Compound Detail

CHEMBL388590

BENZBROMARONE

💊 Approved Drug

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💊 Approved Drug

CCc1oc2ccccc2c1C(=O)c1cc(Br)c(O)c(Br)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL388590
Name	BENZBROMARONE
Phase	Approved
Structure Type	MOL
InChI Key	WHQCHUCQKNIQEC-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Benzbromaron Benzbromarona Benzbromarone Benzpromarone Desuric L-2214 MJ 10061 MJ-10061 Narcaricin mite NSC-85433 Uroleap

Targets

103

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

424.1

MW (Da)

5.46

ALogP

HBA

HBD

50.4

PSA (Å²)

0.57

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Withdrawn
Chirality	Achiral

Routes of Administration

Oral

Flags

Withdrawn Natural Product

USAN Stem	-arone
USAN Year	1976

Extended Properties

Molecular Formula	C17H12Br2O3
MW	424.09
Aromatic Rings	3
Heavy Atoms	22
NP-Likeness	0.28

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Solute carrier family 22 member 12 inhibitor	INHIBITOR	Solute carrier family 22 member 12	✓	✓

Indications

Gout Familial Primary Pulmonary Hypertension Hyperuricemia

ATC Classification

M04AB03

benzbromarone

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIGOUT PREPARATIONS

Drug Warnings

Withdrawn

hepatotoxicity

Serious liver damage

Country: France; Portugal Year: 2003

Withdrawn

hepatotoxicity

Serious liver damage

Country: France; Portugal Year: 2003

Withdrawn

General Warning

Unfavourable benefit-risk evaluation

Country: France; Portugal Year: 2003

Activity Summary

IC50 84 meas. best 7.8

EC50 10 meas. best 7.23

Ki 7 meas. best 7.72

Kd 2 meas. best 6.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 2C9 CHEMBL3397	IC50	7.8	7.5267	16.0	3
Cytochrome P450 2C9 CHEMBL3397	Ki	7.72	7.72	19.0	3
Solute carrier family 22 member 12 CHEMBL6120	IC50	7.66	6.5938	22.0	16
Aldo-keto reductase family 1 member C1 CHEMBL5905	IC50	7.32	7.32	48.0	1
Unchecked CHEMBL612545	EC50	7.23	5.9167	59.0	3
Unchecked CHEMBL612545	IC50	6.98	6.2389	105.3	9
Staphylococcus aureus CHEMBL352	IC50	6.88	6.88	131.0	1
Multidrug resistance-associated protein 1 CHEMBL3004	Ki	6.72	6.72	190.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	6.7	6.585	200.0	2
Transthyretin CHEMBL3194	Kd	6.7	6.7	200.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.94	5.94	1148.0	1
Mitogen-activated protein kinase 14 CHEMBL260	IC50	5.91	5.91	1235.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.74	5.74	1804.0	1
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	5.71	5.71	1946.0	1
Candida albicans CHEMBL366	IC50	5.7	5.7	2000.0	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	IC50	5.68	5.68	2100.0	1
Solute carrier family 22 member 6 CHEMBL1641347	IC50	5.67	5.505	2120.0	2
Adenosine receptor A3 CHEMBL256	Ki	5.53	5.53	2952.0	1
ADMET CHEMBL612558	IC50	5.51	5.51	3100.0	2
Cytochrome P450 2C19 CHEMBL3622	Ki	5.43	5.43	3700.0	1
Multidrug resistance-associated protein 1 CHEMBL3004	IC50	5.4	5.4	4000.0	2
Cytochrome P450 2J2 CHEMBL3491	IC50	5.37	5.37	4260.0	1
Peroxisome proliferator-activated receptor gamma/Nuclear receptor corepressor 2 CHEMBL2096976	IC50	5.32	5.32	4811.0	1
Calpain-2 catalytic subunit CHEMBL4143	IC50	5.31	5.205	4879.6	2
Adenosine receptor A3 CHEMBL256	IC50	5.28	5.28	5222.0	1
Transthyretin CHEMBL3194	IC50	5.24	5.24	5700.0	1
Streptokinase A CHEMBL1293228	EC50	5.18	4.97	6550.0	2
Streptococcus sp. 'group A' CHEMBL612389	EC50	5.13	5.13	7439.0	1
Eyes absent homolog 3 CHEMBL4296245	IC50	5.08	4.8771	8300.0	7
Monocarboxylate transporter 2 CHEMBL2073718	IC50	5.05	5.05	9000.0	1
HSP60/HSP10 CHEMBL4106131	IC50	5.04	5.04	9100.0	1
Eyes absent homolog 2 CHEMBL1293275	IC50	4.99	4.99	10300.0	2
Eyes absent homolog 3 CHEMBL4296244	IC50	4.96	4.96	11000.0	3
Protein RecA CHEMBL1741171	EC50	4.94	4.94	11500.0	1
Envelope glycoprotein gp160 CHEMBL1293311	IC50	4.89	4.89	12800.0	1
Perilipin-1/ABHD5 CHEMBL3883313	IC50	4.82	4.82	14988.0	1
Bile salt export pump CHEMBL6020	IC50	4.8	4.7733	15900.0	3
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	4.77	4.77	17000.0	1
GroEL/GroES CHEMBL4106139	IC50	4.75	4.53	18000.0	2
Cytochrome P450 2C19 CHEMBL3622	IC50	4.74	4.74	18200.0	1
1-acylglycerol-3-phosphate O-acyltransferase ABHD5/Perilipin-5 CHEMBL3885501	IC50	4.73	4.73	18808.0	1
Monocarboxylate transporter 1 CHEMBL2073709	IC50	4.66	4.66	22000.0	1
Bile acid receptor CHEMBL2047	EC50	4.61	4.61	24500.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	4.54	4.54	29200.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	4.48	4.48	33100.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.41	4.41	39000.0	1
Influenza A virus CHEMBL613740	EC50	4.41	4.41	39000.0	1
ATP-binding cassette sub-family C member 2 CHEMBL5748	IC50	4.38	4.38	41600.0	1
Polymerase acidic protein CHEMBL1169598	Kd	4.32	4.32	48200.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	4.27	4.27	53800.0	4

