Compound Detail

CHEMBL35

FUROSEMIDE

💊 Approved Drug

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💊 Approved Drug

NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL35
Name	FUROSEMIDE
Phase	Approved
Structure Type	MOL
InChI Key	ZZUFCTLCJUWOSV-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Aluzine 20 Aluzine 40 Aluzine 500 Aquamed Diuresal Dryptal Froop Frumax Frumil Frusemide Frusetic Frusid +16 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

330.8

MW (Da)

1.89

ALogP

HBA

HBD

122.6

PSA (Å²)

0.77

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1966
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Stem	-semide
USAN Year	1964

Extended Properties

Molecular Formula	C12H11ClN2O5S
MW	330.75
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	-1.77

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Sodium-(potassium)-chloride cotransporter 2 inhibitor	INHIBITOR	Solute carrier family 12 member 1	✓	✓

Indications

Cardiovascular Diseases Fibrosis Heart Failure Heart Failure Hypertension Liver Cirrhosis Nephrotic Syndrome Pulmonary Edema Syndrome Atherosclerosis Bronchiolitis Coronary Disease Diabetes Mellitus, Type 2 Essential Hypertension Hypercholesterolemia Kidney Calculi Kidney Diseases Lung Diseases Myocardial Infarction Pre-Eclampsia

