Compound Detail

CHEMBL191

LOSARTAN

💊 Approved Drug

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💊 Approved Drug

CCCCc1nc(Cl)c(CO)n1Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL191
Name	LOSARTAN
Phase	Approved
Structure Type	MOL
InChI Key	PSIFNNKUMBGKDQ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Allisartan Angizaar Dup-89 E-3174 Exp-3174 EXP3174 HGP-1405 HGP1405 Losartan Losartan carboxylic acid Losartic Lozap +1 more

Targets

185

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

422.9

MW (Da)

4.27

ALogP

HBA

HBD

92.5

PSA (Å²)

0.44

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1995
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Stem	-sartan
USAN Year	1992

Extended Properties

Molecular Formula	C22H23ClN6O
MW	422.92
Aromatic Rings	4
Heavy Atoms	30
NP-Likeness	-1.16

Indications

Cardiovascular Diseases Diabetic Nephropathies Essential Hypertension Glioblastoma Glomerulonephritis, IGA Heart Failure Hyperoxaluria, Primary Hypertension Hypertension, Pulmonary Hypertrophy, Left Ventricular Kidney Diseases Marfan Syndrome Non-alcoholic Fatty Liver Disease Non-alcoholic Fatty Liver Disease Proteinuria Renal Insufficiency, Chronic Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Anemia, Sickle Cell Aortic Valve Insufficiency

