Compound Detail

CHEMBL154

NAPROXEN

💊 Approved Drug

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💊 Approved Drug

COc1ccc2cc([C@H](C)C(=O)O)ccc2c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL154
Name	NAPROXEN
Phase	Approved
Structure Type	MOL
InChI Key	CMWTZPSULFXXJA-VIFPVBQESA-N
Therapeutic	✓ Yes

Known Names

Arthrosin 250 Arthrosin 250 ec Arthrosin 500 Arthrosin 500 ec Condrotec Ec-naprosyn Feminax ultra Grenoxal Kenosyn Laraflex Napratec op Naprosyn +18 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

230.3

MW (Da)

3.04

ALogP

HBA

HBD

46.5

PSA (Å²)

0.88

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1976
Availability	OTC
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Year

1970

Extended Properties

Molecular Formula	C14H14O3
MW	230.26
Aromatic Rings	2
Heavy Atoms	17
NP-Likeness	0.05

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Cyclooxygenase inhibitor	INHIBITOR	Cyclooxygenase	✓	✓

Indications

Acute Pain Arthralgia Arthritis Arthritis, Gouty Arthritis, Juvenile Arthritis, Rheumatoid Back Pain Bursitis Common Cold Dysmenorrhea Fever Gout Headache Muscle Cramp Myalgia Osteoarthritis Pain Rheumatic Diseases Spondylitis Spondylitis, Ankylosing

ATC Classification

G02CC02

naproxen

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: OTHER GYNECOLOGICALS

M01AE02

naproxen

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

M02AA12

naproxen

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN

Drug Warnings

Black Box Warning

cardiotoxicity

Country: United States

Black Box Warning

gastrointestinal toxicity

Country: United States

Black Box Warning

neurotoxicity

Country: United States

Activity Summary

IC50 61 meas. best 7.22

Ki 7 meas. best 8.24

EC50 1 meas.

