Details of the Drug

General Information of Drug (ID: DMCX0K3)

Drug Name

Cinacalcet

Synonyms

Cinacalcet [INN]; AMG 073; AMG073; Cinacalcet (USAN); Mimpara (TN); Sensipar (TN); N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine; N-[(1R)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine; N-((1R)-1-(1-Naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine; N-((1R)-1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine; (R)-N-(1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine; (R)-alpha-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethane amine

Indication

Disease Entry	ICD 11	Status	REF
Hyperparathyroidism	5A51	Approved	[1]
Kidney disease	GC2Z	Phase 3	[1]

Therapeutic Class

Calcimimetics

Affected Organisms

Humans and other mammals

ATC Code

H05BX01: Cinacalcet

H05BX: Other anti-parathyroid agents

H05B: ANTI-PARATHYROID AGENTS

H05: CALCIUM HOMEOSTASIS

H: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

357.4

Logarithm of the Partition Coefficient (xlogp)

6.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is rapidly absorbed following oral administration []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 18.3 mL/min/kg [3]
Elimination: 0.1% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 30 - 40 hours [3]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 7.19437 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.05% [3]
Vd: The volume of distribution (Vd) of drug is 1000 L []
Water Solubility: The ability of drug to dissolve in water is measured as 0.1 mg/mL [2]

Chemical Identifiers

Formula: C22H22F3N
IUPAC Name: N-[(1R)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine
Canonical SMILES: C[C@H](C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F
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
InChIKey: VDHAWDNDOKGFTD-MRXNPFEDSA-N

Cross-matching ID

PubChem CID: 156419
ChEBI ID: CHEMBL48390
CAS Number: 226256-56-0
UNII: UAZ6V7728S
DrugBank ID: DB01012
TTD ID: D03YGR
INTEDE ID: DR0326
ACDINA ID: D00131

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Extracellular calcium-sensing receptor (CASR)	TTBUYHA	CASR_HUMAN	Agonist	[5]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[6]
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[6]
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[7]

Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Hyperparathyroidism

ICD Disease Classification

5A51

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Extracellular calcium-sensing receptor (CASR)	DTT	CASR	5.81E-02	-0.03	-0.19
Cytochrome P450 1A2 (CYP1A2)	DME	CYP1A2	8.12E-01	3.88E-03	1.91E-02
Cytochrome P450 2D6 (CYP2D6)	DME	CYP2D6	4.26E-01	5.09E-02	2.01E-01
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	4.73E-01	-1.99E-02	-1.18E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Cinacalcet

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Etelcalcetide	DMHP9BL	Major	Increased risk of hypocalcemia by the combination of Cinacalcet and Etelcalcetide.	Hyper-parathyroidism [5A51]	[8]