ATC Classification

C09CA01

losartan

Level 1: CARDIOVASCULAR SYSTEM

Level 2: AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM

Activity Summary

IC50 128 meas. best 9.48

Kd 32 meas. best 8.8

Ki 24 meas. best 8.85

EC50 1 meas. best 6.46

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Type-1 angiotensin II receptor CHEMBL227	IC50	9.48	7.8744	0.3	16
HASMC CHEMBL614150	IC50	9.15	9.15	0.7	1
Unchecked CHEMBL612545	IC50	9.09	7.8623	0.8	13
Unchecked CHEMBL612545	Ki	8.85	8.2017	1.4	6
Type-1 angiotensin II receptor CHEMBL3948	Kd	8.8	7.9444	1.6	9
Oryctolagus cuniculus CHEMBL374	Kd	8.8	8.425	1.6	6
Angiotensin II receptor CHEMBL2094256	Kd	8.8	8.522	1.6	5
Angiotensin II receptor (AT-1) type-1 CHEMBL2094250	IC50	8.74	7.7936	1.8	14
Angiotensin II receptor (AT-1) type-1 CHEMBL2094250	Ki	8.72	8.3067	1.9	3
Type-1 angiotensin II receptor CHEMBL3948	IC50	8.52	7.4914	3.0	14
Type-1 angiotensin II receptor CHEMBL227	Kd	8.48	8.48	3.3	1
Type-1 angiotensin II receptor B CHEMBL263	Ki	8.44	7.7633	3.6	3
Unchecked CHEMBL612545	Kd	8.43	8.0083	3.7	6
Angiotensin II receptor CHEMBL2094112	IC50	8.34	7.5678	4.6	9
Type-1 angiotensin II receptor B CHEMBL263	IC50	8.3	7.477	5.0	10
Type-1 angiotensin II receptor CHEMBL227	Ki	8.3	7.9925	5.0	4
Type-2 angiotensin II receptor CHEMBL4607	Ki	8.26	8.26	5.5	2
Oryctolagus cuniculus CHEMBL374	IC50	8.21	7.81	6.1	5
Type-1 angiotensin II receptor A CHEMBL329	IC50	8.17	7.945	6.7	2
Angiotensin II receptor CHEMBL2094256	IC50	8.1	7.55	8.0	4
Type-1 angiotensin II receptor A CHEMBL329	Kd	8.0	7.7	10.0	2
Type-2 angiotensin II receptor CHEMBL4607	IC50	7.96	7.88	11.0	3
Type-1 angiotensin II receptor A CHEMBL329	Ki	7.86	7.85	13.9	2
Type-1 angiotensin II receptor CHEMBL1671613	IC50	7.75	7.75	18.0	2
Angiotensin-converting enzyme CHEMBL1808	IC50	7.72	7.72	19.0	1
Rattus norvegicus CHEMBL376	IC50	7.72	7.72	19.0	1
Angiotensin II receptor CHEMBL2094112	Ki	7.5	7.5	31.6	1
Type-1 angiotensin II receptor CHEMBL3374	IC50	7.02	6.6854	95.0	13
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	6.8	6.8	160.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	6.54	6.54	288.4	1
Type-1 angiotensin II receptor CHEMBL3374	EC50	6.46	6.46	350.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	6.05	6.05	890.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.94	5.94	1148.2	1
Cytochrome P450 2C9 CHEMBL3397	IC50	5.54	5.54	2882.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	5.46	5.46	3467.4	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.46	5.46	3493.0	1
Platelet glycoprotein VI CHEMBL3308912	IC50	5.4	5.185	4000.0	4
Type-2 angiotensin II receptor CHEMBL257	IC50	5.13	4.52	7400.0	3
Bile salt export pump CHEMBL6020	IC50	5.07	5.07	8500.0	2
Phosphodiesterase 3 CHEMBL2094125	IC50	4.89	4.89	13000.0	1
Thromboxane A2 receptor CHEMBL2069	IC50	4.7	4.7	20000.0	1
Phosphodiesterase 4 CHEMBL2093863	IC50	4.58	4.58	26000.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	4.46	4.46	35000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	-17707.0	-	-
AUC	-3362.0	-	-
AUC	12400.0	ng.hr.mL-1	Rattus norvegicus
AUC	74800.0	ng.hr.mL-1	Rattus norvegicus
AUC	12400.0	ng.hr.mL-1	Rattus norvegicus
AUC	74800.0	ng.hr.mL-1	Rattus norvegicus
AUC	494.2	ng.hr.mL-1	Homo sapiens
AUC	473.0	ng.hr.mL-1	Homo sapiens
AUC	366.1	ng.hr.mL-1	Homo sapiens
AUC	636.7	ng.hr.mL-1	Homo sapiens
AUC	455.2	ng.hr.mL-1	Homo sapiens
AUC	518.8	ng.hr.mL-1	Homo sapiens
AUC	503.6	ng.hr.mL-1	Homo sapiens
AUC	413.2	ng.hr.mL-1	Homo sapiens
CL	8.2	mL.min-1.kg-1	Homo sapiens
CL	7.3	mL.min-1.kg-1	Homo sapiens
CL	8.2	mL.min-1.kg-1	Homo sapiens
CL	8.2	mL.min-1.kg-1	Homo sapiens
CL	31.67	mL.min-1.kg-1	Homo sapiens
CL	26.67	mL.min-1.kg-1	Homo sapiens
CL	30.0	mL.min-1.kg-1	Homo sapiens
CL	31.67	mL.min-1.kg-1	Homo sapiens
