Compound Detail

CHEMBL686

MEFENAMIC ACID

💊 Approved Drug

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💊 Approved Drug

Cc1cccc(Nc2ccccc2C(=O)O)c1C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL686
Name	MEFENAMIC ACID
Phase	Approved
Structure Type	MOL
InChI Key	HYYBABOKPJLUIN-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Acide mefenamique Acido mefenamico CI-473 CN-35355 Contraflam Dysman-250 Dysman-500 Gardan INF-3355 J2.344B M01AG01 Mefenamate +13 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

241.3

MW (Da)

3.75

ALogP

HBA

HBD

49.3

PSA (Å²)

0.86

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1967
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Stem	-fenamic acid
USAN Year	1962

Extended Properties

Molecular Formula	C15H15NO2
MW	241.29
Aromatic Rings	2
Heavy Atoms	18
NP-Likeness	-0.81

Mechanism of Action

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

Indications

Dysmenorrhea Rheumatic Diseases Hemorrhage Pain Diabetes Mellitus

ATC Classification

M01AG01

mefenamic acid

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Black Box Warning

neurotoxicity

Country: United States

Black Box Warning

gastrointestinal toxicity

Country: United States

Black Box Warning

cardiotoxicity

Country: United States

Activity Summary

IC50 22 meas. best 6.94

EC50 6 meas. best 4.96

Ki 5 meas. best 10.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Nicotinate phosphoribosyltransferase CHEMBL4523354	Ki	10.3	10.3	0.1	1
Prostaglandin G/H synthase 1 CHEMBL221	IC50	6.94	5.77	116.0	2
Aldo-keto reductase family 1 member C2 CHEMBL5847	Ki	6.66	6.66	220.0	1
Aldo-keto reductase family 1 member C3 CHEMBL4681	Ki	6.52	6.52	300.0	1
Aldo-keto reductase family 1 member C3 CHEMBL4681	IC50	6.25	6.25	560.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	6.22	5.88	602.0	2
Aldo-keto reductase family 1 member C1 CHEMBL5905	Ki	6.09	6.09	810.0	1
Myeloperoxidase CHEMBL2439	IC50	6.01	5.835	980.0	2
Staphylococcus aureus CHEMBL352	IC50	5.87	5.87	1336.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	5.8	5.8	1600.0	1
Aldo-keto reductase family 1 member C1 CHEMBL5905	IC50	5.41	5.41	3910.0	1
Acetylcholinesterase CHEMBL4780	IC50	5.21	5.21	6120.0	1
Aldo-keto reductase family 1 member C2 CHEMBL5847	IC50	5.16	5.16	6970.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.96	4.96	10900.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL6007	EC50	4.8	4.5967	16000.0	3
Unchecked CHEMBL612545	IC50	4.61	4.3733	24800.0	3
NACHT, LRR and PYD domains-containing protein 3 CHEMBL3779755	IC50	4.6	4.6	25000.0	1
Bile salt export pump CHEMBL6020	IC50	4.24	4.24	57000.0	1
Dihydrofolate reductase CHEMBL202	Ki	4.14	4.14	72000.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	4.11	4.11	77000.0	1
NCI-H2171 CHEMBL2366213	EC50	4.03	4.03	93500.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	9.0	mL.min-1.g-1	Homo sapiens
Cmax	83000.0	nM	-
Cmax	26939.0	nM	Homo sapiens
T1/2	16.5	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Nicotinate phosphoribosyltransferase	Ki	=	0.05	nM	10.3	Inhibition of NAPRT (unknown origin)	-
Prostaglandin G/H synthase 1	IC50	=	116.0	nM	6.94	DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid)	-
Aldo-keto reductase family 1 member C2	Ki	=	220.0	nM	6.66	Inhibition of human recombinant AKR1C2 assessed as 1-acenaphthenol oxidation by ...	22881866
Aldo-keto reductase family 1 member C3	Ki	=	300.0	nM	6.52	Inhibition of human recombinant AKR1C3 assessed as 1-acenaphthenol oxidation by ...	22881866
Aldo-keto reductase family 1 member C3	IC50	=	560.0	nM	6.25	Inhibition of AKR1C3 (unknown origin)	23454516
Prostaglandin G/H synthase 2	IC50	=	602.0	nM	6.22	DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid)	-
Aldo-keto reductase family 1 member C1	Ki	=	810.0	nM	6.09	Inhibition of human recombinant AKR1C1 assessed as 1-acenaphthenol oxidation by ...	22881866
Myeloperoxidase	IC50	=	980.0	nM	6.01	Inhibition of recombinant MPO (unknown origin) assessed as reduction in taurine ...	28671460
Staphylococcus aureus	IC50	=	1336.0	nM	5.87	PUBCHEM_BIOASSAY: Inhibitors of Bacterial Quorum Sensing Structure Activity Rela...	-
Aldo-keto reductase family 1 member B10	IC50	=	1600.0	nM	5.8	Inhibition of wild-type N-terminal 6-His tagged AKR1B10 (unknown origin) express...	25375908
Myeloperoxidase	IC50	=	2210.0	nM	5.66	Inhibition of recombinant MPO (unknown origin) assessed as reduction in LDL oxid...	28671460
Prostaglandin G/H synthase 2	IC50	=	2900.0	nM	5.54	Inhibition of COX2 (unknown origin)	23454516
Aldo-keto reductase family 1 member C1	IC50	=	3910.0	nM	5.41	Inhibition of AKR1C1 (unknown origin)	23454516
Acetylcholinesterase	IC50	=	6120.0	nM	5.21	Inhibition of Torpedo californica eel AChE using acetylthiocholine/DTNB as subst...	-
Aldo-keto reductase family 1 member C2	IC50	=	6970.0	nM	5.16	Inhibition of AKR1C2 (unknown origin)	23454516
NON-PROTEIN TARGET	EC50	=	10900.0	nM	4.96	Antiviral activity against JC polyomavirus M1/SVEdelta infected in human SVG-A c...	19258267
Transient receptor potential cation channel subfamily A member 1	EC50	=	16000.0	nM	4.8	Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase i...	30878828
Transient receptor potential cation channel subfamily A member 1	EC50	=	16595.87	nM	4.78	Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase i...	30878828
Unchecked	IC50	=	24800.0	nM	4.61	Inhibition of soybean 15-LOX	37862815
Prostaglandin G/H synthase 1	IC50	=	25000.0	nM	4.6	Inhibition of COX1 (unknown origin)	23454516

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1404
-	10.6019/CHEMBL3885881	Rattus norvegicus	276
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
-	10.1007/s00044-012-0016-z	Rattus norvegicus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
22577085	10.1124/dmd.112.046102	ADMET	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
-	10.1007/s00044-013-0516-5	Rattus norvegicus	7
-	10.1007/s00044-012-0016-z	No relevant target	7
38991154	10.1021/acs.jmedchem.4c00721	Mus musculus	6
19398345	10.1016/j.bmc.2009.03.065	Rattus norvegicus	6
28671460	10.1021/acs.jmedchem.7b00285	Myeloperoxidase	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
30878828	10.1016/j.ejmech.2019.02.074	Transient receptor potential cation channel subfamily A member 1	4
14521410	10.1021/jm030191r	Beta-lactamase	4
16455248	10.1016/j.bmcl.2006.01.033	Mus musculus	3
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	3
14521410	10.1021/jm030191r	Chymotrypsinogen A	3
21273081	10.1016/j.bmc.2010.12.050	Transthyretin	3

Data from ChEMBL 36 via Core Engine