Coadministration of a Drug Treating the Disease Different from Cinacalcet (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Oliceridine	DM6MDCF	Major	Decreased metabolism of Cinacalcet caused by Oliceridine mediated inhibition of CYP450 enzyme.	Acute pain [MG31]	[9]
Dronedarone	DMA8FS5	Moderate	Decreased metabolism of Cinacalcet caused by Dronedarone mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[10]
Posaconazole	DMUL5EW	Moderate	Decreased metabolism of Cinacalcet caused by Posaconazole mediated inhibition of CYP450 enzyme.	Aspergillosis [1F20]	[11]
Desipramine	DMT2FDC	Moderate	Decreased metabolism of Cinacalcet caused by Desipramine mediated inhibition of CYP450 enzyme.	Attention deficit hyperactivity disorder [6A05]	[12]
Clarithromycin	DM4M1SG	Moderate	Decreased metabolism of Cinacalcet caused by Clarithromycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[11]
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Cinacalcet caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[11]
Pexidartinib	DMS2J0Z	Moderate	Increased metabolism of Cinacalcet caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[13]
Lapatinib	DM3BH1Y	Moderate	Decreased metabolism of Cinacalcet caused by Lapatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[14]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Cinacalcet caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[11]
Dihydrocodeine	DMB0FWL	Moderate	Decreased metabolism of Cinacalcet caused by Dihydrocodeine mediated inhibition of CYP450 enzyme.	Chronic pain [MG30]	[12]
Nefazodone	DM4ZS8M	Moderate	Decreased metabolism of Cinacalcet caused by Nefazodone mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[11]
Vortioxetine	DM6F1PU	Major	Decreased metabolism of Cinacalcet caused by Vortioxetine mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[15]
OPC-34712	DMHG57U	Major	Decreased metabolism of Cinacalcet caused by OPC-34712 mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[16]
Clomipramine	DMINRKW	Moderate	Decreased metabolism of Cinacalcet caused by Clomipramine mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[12]
Doxepin	DMPI98T	Moderate	Decreased metabolism of Cinacalcet caused by Doxepin mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[12]
Tetrabenazine	DMYWQ0O	Major	Decreased metabolism of Cinacalcet caused by Tetrabenazine mediated inhibition of CYP450 enzyme.	Dissociative neurological symptom disorder [6B60]	[17]
Deutetrabenazine	DMUPFLI	Major	Decreased metabolism of Cinacalcet caused by Deutetrabenazine mediated inhibition of CYP450 enzyme.	Dystonic disorder [8A02]	[18]
Ingrezza	DMVPLNC	Major	Additive CNS depression effects by the combination of Cinacalcet and Ingrezza.	Dystonic disorder [8A02]	[19]
Tolterodine	DMSHPW8	Minor	Decreased metabolism of Cinacalcet caused by Tolterodine mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[20]
Itraconazole	DMCR1MV	Moderate	Decreased metabolism of Cinacalcet caused by Itraconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[11]
Miconazole	DMPMYE8	Moderate	Decreased metabolism of Cinacalcet caused by Miconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[11]
Ketoconazole	DMPZI3Q	Moderate	Decreased metabolism of Cinacalcet caused by Ketoconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[11]
Carvedilol	DMHTEAO	Moderate	Decreased metabolism of Cinacalcet caused by Carvedilol mediated inhibition of CYP450 enzyme.	Heart failure [BD10-BD1Z]	[12]
Boceprevir	DMBSHMF	Moderate	Decreased metabolism of Cinacalcet caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[11]
Telaprevir	DMMRV29	Moderate	Decreased metabolism of Cinacalcet caused by Telaprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[11]
Fosamprenavir	DM4W9B3	Moderate	Decreased metabolism of Cinacalcet caused by Fosamprenavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[11]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Cinacalcet caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[11]
Etravirine	DMGV8QU	Moderate	Increased metabolism of Cinacalcet caused by Etravirine mediated induction of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[21]
Atazanavir	DMSYRBX	Moderate	Decreased metabolism of Cinacalcet caused by Atazanavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[11]
Pirfenidone	DM6VZFQ	Moderate	Decreased metabolism of Cinacalcet caused by Pirfenidone mediated inhibition of CYP450 enzyme.	Idiopathic interstitial pneumonitis [CB03]	[8]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Decreased metabolism of Cinacalcet caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[8]
Brigatinib	DM7W94S	Moderate	Increased metabolism of Cinacalcet caused by Brigatinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[22]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Cinacalcet caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[23]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Cinacalcet caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[11]
Exjade	DMHPRWG	Moderate	Decreased metabolism of Cinacalcet caused by Exjade mediated inhibition of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[24]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Cinacalcet caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[8]
Dasatinib	DMJV2EK	Moderate	Decreased metabolism of Cinacalcet caused by Dasatinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[25]
Promethazine	DM6I5GR	Moderate	Decreased metabolism of Cinacalcet caused by Promethazine mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[12]
Metoclopramide	DMFA5MY	Moderate	Decreased metabolism of Cinacalcet caused by Metoclopramide mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[12]
Dexfenfluramine	DMJ7YDS	Moderate	Decreased metabolism of Cinacalcet caused by Dexfenfluramine mediated inhibition of CYP450 enzyme.	Obesity [5B80-5B81]	[12]
Methamphetamine	DMPM4SK	Moderate	Decreased metabolism of Cinacalcet caused by Methamphetamine mediated inhibition of CYP450 enzyme.	Pain [MG30-MG3Z]	[12]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Cinacalcet caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[26]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Cinacalcet caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[27]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Cinacalcet caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[11]
Levomepromazine	DMIKFEL	Moderate	Decreased metabolism of Cinacalcet caused by Levomepromazine mediated inhibition of CYP450 enzyme.	Psychotic disorder [6A20-6A25]	[12]
Aripiprazole	DM3NUMH	Moderate	Decreased metabolism of Cinacalcet caused by Aripiprazole mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[28]
Iloperidone	DM6AUFY	Major	Decreased metabolism of Cinacalcet caused by Iloperidone mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[29]
Pimozide	DMW83TP	Major	Decreased metabolism of Cinacalcet caused by Pimozide mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[30]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Cinacalcet caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[8]
Pitolisant	DM8RFNJ	Major	Decreased metabolism of Cinacalcet caused by Pitolisant mediated inhibition of CYP450 enzyme.	Somnolence [MG42]	[8]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Cinacalcet caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[31]
Trimeprazine	DMEMV9D	Moderate	Decreased metabolism of Cinacalcet caused by Trimeprazine mediated inhibition of CYP450 enzyme.	Vasomotor/allergic rhinitis [CA08]	[12]
Propafenone	DMPIBJK	Moderate	Decreased metabolism of Cinacalcet caused by Propafenone mediated inhibition of CYP450 enzyme.	Ventricular tachyarrhythmia [BC71]	[12]
Flecainide	DMSQDLE	Moderate	Decreased metabolism of Cinacalcet caused by Flecainide mediated inhibition of CYP450 enzyme.	Ventricular tachyarrhythmia [BC71]	[12]
Burosumab	DMKUOQV	Moderate	Increased risk of hypocalcemia by the combination of Cinacalcet and Burosumab.	Vitamin/non-protein cofactor absorption/transport disorder [5C63]	[32]