CL	21.67	mL.min-1.kg-1	Homo sapiens
CL	27.67	mL.min-1.kg-1	Homo sapiens
CL	30.33	mL.min-1.kg-1	Homo sapiens
CL	28.33	mL.min-1.kg-1	Homo sapiens
Cmax	65024.12	nM	Rattus norvegicus
Cmax	65024.12	nM	Rattus norvegicus
Cmax	816.23	nM	Homo sapiens
Cmax	609.1	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Type-1 angiotensin II receptor	IC50	=	0.33	nM	9.48	Inhibition of angiotensin AT1 receptor	22727371
HASMC	IC50	=	0.71	nM	9.15	Inhibitory activity against Ang II-induced proliferation of human aortic smooth ...	8576904
Unchecked	IC50	=	0.82	nM	9.09	Antagonist activity at angiotensin AT1 receptor in rat adrenal cortical membrane...	21071232
Unchecked	Ki	=	1.41	nM	8.85	Displacement of [125I]Angiotensin-2 from angiotensin AT1 receptor in Sprague-Daw...	23122933
Oryctolagus cuniculus	Kd	=	1.585	nM	8.8	Tested for inhibitory activity against angiotensin II induced contraction in rab...	-
Angiotensin II receptor	Kd	=	1.585	nM	8.8	Inhibition of angiotensin II induced contraction in thoracic aortic rings from N...	-
Angiotensin II receptor	Kd	=	1.585	nM	8.8	Inhibition of angiotensin II induced contractions in rabbit aortic ring preparat...	-
Type-1 angiotensin II receptor	Kd	=	1.585	nM	8.8	In vitro binding affinity against Angiotensin II receptor in rabbit aorta rings	-
Unchecked	IC50	=	1.64	nM	8.79	Displacement of [125I]Angiotensin-2 from angiotensin AT1 receptor in Sprague-Daw...	23122933
Angiotensin II receptor (AT-1) type-1	IC50	=	1.8	nM	8.74	Inhibitory concentration against [125 I]Ang II binding to rat pituitary membrane...	9083479
Angiotensin II receptor (AT-1) type-1	Ki	=	1.9	nM	8.72	Displacement of [125I]-Ang II from rat liver membrane angiotensin II type 1 (AT1...	15537355
Unchecked	Ki	=	2.53	nM	8.6	Displacement of [125I]-angiotensin 2 from angiotensin AT1 receptor in VSMC of Sp...	24613628
Oryctolagus cuniculus	Kd	=	2.512	nM	8.6	Potency of the Angiotensin II-induced contraction of rabbit aortic strips	-
Oryctolagus cuniculus	Kd	=	2.951	nM	8.53	Antagonism against A-2 induced contraction of aortic rings from rabbit.	8667363
Type-1 angiotensin II receptor	IC50	=	3.0	nM	8.52	Inhibitory activity against Angiotensin II receptor, type 1 induced contractions...	-
Type-1 angiotensin II receptor	IC50	=	3.236	nM	8.49	Displacement of [125I-Sar1-Ile8]Ang2 from human AT1 receptor expressed in HEK293...	27480029
Type-1 angiotensin II receptor	Kd	=	3.311	nM	8.48	Antagonist activity at angiotensin AT1 receptor	21071232
Angiotensin II receptor	Kd	=	3.311	nM	8.48	Inhibition of angiotensin II-induced contractions in rabbit aorta in vitro.	8576904
Unchecked	IC50	=	3.54	nM	8.45	Displacement of [125I]-angiotensin 2 from angiotensin AT1 receptor in VSMC of Sp...	24613628
Type-1 angiotensin II receptor B	Ki	=	3.6	nM	8.44	Displacement of [125I]-Sar1-Ile8-A II from rat adrenal Angiotensin-1 (AT-1) rece...	8057285

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	298
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	60
23118328	10.1124/dmd.112.046292	Homo sapiens	40
24200932	10.1016/j.bmc.2013.10.017	Rattus norvegicus	20
19863054	10.1021/jm9003957	Rattus norvegicus	19
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
22750010	10.1016/j.bmc.2012.06.011	Rattus norvegicus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
-	10.6019/CHEMBL4689842	HEK-293T	10
-	10.6019/CHEMBL4689842	U2OS	10
8064808	10.1021/jm00043a020	Rattus norvegicus	9
8568823	10.1021/jm950450f	Rattus norvegicus	9
-	10.6019/CHEMBL4689842	Fibroblast	9
8246227	10.1021/jm00075a014	Rattus norvegicus	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
20070106	10.1021/jm901371v	Homo sapiens	8
17064065	10.1021/jm0603163	Rattus norvegicus	7
18318468	10.1021/jm7011563	Rattus norvegicus	7

Data from ChEMBL 36 via Core Engine