Scroll

mefenamic acid 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
anti-inflammatory, anthranilic acid derivatives	1663	61-68-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: mefenamic acid mefenacid mephenamic acid mefenamate	A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase. Molecular weight: 241.29 Formula: C15H15NO2 CLOGP: 5.14 LIPINSKI: 1 HAC: 3 HDO: 2 TPSA: 49.33 ALOGS: -4.25 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

mefenamic acid
mefenacid
mephenamic acid
mefenamate

A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.

Molecular weight: 241.29
Formula: C15H15NO2
CLOGP: 5.14
LIPINSKI: 1
HAC: 3
HDO: 2
TPSA: 49.33
ALOGS: -4.25
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1	g	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.02 mg/mL	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	1 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	74.01 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
March 28, 1967	FDA	SHIONOGI INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Infusion site coldness	117.76	17.39	21	8336	195	63480470
Gamma-glutamyltransferase decreased	109.52	17.39	21	8336	299	63480366
Infusion site induration	81.50	17.39	21	8336	1201	63479464
Spinal pain	75.09	17.39	36	8321	13103	63467562
Post-traumatic neck syndrome	70.50	17.39	21	8336	2053	63478612
Mean cell haemoglobin decreased	69.39	17.39	26	8331	5153	63475512
Vasodilatation	67.52	17.39	21	8336	2374	63478291
Feeling cold	54.97	17.39	36	8321	23852	63456813
Vascular malformation	53.82	17.39	12	8345	368	63480297
Paranasal cyst	53.00	17.39	12	8345	395	63480270
Stress	52.68	17.39	54	8303	67113	63413552
Inflammatory marker increased	52.46	17.39	23	8334	6816	63473849
Infusion site haemorrhage	52.06	17.39	21	8336	5065	63475600
Vein disorder	51.84	17.39	21	8336	5120	63475545
Retinal detachment	48.81	17.39	21	8336	5948	63474717
Peripheral coldness	45.34	17.39	25	8332	12140	63468525
Incontinence	43.61	17.39	24	8333	11608	63469057
Urinoma	42.23	17.39	7	8350	40	63480625
Mastoiditis	41.66	17.39	12	8345	1043	63479622
Blood creatinine decreased	37.26	17.39	17	8340	5528	63475137
Injection site bruising	35.23	17.39	35	8322	41875	63438790
Tendon disorder	33.35	17.39	16	8341	5827	63474838
Bladder prolapse	33.23	17.39	12	8345	2144	63478521
Angioedema	33.04	17.39	36	8321	47929	63432736
Oropharyngeal pain	32.09	17.39	50	8307	94437	63386228
Oral lichenoid reaction	31.06	17.39	6	8351	89	63480576
Poor venous access	30.92	17.39	21	8336	14764	63465901
Rectal prolapse	30.42	17.39	11	8346	1972	63478693
Toothache	30.35	17.39	23	8334	19176	63461489
Skin sensitisation	30.21	17.39	9	8348	880	63479785
Body temperature decreased	29.19	17.39	23	8334	20296	63460369
Chills	29.18	17.39	53	8304	113325	63367340
Urine osmolarity increased	28.91	17.39	6	8351	130	63480535
Musculoskeletal disorder	28.87	17.39	23	8334	20621	63460044
Neutrophil count decreased	28.31	17.39	36	8321	56370	63424295
Immunodeficiency	27.12	17.39	22	8335	20232	63460433
Blood potassium increased	26.89	17.39	21	8336	18288	63462377
Otitis media	26.72	17.39	13	8344	4878	63475787
Death	25.07	17.39	9	8348	374372	63106293
Enthesopathy	24.88	17.39	15	8342	8599	63472066
Metastases to bone	24.35	17.39	21	8336	20998	63459667
Dactylitis	24.05	17.39	10	8347	2602	63478063
Urticaria	23.62	17.39	61	8296	165741	63314924
Arteriospasm coronary	23.05	17.39	11	8346	3957	63476708
Headache	22.96	17.39	152	8205	633089	62847576
Hepatic function abnormal	22.37	17.39	26	8331	37116	63443549
Pain in jaw	22.20	17.39	28	8329	43468	63437197
Eosinophil count increased	21.62	17.39	15	8342	10913	63469752
Photosensitivity reaction	21.59	17.39	17	8340	14977	63465688
Thermal burn	21.36	17.39	12	8345	6034	63474631
Nephrogenic diabetes insipidus	21.24	17.39	7	8350	952	63479713
Gastritis	20.62	17.39	25	8332	37278	63443387
Haemangioma	20.41	17.39	9	8348	2703	63477962
Injection site inflammation	20.35	17.39	10	8347	3833	63476832
Renal ischaemia	19.75	17.39	6	8351	627	63480038
Renal papillary necrosis	19.66	17.39	5	8352	271	63480394
Gastrointestinal inflammation	19.45	17.39	11	8346	5601	63475064
Mononeuropathy multiplex	19.38	17.39	5	8352	287	63480378
Drug reaction with eosinophilia and systemic symptoms	19.23	17.39	23	8334	33813	63446852
Flushing	19.18	17.39	35	8322	75052	63405613
Cerebellar haemangioma	19.00	17.39	4	8353	93	63480572
Impaired driving ability	18.84	17.39	10	8347	4501	63476164
Peripheral swelling	18.81	17.39	77	8280	265865	63214800
Rabbit syndrome	18.74	17.39	5	8352	327	63480338
Injection site mass	18.36	17.39	17	8340	18639	63462026
Alopecia	18.14	17.39	11	8346	337525	63143140
Abdominal pain upper	18.08	17.39	64	8293	206380	63274285
Menopausal symptoms	17.98	17.39	8	8349	2453	63478212
Vitamin D decreased	17.82	17.39	13	8344	10229	63470436
Road traffic accident	17.78	17.39	23	8334	36609	63444056
Throat tightness	17.69	17.39	19	8338	24868	63455797
Crystal nephropathy	17.44	17.39	6	8351	930	63479735
Tubulointerstitial nephritis	17.42	17.39	17	8340	19886	63460779

