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Compound Detail

CHEMBL232201

BENZIODARONE
💊 Approved Drug
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💊 Approved Drug
CCc1oc2ccccc2c1C(=O)c1cc(I)c(O)c(I)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL232201
Name BENZIODARONE
Phase Approved
Structure Type MOL
InChI Key CZCHIEJNWPNBDE-UHFFFAOYSA-N

Known Names

Amplivix Benciodarona Benziodarone L 2329 L-2329 NSC-82133
4
Targets
18
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names
1
Indications
1
Mechanisms

Molecular Properties

518.1
MW (Da)
5.14
ALogP
3
HBA
1
HBD
50.4
PSA (Ų)
0.39
QED
2
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn
USAN Stem -arone

Extended Properties

Molecular Formula C17H12I2O3
MW 518.09
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness 0.15

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Calmodulin inhibitor INHIBITOR Calmodulin-1 ✓ ✓

Indications

Cardiovascular Diseases

ATC Classification

C01DX04
benziodarone
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C01DX54
benziodarone, combinations
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Drug Warnings

Withdrawn
hepatotoxicity
Jaundice
Country: France; United Kingdom   Year: 1964
Withdrawn
hepatotoxicity
Jaundice
Country: France; United Kingdom   Year: 1964
Withdrawn
hepatotoxicity
Jaundice
Country: France; United Kingdom   Year: 1964

Activity Summary

IC50 14 meas. best 9.0
Kd 3 meas. best 7.11
EC50 1 meas. best 5.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.0 8.3678 1.0 9
Transthyretin
CHEMBL3194
 Kd 7.11 6.75 78.0 2
Eyes absent homolog 3
CHEMBL4296245
 IC50 5.47 5.47 3400.0 4
Transthyretin
CHEMBL3194
 IC50 5.35 5.35 4500.0 1
Baculoviral IAP repeat-containing protein 5
CHEMBL5989
 Kd 5.1 5.1 8000.0 1
Transthyretin
CHEMBL3194
 EC50 5.05 5.05 8900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 3.0 nM 8.52 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 3.0 nM 8.52 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 3.0 nM 8.52 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 3.0 nM 8.52 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Transthyretin Kd = 78.0 nM 7.11 Binding affinity to TTR V30M mutant (unknown origin) assessed as dissociation co... 38670538
Transthyretin Kd = 410.0 nM 6.39 Binding affinity to thyroxin binding site of TTR V30M mutant (unknown origin) ex... 37311373
Eyes absent homolog 3 IC50 = 3400.0 nM 5.47 Inhibition of human Eya3 isoform 2 (127 to 573 residues) incubated for 30 mins b... -
Eyes absent homolog 3 IC50 = 3400.0 nM 5.47 Inhibition Assay: The compounds were then tested using full-length human recombi... -
Eyes absent homolog 3 IC50 = 3400.0 nM 5.47 Inhibitory Assay: An inhibitory assay was conducted using the previously describ... -
Eyes absent homolog 3 IC50 = 3400.0 nM 5.47 Inhibition of poly-histidine and GST-tagged full length human Eya3 isoform 2 (12... -
Transthyretin IC50 = 4500.0 nM 5.35 Inhibition of acid mediated TTR V30M mutant aggregation (unknown origin) express... 37311373
Unchecked IC50 = 5854.7 nM 5.23 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Baculoviral IAP repeat-containing protein 5 Kd = 8000.0 nM 5.1 Binding affinity to human survivin expressed in Escherichia coli BL21 cells afte... 17391963
Transthyretin EC50 = 8900.0 nM 5.05 Binding affinity to TTR in human plasma assessed as target occupancy incubated f... 38670538

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1502
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37311373 10.1016/j.bmc.2023.117370 Transthyretin 7
38670538 10.1021/acs.jmedchem.3c02286 Transthyretin 5
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
27397500 10.1016/j.bmcl.2016.06.088 Cytochrome P450 2D6 1
27397500 10.1016/j.bmcl.2016.06.088 Cytochrome P450 2C9 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 Bile salt export pump 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 1
38670538 10.1021/acs.jmedchem.3c02286 Albumin 1

Data from ChEMBL 36 via Core Engine