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Compound Detail

CHEMBL1201284

CINACALCET
💊 Approved Drug
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💊 Approved Drug
C[C@@H](NCCCc1cccc(C(F)(F)F)c1)c1cccc2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201284
Name CINACALCET
Phase Approved
Structure Type MOL
InChI Key VDHAWDNDOKGFTD-MRXNPFEDSA-N
Therapeutic ✓ Yes

Known Names

AMG 073 AMG-073 AMG073 Cinacalcet KRN-1493 KRN1493
7
Targets
9
Activities
2
Assay Types
8
PK Parameters
20
Publications
6
Known Names
9
Indications

Molecular Properties

357.4
MW (Da)
6.14
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.52
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -calcet
USAN Year 2002

Extended Properties

Molecular Formula C22H22F3N
MW 357.42
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -1.05

Indications

Parathyroid Diseases Hyperparathyroidism Hyperparathyroidism, Secondary Kidney Failure, Chronic Renal Insufficiency, Chronic Chronic Kidney Disease-Mineral and Bone Disorder Hyperparathyroidism, Primary Memory Disorders Rickets, Hypophosphatemic

ATC Classification

H05BX01
cinacalcet
Level 1: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
Level 2: CALCIUM HOMEOSTASIS

Activity Summary

IC50 5 meas. best 7.3
EC50 4 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Extracellular calcium-sensing receptor
CHEMBL1878
 EC50 8.4 7.75 4.0 2
Cytochrome P450 2D6
CHEMBL289
 IC50 7.3 7.3 50.0 2
Glycine receptor subunit alpha-1
CHEMBL5845
 EC50 6.5 6.5 320.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 5.53 5.53 2930.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.22 5.22 5990.0 1
Angiotensin-converting enzyme 2
CHEMBL3736
 IC50 4.55 4.55 28200.0 1
Unchecked
CHEMBL612545
 IC50 4.13 4.13 74000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 364.57 ng.hr.mL-1 Rattus norvegicus
AUC 679.1 ng.hr.mL-1 Rattus norvegicus
CL 44.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 270.0 nM Rattus norvegicus
Cmax 500.0 nM Rattus norvegicus
F 19.0 % Rattus norvegicus
T1/2 6.0 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Extracellular calcium-sensing receptor EC50 = 4.0 nM 8.4 Agonist activity at human CaSR expresssed in HEK293 cells in presence of glucose... 37442941
Cytochrome P450 2D6 IC50 = 50.0 nM 7.3 Inhibition Assay: Incubations were conducted in 96 well microtiter plates based ... -
Cytochrome P450 2D6 IC50 = 50.0 nM 7.3 Inhibition Assay: Incubations were conducted in 96 well microtiter plates based ... -
Extracellular calcium-sensing receptor EC50 = 80.0 nM 7.1 Positive allosteric modulation of human CaSR transfected in CHO cells after 5 hr... 23465611
Glycine receptor subunit alpha-1 EC50 = 320.0 nM 6.5 Potentiation of human GlyR-alpha1 expressed in Xenopus laevis oocytes assessed a... 25790278
SARS-CoV-2 EC50 = 2930.0 nM 5.53 Antiviral activity against SARS-CoV-2 infected in African green monkey Vero E6 c... 37659195
Replicase polyprotein 1ab IC50 = 5990.0 nM 5.22 Inhibition of SARS-CoV-2 3CL protease using DabcylKTSAVLQSGFRKME-Edans amide as ... 37659195
Angiotensin-converting enzyme 2 IC50 = 28200.0 nM 4.55 Inhibition of recombinant human ACE2 using MCA-Tyr-Val-Ala-Asp-Ala-Pro-Lys(DNP)-... 34812616
Unchecked IC50 = 74000.0 nM 4.13 Inhibition of porcine heart malate dehydrogenase preincubated for 5 min followed... 34812616

Literature References

PubMed DOI Target Context # Activities
- 10.1101/2024.03.28.586928 ADMET 100
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
37442941 10.1021/acs.jmedchem.3c00698 ADMET 11
37442941 10.1021/acs.jmedchem.3c00698 Rattus norvegicus 5
37442941 10.1021/acs.jmedchem.3c00698 Unchecked 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
34812616 10.1021/acs.jmedchem.1c01547 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
25790278 10.1021/jm501873p Glycine receptor subunit alpha-1 3
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 2

Data from ChEMBL 36 via Core Engine