Kd 1 meas. best 4.58

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	Ki	8.24	7.6933	5.7	3
Cyclooxygenase CHEMBL2095157	IC50	7.22	7.22	60.0	1
Prostaglandin G/H synthase 1 CHEMBL2949	IC50	7.21	5.4678	61.0	9
Aldo-keto reductase family 1 member C3 CHEMBL4681	IC50	6.75	6.445	180.0	4
MC9 CHEMBL614867	IC50	6.7	6.59	200.0	2
Prostaglandin G/H synthase 1 CHEMBL221	IC50	6.68	5.5114	211.0	7
Prostaglandin G/H synthase 2 CHEMBL230	IC50	6.05	4.9817	900.0	12
Hormone-sensitive lipase CHEMBL5582	IC50	5.92	5.92	1200.0	1
Aldo-keto reductase family 1 member C2 CHEMBL5847	IC50	5.9	5.4333	1260.0	3
Solute carrier family 22 member 6 CHEMBL1777665	Ki	5.7	5.7	2000.0	1
Prostaglandin G/H synthase 2 CHEMBL4102	IC50	5.47	5.47	3360.0	1
Replicase polyprotein 1ab CHEMBL4523582	IC50	5.46	5.46	3450.0	1
Unchecked CHEMBL612545	IC50	5.45	4.8375	3520.0	4
Solute carrier family 22 member 6 CHEMBL1641347	IC50	5.24	5.24	5800.0	1
Prostaglandin G/H synthase 1 CHEMBL2860	IC50	4.96	4.96	11000.0	1
Prostaglandin-H2 D-isomerase CHEMBL4334	IC50	4.89	4.89	13000.0	1
Influenza A virus CHEMBL613740	IC50	4.8	4.4	16000.0	2
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL312	IC50	4.77	4.77	17000.0	1
Unchecked CHEMBL612545	Kd	4.58	4.58	26000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	63539.17	ng.hr.mL-1	Mus musculus
AUC	207800.0	ng.hr.mL-1	Rattus norvegicus
CL	0.04	mL.min-1.kg-1	Canis lupus familiaris
CL	0.07	mL.min-1.kg-1	Homo sapiens
CL	0.41	mL.min-1.kg-1	Rattus norvegicus
CL	0.61	mL.min-1.kg-1	Macaca
CL	3.0	mL.min-1.g-1	Homo sapiens
CL	5.86	mL.min-1.kg-1	Homo sapiens
CL	4.91	uL.min-1.(10^6cells)-1	Homo sapiens
CL	16.4	uL.min-1.(10^6cells)-1	Homo sapiens
CL	0.106	mL.min-1.kg-1	Homo sapiens
CL	2.2	mL.min-1.kg-1	Mus musculus
CL	12.7	uL.min-1.(10^6cells)-1	Homo sapiens
CL	0.1	mL.min-1.kg-1	Homo sapiens
CL	21.0	mL.min-1.kg-1	Homo sapiens
CL	0.55	mL.min-1.kg-1	Rattus norvegicus
CL	0.27	mL.min-1.kg-1	Macaca fascicularis
CL	0.073	mL.min-1.kg-1	Homo sapiens
Cmax	17.07	ug/g	Mus musculus
Cmax	238730.13	nM	Rattus norvegicus
F	80.0	%	Homo sapiens
F	100.0	%	Homo sapiens
Fu	0.018	-	Not specified
Fu	0.989	-	Homo sapiens
Fu	0.01	-	Homo sapiens
Fu	5.36e-05	-	Rattus norvegicus
Fu	3.26e-05	-	Macaca fascicularis
Fu	1.21e-05	-	Homo sapiens
Ka	7.73	10'6/M	Equus caballus
MRT	0.6112	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	Ki	=	5.7	nM	8.24	Binding affinity to beta-amyloid plaques	20036557
Unchecked	Ki	=	5.7	nM	8.24	Binding affinity to amyloid beta fibrils	21802289
Cyclooxygenase	IC50	=	60.0	nM	7.22	In vitro inhibitory activity against Prostaglandin G/H synthase in rat neutrophi...	3086558
Prostaglandin G/H synthase 1	IC50	=	61.0	nM	7.21	Inhibition of COX1 in ram seminal vesicles using arachidonic acid as substrate a...	27486833
Prostaglandin G/H synthase 1	IC50	=	180.0	nM	6.75	Inhibition of ovine COX1	23200247
Aldo-keto reductase family 1 member C3	IC50	=	180.0	nM	6.75	S-Tetralol Oxidation Assay: the inhibitory potency of the individual compounds a...	-
Aldo-keto reductase family 1 member C3	IC50	=	180.0	nM	6.75	Inhibition of human recombinant AKR1C3 using S-tetralol as substrate assessed as...	27486833
Prostaglandin G/H synthase 1	IC50	=	180.0	nM	6.75	Inhibition of ovine COX-1	21280601
MC9	IC50	=	200.0	nM	6.7	Inhibition of PGF2alpha production in mouse MC9 cells	18498150
Prostaglandin G/H synthase 1	IC50	=	211.0	nM	6.68	DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid)	-
Unchecked	Ki	=	250.0	nM	6.6	Binding affinity to Influenza A virus nucleoprotein by surface plasmon resonance...	30028133
MC9	IC50	=	330.0	nM	6.48	Inhibition of PGF2apha production in arachidonic acid-stimulated mouse MC9 cells	18498150
Prostaglandin G/H synthase 1	IC50	=	350.0	nM	6.46	Compound was tested in vitro for inhibition of human platelet Prostaglandin G/H ...	-
Aldo-keto reductase family 1 member C3	IC50	=	480.0	nM	6.32	Inhibition of recombinant human AKR1C3	16183274
Prostaglandin G/H synthase 2	IC50	=	900.0	nM	6.05	Inhibition of COX2 (unknown origin) using arachidonic acid as substrate assessed...	27486833
Aldo-keto reductase family 1 member C3	IC50	=	1100.0	nM	5.96	Inhibition of human recombinant N-terminal His6-tagged AKR1C3 expressed in Esche...	22877157
Hormone-sensitive lipase	IC50	=	1200.0	nM	5.92	Inhibition of HSL in Wistar rat isolated fat cells by spectrophotometric assay	18808096
Aldo-keto reductase family 1 member C2	IC50	=	1260.0	nM	5.9	Inhibition of human recombinant AKR1C2 using S-tetralol as substrate assessed as...	27486833
Aldo-keto reductase family 1 member C2	IC50	=	1260.0	nM	5.9	S-Tetralol Oxidation Assay: the inhibitory potency of the individual compounds a...	-
Solute carrier family 22 member 6	Ki	=	2000.0	nM	5.7	TP_TRANSPORTER: inhibition of PAH uptake in Xenopus laevis oocytes	10220563

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1406
-	10.6019/CHEMBL3885881	Rattus norvegicus	1141
-	10.5281/zenodo.13943903	ADMET	89
-	10.1039/C5MD00551E	No relevant target	28
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
1560438	10.1021/jm00085a012	Rattus norvegicus	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
32985885	10.1021/acs.jmedchem.0c01033	ADMET	11
30028133	10.1021/acs.jmedchem.8b00557	Unchecked	9
16789751	10.1021/jm060230+	ADMET	9
20926620	10.1124/dmd.110.035600	HEK293	9
17383881	10.1016/j.bmc.2007.03.026	RAW264.7	9
15920768	10.1002/jps.20373	ADMET	8
25868745	10.1016/j.bmc.2015.03.049	Mus musculus	8
10649977	10.1021/jm991106b	Rattus norvegicus	8
36074863	10.1021/acs.jmedchem.2c00878	Candida albicans	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
25466180	10.1016/j.bmcl.2014.10.096	Rattus norvegicus	7
16872141	10.1021/np0601556	Mus musculus	7

Data from ChEMBL 36 via Core Engine