Compound Detail

CHEMBL897

PROBENECID

💊 Approved Drug

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💊 Approved Drug

CCCN(CCC)S(=O)(=O)c1ccc(C(=O)O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL897
Name	PROBENECID
Phase	Approved
Structure Type	MOL
InChI Key	DBABZHXKTCFAPX-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Benemid Benuryl HC 5006 NSC-18786 P-(dipropylsulfamoyl)benzoic acid Probalan Probampicin Probecid Probenate Probenecid Probenecid component of col- Probenecid component of colbenemid +5 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

285.4

MW (Da)

2.20

ALogP

HBA

HBD

74.7

PSA (Å²)

0.83

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1951
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula	C13H19NO4S
MW	285.37
Aromatic Rings	1
Heavy Atoms	19
NP-Likeness	-1.32

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Solute carrier family 22 member 6 inhibitor	INHIBITOR	Solute carrier family 22 member 6	✓	✓
Solute carrier family 22 member 8 inhibitor	INHIBITOR	Organic anion transporter 3	✓	✓
Solute carrier family 22 member 11 inhibitor	INHIBITOR	Solute carrier family 22 member 11	✓	✓

Indications

Gout Cystitis, Hemorrhagic Infections Infertility, Male Obesity Urinary Tract Infections Cellulitis Heart Failure Heart Failure, Systolic Alcoholism Brain Injuries Diabetes Mellitus Diabetes Mellitus, Type 2 Influenza in Birds Kidney Diseases Neoplasms Chondrocalcinosis

ATC Classification

M04AB01

probenecid

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIGOUT PREPARATIONS

Activity Summary

Ki 38 meas. best 6.44

IC50 25 meas. best 5.52

EC50 1 meas.