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Heat stroke	66.75	23.67	14	1584	951	34954382
Ankylosing spondylitis	50.49	23.67	16	1582	5588	34949745
Brain stem syndrome	37.93	23.67	8	1590	557	34954776
Anhidrosis	36.58	23.67	6	1592	103	34955230
Exposure to communicable disease	34.39	23.67	6	1592	151	34955182
Vanishing bile duct syndrome	28.16	23.67	7	1591	1011	34954322
Mydriasis	27.91	23.67	11	1587	7226	34948107
Alopecia	27.83	23.67	16	1582	24339	34930994

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Infusion site coldness	119.02	16.89	21	8910	218	79735239
Gamma-glutamyltransferase decreased	109.08	16.89	21	8910	363	79735094
Infusion site induration	86.40	16.89	21	8910	1114	79734343
Post-traumatic neck syndrome	73.65	16.89	21	8910	2073	79733384
Spinal pain	69.16	16.89	34	8897	15358	79720099
Mean cell haemoglobin decreased	68.83	16.89	26	8905	6198	79729259
Vasodilatation	64.92	16.89	21	8910	3170	79732287
Infusion site haemorrhage	61.76	16.89	21	8910	3699	79731758
Feeling cold	56.65	16.89	37	8894	28692	79706765
Vascular malformation	55.20	16.89	12	8919	386	79735071
Vein disorder	54.97	16.89	21	8910	5161	79730296
Paranasal cyst	53.60	16.89	12	8919	443	79735014
Heat stroke	46.35	16.89	14	8917	1689	79733768
Retinal detachment	43.26	16.89	21	8910	9226	79726231
Incontinence	42.81	16.89	24	8907	14140	79721317
Peripheral coldness	42.76	16.89	25	8906	15945	79719512
Stress	41.80	16.89	48	8883	79564	79655893
Injection site bruising	40.73	16.89	35	8896	40967	79694490
Bladder prolapse	39.83	16.89	12	8919	1435	79734022
Death	39.05	16.89	8	8923	566506	79168951
Mastoiditis	37.89	16.89	12	8919	1692	79733765
Angioedema	35.21	16.89	43	8888	75992	79659465
Blood creatinine decreased	34.30	16.89	17	8914	7808	79727649
Toothache	32.86	16.89	23	8908	19947	79715510
Headache	32.60	16.89	152	8779	653620	79081837
Poor venous access	32.45	16.89	22	8909	18127	79717330
Urinoma	32.29	16.89	7	8924	222	79735235
Oropharyngeal pain	31.26	16.89	49	8882	109304	79626153
Rectal prolapse	31.15	16.89	11	8920	2167	79733290
Skin sensitisation	30.64	16.89	9	8922	986	79734471
Oral lichenoid reaction	30.28	16.89	6	8925	121	79735336
Urticaria	30.10	16.89	65	8866	185136	79550321
Inflammatory marker increased	29.24	16.89	17	8914	10723	79724734
Immunodeficiency	28.86	16.89	22	8909	21746	79713711
Body temperature decreased	27.07	16.89	25	8906	32120	79703337
Anhidrosis	26.68	16.89	6	8925	226	79735231
Otitis media	25.98	16.89	13	8918	6093	79729364
Chills	25.76	16.89	56	8875	160178	79575279
Urine osmolarity increased	25.17	16.89	6	8925	293	79735164