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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Crospovidone	E00626	Not Available	Disintegrant
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Cinacalcet 90 mg tablet	90 mg	Oral Tablet	Oral
Cinacalcet 30 mg tablet	30 mg	Oral Tablet	Oral
Cinacalcet 60 mg tablet	60 mg	Oral Tablet	Oral

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3308).
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Clinical pipeline report, company report or official report of Amgen (2009).
6	Clinical pharmacokinetic and pharmacodynamic profile of cinacalcet hydrochloride. Clin Pharmacokinet. 2009;48(5):303-11.
7	Effects of CYP3A inhibition on the metabolism of cilostazol. Clin Pharmacokinet. 1999;37 Suppl 2:61-8.
8	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
9	Product Information. Olinvyk (oliceridine). Trevena Inc, Chesterbrook, PA.
10	Product Information. Multaq (dronedarone). sanofi-aventis , Bridgewater, NJ.
11	Product Information. Sensipar (cinacalcet). Amgen USA, Thousand Oaks, CA.
12	Cerner Multum, Inc. "Australian Product Information.".
13	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
14	Product Information. Tykerb (lapatinib). Novartis Pharmaceuticals, East Hanover, NJ.
15	Product Information. Brintellix (vortioxetine). Takeda Pharmaceuticals America, Lincolnshire, IL.
16	Product Information. Rexulti (brexpiprazole). Otsuka American Pharmaceuticals Inc, Rockville, MD.
17	Product Information. Xenazine (tetrabenazine). Prestwick Pharmaceuticals Inc, Washington DC, VA.
18	Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA.
19	Product Information. Ingrezza (valbenazine). Neurocrine Biosciences, Inc., San Diego, CA.
20	Brynne N, Svanstrom C, AbergWistedt A, Hallen B, Bertilsson L "Fluoxetine inhibits the metabolism of tolterodin-pharmacokinetic implications and proposed clinical relevance." Br J Clin Pharmacol 48 (1999): 553-63. [PMID: 10583026]
21	Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
22	Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
23	Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
24	Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
25	Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ.
26	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
27	Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
28	Product Information. Abilify (aripiprazole). Bristol-Myers Squibb, Princeton, NJ.
29	Product Information. Fanapt (iloperidone). Vanda Pharmaceuticals Inc, Rockville, MD.
30	Canadian Pharmacists Association.
31	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
32	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".