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 9 CHEMBL3594	Ki	6.44	6.44	360.0	3
Carbonic anhydrase 2 CHEMBL205	Ki	6.37	6.37	431.0	3
Carbonic anhydrase 12 CHEMBL3242	Ki	5.91	5.91	1245.0	3
Organic anion transporter 3 CHEMBL2073672	IC50	5.52	5.52	3020.0	1
Solute carrier family 22 member 6 CHEMBL1641347	Ki	5.37	5.2167	4300.0	3
Organic anion transporter 3 CHEMBL1641348	Ki	5.36	4.98	4410.0	3
Organic anion transporter 3 CHEMBL2073666	Ki	5.35	5.025	4430.0	2
Organic anion transporter 3 CHEMBL1641348	IC50	5.31	5.18	4930.0	2
Organic anion transporter 3 CHEMBL2073666	IC50	5.22	5.22	6030.0	1
Solute carrier family 22 member 6 CHEMBL1641347	IC50	5.2	5.012	6300.0	5
Solute carrier family 22 member 6 CHEMBL5653	Ki	5.2	5.195	6309.6	2
Solute carrier family 22 member 20 CHEMBL5269	Ki	5.08	5.075	8400.0	2
Solute carrier family 22 member 12 CHEMBL6120	IC50	4.82	4.3933	15000.0	3
Solute carrier family 22 member 6 CHEMBL1777665	Ki	4.8	4.655	15800.0	2
Solute carrier family 22 member 11 CHEMBL2073677	IC50	4.59	4.425	25400.0	2
ATP-binding cassette sub-family C member 2 CHEMBL5748	Ki	4.38	4.38	42200.0	1
ATP-binding cassette sub-family C member 2 CHEMBL2073676	Ki	4.35	4.35	44600.0	1
Solute carrier family 22 member 11 CHEMBL2073677	Ki	4.35	4.305	44400.0	2
Solute carrier organic anion transporter family member 1A4 CHEMBL1781860	Ki	4.14	4.14	72900.0	1
Solute carrier organic anion transporter family member 1A1 CHEMBL1781859	Ki	4.13	4.13	74400.0	1
UDP-glucuronosyltransferase 1A7 CHEMBL1743317	Ki	4.02	4.02	96000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	0.25	mL.min-1.kg-1	Homo sapiens
CL	0.2	mL.min-1.kg-1	Homo sapiens
CL	0.25	mL.min-1.kg-1	Homo sapiens
CL	0.25	mL.min-1.kg-1	Homo sapiens
Cmax	123700.0	nM	Homo sapiens
F	80.0	%	Homo sapiens
Fu	0.13	-	Homo sapiens
Fu	0.13	-	Homo sapiens
MRT	8.7	hr	Homo sapiens
T1/2	5.9	hr	Homo sapiens
T1/2	4.0	hr	Homo sapiens
T1/2	0.27	hr	-
Tmax	1.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 9	Ki	=	360.0	nM	6.44	Inhibition of recombinant human carbonic anhydrase 9 after 15 mins by stopped fl...	25027802
Carbonic anhydrase 9	Ki	=	360.0	nM	6.44	Inhibition of human carbonic anhydrase 9 by stopped-flow CO2 hydrase assay	26007302
Carbonic anhydrase 9	Ki	=	360.0	nM	6.44	Inhibition of human carbonic anhydrase-9 incubated for 15 mins by stopped-flow C...	26264840
Carbonic anhydrase 2	Ki	=	431.0	nM	6.37	Inhibition of recombinant human carbonic anhydrase 2 after 15 mins by stopped fl...	25027802
Carbonic anhydrase 2	Ki	=	431.0	nM	6.37	Inhibition of human carbonic anhydrase 2 by stopped-flow CO2 hydrase assay	26007302
Carbonic anhydrase 2	Ki	=	431.0	nM	6.37	Inhibition of human carbonic anhydrase-2 incubated for 15 mins by stopped-flow C...	26264840
Carbonic anhydrase 12	Ki	=	1245.0	nM	5.91	Inhibition of human carbonic anhydrase-12 incubated for 15 mins by stopped-flow ...	26264840
Carbonic anhydrase 12	Ki	=	1245.0	nM	5.91	Inhibition of human carbonic anhydrase 12 by stopped-flow CO2 hydrase assay	26007302
Carbonic anhydrase 12	Ki	=	1245.0	nM	5.91	Inhibition of recombinant human carbonic anhydrase 12 after 15 mins by stopped f...	25027802
Organic anion transporter 3	IC50	=	3020.0	nM	5.52	Inhibition of mouse OAT3 expressed in CHO cells assessed as inhibition of fluore...	23344796
Solute carrier family 22 member 6	Ki	=	4300.0	nM	5.37	TP_TRANSPORTER: inhibition of PAH uptake in OAT1-expressing CHO cells	10929807
Solute carrier family 22 member 6	Ki	=	4410.0	nM	5.36	TP_TRANSPORTER: inhibition of Ochratoxin A uptake in OAT1-expressing S2 cells	11669456
Organic anion transporter 3	Ki	=	4410.0	nM	5.36	TP_TRANSPORTER: inhibition of Ochratoxin A uptake in OAT3-expressing S2 cells	11669456
Organic anion transporter 3	Ki	=	4430.0	nM	5.35	TP_TRANSPORTER: inhibition of PCG uptake in Oat3-expressing LLC-PK1 cells	11961115
Organic anion transporter 3	IC50	=	4930.0	nM	5.31	TP_TRANSPORTER: inhibition of ES uptake (ES: 50nM) in hOAT3-expressing S2 cells	14978359
Organic anion transporter 3	IC50	=	6030.0	nM	5.22	TP_TRANSPORTER: inhibition of ES uptake (ES: 50nM) in rOAT3-expressing S2 cells	14978359
Solute carrier family 22 member 6	IC50	=	6300.0	nM	5.2	TP_TRANSPORTER: inhibition of 6-Carboxyfluorescein uptake in OAT1-expressing CHO...	10929807
Solute carrier family 22 member 6	Ki	=	6309.57	nM	5.2	Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr	17553798
Solute carrier family 22 member 6	Ki	=	6400.0	nM	5.19	Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr	17553798
Solute carrier family 22 member 6	IC50	=	7400.0	nM	5.13	TP_TRANSPORTER: inhibition of Adefovir uptake in OAT1-expressing CHO cells	10991954

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	320
16472241	10.2174/1570163043334794	Hepatotoxicity	18
19364853	10.1128/aac.01689-08	Plasmodium falciparum	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
20070106	10.1021/jm901371v	Homo sapiens	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
23344796	10.1124/dmd.112.049569	Organic anion transporter 3	8
19725578	10.1021/jm900194w	Multidrug resistance-associated protein 1	6
30878828	10.1016/j.ejmech.2019.02.074	Transient receptor potential cation channel subfamily A member 1	5
18426954	10.1124/dmd.108.020479	ADMET	4
37703077	10.1021/acs.jmedchem.3c01116	Pannexin-1	4
7277396	10.1021/jm00139a020	Pan troglodytes	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
30769179	10.1016/j.ejmech.2019.01.043	ADMET	3
23344796	10.1124/dmd.112.049569	Solute carrier family 22 member 6	3
17553798	10.1074/jbc.m703467200	Solute carrier family 22 member 6	2
17325024	10.1124/dmd.106.012187	Solute carrier family 22 member 12	2
11880368	10.1074/jbc.m110918200	ATP-binding cassette sub-family C member 6	2

Data from ChEMBL 36 via Core Engine