	Sanis Health Inc	Not applicable	Not applicable
Cinacalcet	Tablet	90 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable
Cinacalcet	Tablet	60 mg	Oral	Sanis Health Inc	Not applicable	Not applicable
Cinacalcet	Tablet	60 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-cinacalcet	Tablet	60 mg	Oral	Apotex Corporation	2016-05-20	Not applicable
Apo-cinacalcet	Tablet	30 mg	Oral	Apotex Corporation	2016-05-20	Not applicable
Apo-cinacalcet	Tablet	90 mg	Oral	Apotex Corporation	2016-05-20	Not applicable
Auro-cinacalcet	Tablet	30 mg	Oral	Auro Pharma Inc	2019-02-01	Not applicable
Auro-cinacalcet	Tablet	90 mg	Oral	Auro Pharma Inc	2019-02-01	Not applicable

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

Torres PU: Cinacalcet HCl: a novel treatment for secondary hyperparathyroidism caused by chronic kidney disease. J Ren Nutr. 2006 Jul;16(3):253-8. [Article]
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. [Article]
Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [Article]
FDA Approved Drug Products: SENSIPAR (cinacalcet) tablets [Link]

External Links

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
PDBe Ligand: YP4
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Cinacalcet

PDB Entries

7m3f / 8wpg / 8wpu

FDA label

Download (278 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Chronic Kidney Disease (CKD)	1
4	Completed	Diagnostic	Chronic Kidney Disease (CKD) / Kidney Diseases / Secondary Hyperparathyroidism (SHPT)	1
4	Completed	Diagnostic	Parathyroid Hormone Suppression Test With Cinacalcet	1
4	Completed	Supportive Care	Effect of Drugs	1
4	Completed	Treatment	Anemia / Secondary Hyperparathyroidism (SHPT)	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

Form	Route	Strength
Tablet	Oral	66.12 mg
Tablet	Oral	30.000 mg
Tablet	Oral	30 mg/1
Tablet	Oral	33.064 mg
Tablet	Oral	60 mg/1
Tablet	Oral	90 mg/1
Tablet, film coated	Oral	30 mg/1
Tablet, film coated	Oral	60 mg/1
Tablet, film coated	Oral	90 mg/1
Tablet, film coated	Oral
Powder	Not applicable	20 kg/20kg
Tablet, film coated	Oral	30 MG
Tablet, film coated	Oral	60 MG
Tablet, film coated	Oral	90 MG
Tablet, coated	Oral	3000000 mg
Tablet, coated	Oral	90 mg
Granule	Oral	1 MG
Granule	Oral	2.5 MG
Granule	Oral	5 MG
Tablet	Oral	1 mg
Tablet	Oral	2.5 mg
Tablet	Oral	5 mg
Tablet	Oral	90.000 mg
Tablet, coated	Oral	6000000 mg
Tablet	Oral
Tablet	Oral	30 mg
Tablet	Oral	60 mg
Tablet	Oral	90 mg
Tablet, coated	Oral	30 mg/1
Tablet, coated	Oral	60 mg/1
Tablet, coated	Oral	90 mg/1
Tablet, coated	Oral	60 mg
Tablet, coated	Oral	30 mg
Tablet, film coated	Oral	25 mg

Prices

Unit description	Cost	Unit
Sensipar 90 mg tablet	44.03USD	tablet
Sensipar 60 mg tablet	29.35USD	tablet
Sensipar 30 mg tablet	14.69USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
CA2202879	No	2005-08-30	2015-10-23
US6031003	No	2000-02-29	2016-12-14
US6211244	No	2001-04-03	2015-10-23
US7829595	No	2010-11-09	2026-09-22
US6011068	No	2000-01-04	2018-03-08
US6313146	No	2001-11-06	2016-12-14
US9375405	No	2016-06-28	2026-09-22

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	Slightly soluble (in HCl salt form)	Not Available
logP	6.5	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.59e-05 mg/mL	ALOGPS
logP	5.57	ALOGPS
logP	6.27	Chemaxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	10.01	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	1	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	12.03 Å²	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	100.12 m³·mol^-1	Chemaxon
Polarizability	37.9 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9927
Caco-2 permeable	+	0.7058
P-glycoprotein substrate	Substrate	0.5309
P-glycoprotein inhibitor I	Inhibitor	0.8512
P-glycoprotein inhibitor II	Inhibitor	0.6937
Renal organic cation transporter	Inhibitor	0.5305
CYP450 2C9 substrate	Non-substrate	0.7761
CYP450 2D6 substrate	Substrate	0.8293
CYP450 3A4 substrate	Non-substrate	0.5425
CYP450 1A2 substrate	Inhibitor	0.9206
CYP450 2C9 inhibitor	Non-inhibitor	0.8572
CYP450 2D6 inhibitor	Inhibitor	0.8188
CYP450 2C19 inhibitor	Inhibitor	0.8795
CYP450 3A4 inhibitor	Inhibitor	0.7166
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.5904
Ames test	Non AMES toxic	0.5152
Carcinogenicity	Non-carcinogens	0.8785
Biodegradation	Not ready biodegradable	0.9932
Rat acute toxicity	2.8511 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9175
hERG inhibition (predictor II)	Inhibitor	0.8494

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-1900000000-ff50504d0f6ffef59a7b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0009000000-30de3a35c06e2a4cd476
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0109000000-0f06d743b71ba9afe6b2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0659000000-052fb83cfa9b7a8ddfb4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1419000000-ea1cc2b109f130827c89
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0900000000-ee0697ef986f03240d06
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004j-1920000000-8cc62f64015e54be64d5
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	197.3458841	predicted	DarkChem Lite v0.1.0
[M-H]-	180.98474	predicted	DeepCCS 1.0 (2019)
[M+H]+	197.6766841	predicted	DarkChem Lite v0.1.0
[M+H]+	183.34274	predicted	DeepCCS 1.0 (2019)
[M+Na]+	197.8125841	predicted	DarkChem Lite v0.1.0
[M+Na]+	189.95772	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	80	N/A	N/A	A29290

Details1. Extracellular calcium-sensing receptor

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

de Francisco AL: Cinacalcet HCl: a novel therapeutic for hyperparathyroidism. Expert Opin Pharmacother. 2005 Mar;6(3):441-52. [Article]
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. [Article]
Tasic V: Management of renal osteodystrophy in children. Turk J Pediatr. 2005;47 Suppl:13-8. [Article]
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. [Article]
Cunningham J: Management of secondary hyperparathyroidism. Ther Apher Dial. 2005 Aug;9 Suppl 1:S35-40. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Details1. Cytochrome P450 3A4

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

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. [Article]
Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [Article]

Details2. Cytochrome P450 2D6

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

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. [Article]
Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [Article]
Flockhart Table of Drug Interactions [Link]

Details3. Cytochrome P450 1A2

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

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. [Article]
Dong BJ: Cinacalcet: An oral calcimimetic agent for the management of hyperparathyroidism. Clin Ther. 2005 Nov;27(11):1725-51. [Article]
Poon G: Cinacalcet hydrochloride (Sensipar). Proc (Bayl Univ Med Cent). 2005 Apr;18(2):181-4. [Article]
Cinacalcet FDA label [File]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Cinacalcet

Identification

Structure for Cinacalcet (DB01012)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

Enzymes

References

References

References