Tolfenamic acid

Tolfenamic acid is a member of the anthranilic acid derivatives (or fenamate) class of NSAID drugs.^[3] Like other members of the class, it is a COX inhibitor and prevents formation of prostaglandins.^[4]

Tolfenamic acid

Clinical data
Trade names	Clotam, Clotan, Tufnil, Migea
AHFS/Drugs.com	International Drug Names
Routes of administration	By mouth
ATC code	M01AG02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) EU: Rx-only[1]
Identifiers
IUPAC name 2-[(3-chloro-2-methylphenyl)amino]benzoic acid)[2]
CAS Number	13710-19-5 N
PubChem CID	610479
DrugBank	DB09216 Y
ChemSpider	530683 Y
UNII	3G943U18KM
KEGG	D01183 Y
ChEBI	CHEBI:32243 N
ChEMBL	ChEMBL121626 Y
CompTox Dashboard (EPA)	DTXSID1045409
ECHA InfoCard	100.033.862
Chemical and physical data
Formula	C14H12ClNO2
Molar mass	261.71 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc2cccc(Nc1ccccc1C(=O)O)c2C
InChI InChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18) Y Key:YEZNLOUZAIOMLT-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

It is used in the UK as a treatment for migraine.^[5][6] It is generally not available in the US.^[4] It is available in some Asian, Latin American and European countries as a generic drug for humans and for animals.^[7]

Medical uses

Tolfenamic acid finds utility in the prevention and treatment of conditions associated with pain and inflammation.^[8][9] However, despite its efficacy when administered intramuscularly, subcutaneously, or orally,^[10] TFA-based drugs have not yet gained approval in the United States and some other countries due to the significant number of reported side effects.^[11][12]

Chemistry

Tolfenamic acid, belonging to the pharmacological group of fenamates, possesses a chemical structure typical of anthranilic acid derivatives. In this structure, one of the hydrogen atoms of the nitro group is substituted by a benzene ring featuring a methyl group and a chlorine atom at the ortho- and meta- positions, respectively.^[13]

Nine forms of tolfenamic acid have been identified, some of which are determined by conformational states.^[14][15][16] These polymorphic forms exhibit variations in the spatial arrangement within the unit cell and in the values of the C-N(H)-C-C angle.^[16] This diversity in solid forms makes TFA an attractive candidate for modification and utilization in medical applications.

History

It was discovered by scientists at Medica Pharmaceutical Company in Finland.^[3]

Research

Tolfenamic acid demonstrates the ability to inhibit the growth of cancer cells in the pancreas, sigmoid colon, and rectum.^[17]