Musculoskeletal disorder	24.81	16.89	20	8911	21428	79714029
Metastases to bone	24.56	16.89	21	8910	24406	79711051
Pain in jaw	24.51	16.89	28	8903	46123	79689334
Tendon disorder	23.98	16.89	13	8918	7173	79728284
Injection site erythema	23.69	16.89	36	8895	78161	79657296
Blood potassium increased	23.18	16.89	22	8909	29253	79706204
Haemangioma	22.36	16.89	9	8922	2536	79732921
Injection site haemorrhage	22.17	16.89	21	8910	27849	79707608
Vanishing bile duct syndrome	21.75	16.89	8	8923	1770	79733687
Injection site inflammation	21.57	16.89	10	8921	3966	79731491
Neutrophil count decreased	21.36	16.89	38	8893	93921	79641536
Thermal burn	21.28	16.89	12	8919	7148	79728309
Abdominal pain upper	21.14	16.89	64	8867	223755	79511702
Menopausal symptoms	20.98	16.89	8	8923	1955	79733502
Peripheral swelling	20.86	16.89	72	8859	269545	79465912
Vitamin D decreased	20.33	16.89	13	8918	9712	79725745
Pain in extremity	19.77	16.89	87	8844	364451	79371006
Cerebellar haemangioma	19.65	16.89	4	8927	93	79735364
Injection site mass	19.57	16.89	17	8914	20167	79715290
Crystal nephropathy	19.49	16.89	7	8924	1448	79734009
Rabbit syndrome	19.10	16.89	5	8926	358	79735099
Road traffic accident	19.09	16.89	24	8907	43640	79691817
Therapeutic product effect incomplete	18.89	16.89	46	8885	141599	79593858
Gastritis	18.83	16.89	25	8906	47968	79687489
Post herpetic neuralgia	18.74	16.89	8	8923	2613	79732844
Impaired driving ability	18.64	16.89	10	8921	5405	79730052
Tubulointerstitial nephritis	18.31	16.89	22	8909	38213	79697244
Arthritis	18.28	16.89	40	8891	114840	79620617
Renal papillary necrosis	18.26	16.89	5	8926	425	79735032
Bone pain	17.36	16.89	26	8905	55716	79679741
Renal ischaemia	17.12	16.89	6	8925	1156	79734301

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	M01AG01	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Fenamates
FDA CS	M0001335	Anti-Inflammatory Agents, Non-Steroidal
FDA MoA	N0000000160	Cyclooxygenase Inhibitors
MeSH PA	D000700	Analgesics
MeSH PA	D018712	Analgesics, Non-Narcotic
MeSH PA	D000893	Anti-Inflammatory Agents
MeSH PA	D000894	Anti-Inflammatory Agents, Non-Steroidal
MeSH PA	D018501	Antirheumatic Agents
MeSH PA	D016861	Cyclooxygenase Inhibitors
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D018689	Sensory System Agents
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory agent
CHEBI has role	CHEBI:35493	anti-pyretic
CHEBI has role	CHEBI:35544	cyclooxygenase inhibitors
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:35842	anti-rheumatic drugs
CHEBI has role	CHEBI:78298	environmental contaminants
FDA EPC	N0000175722	Nonsteroidal Anti-inflammatory Drug