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	19096.77	ng.hr.mL-1	Homo sapiens
AUC	95240.0	ng.hr.mL-1	Cebus
AUC	11072.72	ng.hr.mL-1	Rattus norvegicus
AUC	30657.98	ng.hr.mL-1	Rattus norvegicus
AUC	894108.95	ng.hr.mL-1	Sapajus apella
CL	3e-05	mL.min-1.g-1	Homo sapiens
CL	2e-06	mL.min-1.g-1	Homo sapiens
CL	0.032	uL/min	Homo sapiens
Cmax	4339.0	nM	Homo sapiens
Cmax	10422.32	nM	Rattus norvegicus
Cmax	10422.32	nM	Rattus norvegicus
Cmax	10021.46	nM	Rattus norvegicus
Cmax	34568.13	nM	Rattus norvegicus
F	36.11	%	Rattus norvegicus
MRT	3.48	hr	Rattus norvegicus
MRT	3.75	hr	Rattus norvegicus
T1/2	13.0	hr	Homo sapiens
T1/2	1.79	hr	Rattus norvegicus
T1/2	3.03	hr	Rattus norvegicus
Tmax	2.0	hr	Homo sapiens
Tmax	0.63	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
Cytochrome P450 2C9	IC50	=	16.0	nM	7.8	DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	-
Cytochrome P450 2C9	Ki	=	19.0	nM	7.72	Binding affinity to CYP2C9	18255300
Cytochrome P450 2C9	Ki	=	19.0	nM	7.72	Inhibition of CYP2C9	18211009
Cytochrome P450 2C9	Ki	=	19.0	nM	7.72	Inhibition of human CYP2C9	15615526
Solute carrier family 22 member 12	IC50	=	22.0	nM	7.66	Inhibition of URAT1 (unknown origin)	-
Solute carrier family 22 member 12	IC50	=	26.0	nM	7.58	Inhibition of human URAT1 expressed in xenopus oocyte assessed as inhibition of ...	21449597
Solute carrier family 22 member 12	IC50	=	35.0	nM	7.46	Inhibition of human URAT1 expressed in human MDCK cells	21449597
Solute carrier family 22 member 12	IC50	=	34.5	nM	7.46	Inhibition of URAT1 (unknown origin) transfected in dog MDCK cells assessed as i...	33062187
Cytochrome P450 2C9	IC50	=	41.0	nM	7.39	Inhibition of CYP2C9 (unknown origin)	33684442
Cytochrome P450 2C9	IC50	=	41.0	nM	7.39	Inhibition of CYP2C9 (unknown origin)	33062187
Solute carrier family 22 member 12	IC50	=	48.0	nM	7.32	Inhibition of URAT1 (unknown origin) by absorbance based assay	39108024
Aldo-keto reductase family 1 member C1	IC50	=	48.0	nM	7.32	Inhibition of 20-alpha HSD	19397269
Unchecked	EC50	=	59.0	nM	7.23	PUBCHEM_BIOASSAY: Fluorescence Cell-Based Retest of Candida albicans Growth in t...	-
Unchecked	IC50	=	105.3	nM	6.98	PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c...	-
Solute carrier family 22 member 12	IC50	=	120.0	nM	6.92	Inhibition of human URAT1 expressed in HEK293T cells assessed as reduction in [1...	28351592
Unchecked	IC50	=	130.0	nM	6.89	Inhibition of Staphylococcus aureus AgrC1	23294220
Staphylococcus aureus	IC50	=	131.0	nM	6.88	PUBCHEM_BIOASSAY: Inhibitors of Bacterial Quorum Sensing Structure Activity Rela...	-
Unchecked	IC50	=	131.2	nM	6.88	PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf...	-
Multidrug resistance-associated protein 1	Ki	=	190.0	nM	6.72	Inhibition of human MRP1 expressed in Spodoptera frugiperda Sf9 cells assessed a...	21530277
Solute carrier family 22 member 12	IC50	=	190.0	nM	6.72	Inhibition of human URAT1 expressed in Xenopus laevis oocytes assessed as inhibi...	33062187

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1401
-	10.5281/zenodo.13943903	ADMET	87
31158845	10.1038/s41586-019-1291-3	ADMET	70
36001935	10.1016/j.ejmech.2022.114682	ADMET	32
36634312	10.1021/acs.jnatprod.2c00531	Rattus norvegicus	13
28351592	10.1016/j.bmcl.2017.03.041	Solute carrier family 22 member 12	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
33062187	10.1021/acsmedchemlett.0c00176	Solute carrier family 22 member 12	5
37311373	10.1016/j.bmc.2023.117370	Transthyretin	5
28340987	10.1016/j.bmc.2016.10.022	NON-PROTEIN TARGET	5
30852084	10.1016/j.bmcl.2019.02.028	Unchecked	5
33062187	10.1021/acsmedchemlett.0c00176	ADMET	4
39108024	10.1021/acs.jmedchem.4c01480	Sapajus apella	4
30852084	10.1016/j.bmcl.2019.02.028	GroEL/GroES	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
33684442	10.1016/j.bmcl.2021.127900	ADMET	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
21449597	10.1021/jm1015022	Solute carrier family 22 member 12	3
36347120	10.1016/j.bmc.2022.117073	Solute carrier family 22 member 12	3

Data from ChEMBL 36 via Core Engine