ATC Classification

C03CA01

furosemide

Level 1: CARDIOVASCULAR SYSTEM

Level 2: DIURETICS

Drug Warnings

Black Box Warning

General Warning

Country: United States

Activity Summary

Ki 18 meas. best 7.28

IC50 13 meas. best 7.1

Kd 3 meas. best 6.2

EC50 2 meas. best 5.21

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 14 CHEMBL3510	Ki	7.28	7.28	52.0	1
Carbonic anhydrase 1 CHEMBL261	Ki	7.21	7.21	62.0	1
Carbonic anhydrase 2 CHEMBL205	Ki	7.19	7.19	65.0	1
Carbonic anhydrase 1 CHEMBL261	IC50	7.1	7.1	80.0	1
Carbonic anhydrase 6 CHEMBL3025	Ki	6.61	6.61	245.0	1
Carbonic anhydrase 12 CHEMBL3242	Ki	6.58	6.58	261.0	1
Carbonic anhydrase 5B, mitochondrial CHEMBL3969	Ki	6.49	6.49	322.0	1
Carbonic anhydrase 9 CHEMBL3594	Ki	6.38	6.38	420.0	1
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	Ki	6.3	6.3	499.0	1
Carbonic anhydrase 7 CHEMBL2326	Ki	6.29	6.29	513.0	1
Carbonic anhydrase 13 CHEMBL2186	Ki	6.26	6.26	550.0	1
Carbonic anhydrase 4 CHEMBL3729	Ki	6.25	6.25	564.0	1
Carbonic anhydrase 2 CHEMBL205	Kd	6.2	5.85	630.0	2
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	Ki	5.64	5.64	2285.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.5	5.5	3200.0	1
G-protein coupled receptor 35 CHEMBL1293267	Ki	5.49	5.49	3270.0	1
11-beta-hydroxysteroid dehydrogenase 1 CHEMBL3910	IC50	5.42	5.42	3760.0	1
11-beta-hydroxysteroid dehydrogenase 1 CHEMBL4235	IC50	5.42	5.42	3760.0	1
G-protein coupled receptor 35 CHEMBL1293267	EC50	5.21	5.08	6200.0	2
Solute carrier family 22 member 6 CHEMBL1777665	Ki	5.02	5.02	9500.0	1
Aquaporin-4 CHEMBL5291512	IC50	5.0	5.0	10000.0	1
Felis catus CHEMBL612670	IC50	5.0	5.0	10000.0	1
Plasmodium falciparum CHEMBL364	IC50	4.9	4.8667	12589.2	3
Holo-[acyl-carrier-protein] synthase CHEMBL4734	IC50	4.9	4.9	12700.0	1
Hepatic sodium/bile acid cotransporter CHEMBL5287	IC50	4.82	4.82	15000.0	1
Solute carrier organic anion transporter family member 2A1 CHEMBL2073680	Ki	4.33	4.33	47000.0	1
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	Kd	4.28	4.28	53000.0	1
CDGSH iron-sulfur domain-containing protein 1 CHEMBL1795168	IC50	4.27	4.27	53460.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	0.59	mL.min-1.kg-1	Homo sapiens
CL	2.4	mL.min-1.kg-1	Homo sapiens
CL	2.4	mL.min-1.kg-1	Homo sapiens
CL	0.7	mL.min-1.kg-1	Homo sapiens
CL	-	-	Rattus norvegicus
CL	-	-	Rattus norvegicus
CL	1.6	mL.min-1.kg-1	Homo sapiens
CL	2.0	mL.min-1.kg-1	Homo sapiens
CL	2.9	mL.min-1.kg-1	Macaca
CL	4.8	mL.min-1.kg-1	Rattus norvegicus
CL	12.0	mL.min-1.kg-1	Canis lupus familiaris
CL	6.31	mL.min-1.g-1	Homo sapiens
CL	3.0	uL.min-1.(10^6cells)-1	Homo sapiens
CL	7.2e-05	mL.min-1.g-1	Homo sapiens
CL	-	-	Homo sapiens
CL	84.9	mL.min-1.kg-1	Homo sapiens
CL	0.99	uL.min-1.(10^6cells)-1	Homo sapiens
CL	2.12	mL.min-1.kg-1	Homo sapiens
CL	1.6	mL.min-1.kg-1	Homo sapiens
CL	1.7	mL.min-1.kg-1	Homo sapiens
CL	0.072	uL/min	Homo sapiens
Cmax	18100.0	nM	Homo sapiens
F	79.0	%	Homo sapiens
F	40.0	%	Homo sapiens
F	64.0	%	Homo sapiens
F	60.0	%	Homo sapiens
Fu	0.012	-	Homo sapiens
Fu	0.012	-	Homo sapiens
Fu	0.091	-	Mus musculus
Fu	0.048	-	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 14	Ki	=	52.0	nM	7.28	Inhibition of human recombinant full length CA14 by stopped-flow CO2 hydration m...	19119014
Carbonic anhydrase 1	Ki	=	62.0	nM	7.21	Inhibition of human recombinant full length CA1 by stopped-flow CO2 hydration me...	19119014
Carbonic anhydrase 2	Ki	=	65.0	nM	7.19	Inhibition of human recombinant full length CA2 by stopped-flow CO2 hydration me...	19119014
Carbonic anhydrase 1	IC50	=	80.0	nM	7.1	Known Inhibitors of Carbonic Anhydrase: Compounds which are CAIs are well known ...	-
Carbonic anhydrase 6	Ki	=	245.0	nM	6.61	Inhibition of human recombinant full length CA6 by stopped-flow CO2 hydration me...	19119014
Carbonic anhydrase 12	Ki	=	261.0	nM	6.58	Inhibition of human recombinant CA12 catalytic domain by stopped-flow CO2 hydrat...	19119014
Carbonic anhydrase 5B, mitochondrial	Ki	=	322.0	nM	6.49	Inhibition of human recombinant full length CA5B by stopped-flow CO2 hydration m...	19119014
Carbonic anhydrase 9	Ki	=	420.0	nM	6.38	Inhibition of human recombinant CA9 catalytic domain by stopped-flow CO2 hydrati...	19119014
Carbonic anhydrase 5A, mitochondrial	Ki	=	499.0	nM	6.3	Inhibition of human recombinant full length CA5A by stopped-flow CO2 hydration m...	19119014
Carbonic anhydrase 7	Ki	=	513.0	nM	6.29	Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration me...	19119014
Carbonic anhydrase 13	Ki	=	550.0	nM	6.26	Inhibition of mouse recombinant full length CA13 by stopped-flow CO2 hydration m...	19119014
Carbonic anhydrase 4	Ki	=	564.0	nM	6.25	Inhibition of human recombinant full length CA4 by stopped-flow CO2 hydration me...	19119014
Carbonic anhydrase 2	Kd	=	630.0	nM	6.2	Binding affinity to human recombinant CA II assessed as dissociation constant	39161321
CDGSH iron-sulfur domain-containing protein 1	Ki	=	2285.0	nM	5.64	Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M...	27687671
Broad substrate specificity ATP-binding cassette transporter ABCG2	IC50	=	3200.0	nM	5.5	Inhibition of ABCG2 (unknown origin) expressed in human HEK293-A cells membrane ...	35483322
Carbonic anhydrase 2	Kd	=	3140.0	nM	5.5	Displacement of dansylamide from human recombinant CA II expressed in Escherichi...	39161321
G-protein coupled receptor 35	Ki	=	3270.0	nM	5.49	Displacement of [3H]PSB-13253 from human recombinant GPR35 exprssed in CHO cells...	23888932
11-beta-hydroxysteroid dehydrogenase 1	IC50	=	3760.0	nM	5.42	Inhibition of mouse 11beta-HSD1 expressed in HEK293 cells assessed as conversion...	18653260
11-beta-hydroxysteroid dehydrogenase 1	IC50	=	3760.0	nM	5.42	Inhibition of human 11beta-HSD1 expressed in HEK293 cells assessed as conversion...	18653260
G-protein coupled receptor 35	EC50	=	6200.0	nM	5.21	Agonist activity at human GPR35 by Ca+2 release assay	23888932

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1415
-	10.6019/CHEMBL3885881	Rattus norvegicus	295
-	10.1101/2024.03.28.586928	ADMET	100
1433206	10.1021/jm00100a001	Rattus norvegicus	46
7966129	10.1021/jm00048a005	Rattus norvegicus	25
2724291	10.1021/jm00126a003	Rattus norvegicus	22
21051535	10.1124/dmd.110.034629	ADMET	21
1501234	10.1021/jm00094a022	Rattus norvegicus	19
16472241	10.2174/1570163043334794	Hepatotoxicity	18
3712385	10.1021/jm00156a011	Rattus norvegicus	18
-	10.1007/s00044-012-0086-y	Rattus norvegicus	16
7452697	10.1021/jm00186a024	Rattus norvegicus	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
19361209	10.1021/jm900025h	Rattus norvegicus	12
6737427	10.1021/jm00373a005	Rattus norvegicus	12
3735318	10.1021/jm00158a030	ADMET	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
7205867	10.1021/jm00133a024	Rattus norvegicus	10
7966129	10.1021/jm00048a005	Canis familiaris	10
6876086	10.1021/jm00362a017	Canis familiaris	10

Data from ChEMBL 36 via Core Engine