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Pain	indication	22253000
Dysmenorrhea	indication	266599000
Vascular headache	off-label use	128187005
Peptic ulcer	contraindication	13200003	DOID:750
Myocardial infarction	contraindication	22298006	DOID:5844
Hypertensive disorder	contraindication	38341003	DOID:10763
Gastrointestinal ulcer	contraindication	40845000
Chronic heart failure	contraindication	48447003
Disorder of cardiovascular system	contraindication	49601007	DOID:1287
Blood coagulation disorder	contraindication	64779008	DOID:1247
Gastrointestinal hemorrhage	contraindication	74474003
Kidney disease	contraindication	90708001	DOID:557
Coronary artery bypass graft	contraindication	232717009
Disease of liver	contraindication	235856003	DOID:409
Pregnancy, function	contraindication	289908002
Cardiovascular event risk	contraindication	395112001
Smokes tobacco daily	contraindication	449868002

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.43	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN	INHIBITOR	IC50	4.78	WOMBAT-PK	CHEMBL
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	6.83	WOMBAT-PK	CHEMBL
Cytochrome P450 2C9	Enzyme	P11712	CP2C9_HUMAN		EC50	5.30	WOMBAT-PK
Aldose reductase	Enzyme	P15121	ALDR_HUMAN		IC50	4.11	CHEMBL
Aldo-keto reductase family 1 member C1	Enzyme	Q04828	AK1C1_HUMAN		Ki	6.09	CHEMBL
Aldo-keto reductase family 1 member C2	Enzyme	P52895	AK1C2_HUMAN		Ki	6.66	CHEMBL
Aldo-keto reductase family 1 member C3	Enzyme	P42330	AK1C3_HUMAN		Ki	6.52	CHEMBL
Myeloperoxidase	Enzyme	P05164	PERM_HUMAN		IC50	6.01	CHEMBL
Transient receptor potential cation channel subfamily A member 1	Ion channel	O75762	TRPA1_HUMAN		EC50	4.80	CHEMBL
Aldo-keto reductase family 1 member B10	Enzyme	O60218	AK1BA_HUMAN		IC50	5.80	CHEMBL
Nicotinate phosphoribosyltransferase	Enzyme	Q6XQN6	PNCB_HUMAN		Ki	10.30	CHEMBL
Dihydrofolate reductase	Enzyme	P00374	DYR_HUMAN		Ki	4.14	CHEMBL
Acetylcholinesterase	Enzyme		ACES_TORCA		IC50	5.21	CHEMBL
NACHT, LRR and PYD domains-containing protein 3	Unclassified		NLRP3_MOUSE		IC50	4.60	CHEMBL

External reference:

ID	Source
4019082	VUID
N0000147343	NUI
D00151	KEGG_DRUG
4019082	VANDF
C0025152	UMLSCUI
CHEBI:6717	CHEBI
ID8	PDB_CHEM_ID
CHEMBL686	ChEMBL_ID
DB00784	DRUGBANK_ID
D008528	MESH_DESCRIPTOR_UI
4044	PUBCHEM_CID
2593	IUPHAR_LIGAND_ID
1494	INN_ID
367589PJ2C	UNII
257844	RXNORM
5034	MMSL
91405	MMSL
d00285	MMSL
001578	NDDF
116727007	SNOMEDCT_US
34364009	SNOMEDCT_US
387185008	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	0276-0509	CAPSULE	250 mg	ORAL	ANDA	26 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	0276-0509	CAPSULE	250 mg	ORAL	ANDA	26 sections
Mefenamic acid	HUMAN PRESCRIPTION DRUG LABEL	1	42571-258	CAPSULE	250 mg	ORAL	ANDA	25 sections
Mefenamic acid	HUMAN PRESCRIPTION DRUG LABEL	1	42571-258	CAPSULE	250 mg	ORAL	ANDA	25 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	62250-677	CAPSULE	250 mg	ORAL	ANDA	27 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	62250-677	CAPSULE	250 mg	ORAL	ANDA	27 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	64380-790	CAPSULE	250 mg	ORAL	ANDA	25 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	64380-790	CAPSULE	250 mg	ORAL	ANDA	25 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	68180-185	CAPSULE	250 mg	ORAL	ANDA	23 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	68180-185	CAPSULE	250 mg	ORAL	ANDA	23 sections
Mefenamic Acid	HUMAN PRESCRIPTION DRUG LABEL	1	80425-0306	CAPSULE	250 mg	ORAL	ANDA	12 sections