Flufenamic acid

Flufenamic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth, topical
ATC code	M01AG03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only);
Pharmacokinetic data
Protein binding	extensively
Metabolism	Hydroxylation, glucuronidation
Elimination half-life	~3 h
Excretion	50% urine, 36% feces
Identifiers
	IUPAC name 2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid;
CAS Number	530-78-9 ;
PubChem CID	3371;
IUPHAR/BPS	2447;
DrugBank	DB02266 ;
ChemSpider	3254 ;
UNII	60GCX7Y6BH;
KEGG	D01581 ;
ChEBI	CHEBI:42638 ;
ChEMBL	ChEMBL23588 ;
CompTox Dashboard (EPA)	DTXSID7023063 ;
ECHA InfoCard	100.007.723
Chemical and physical data
Formula	C14H10F3NO2
Molar mass	281.234 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	124 to 125 °C (255 to 257 °F) resolidification and remelting at 134°C to 136°C
Solubility in water	Practically insoluble in water; soluble in ethanol, chloroform and diethyl ether mg/mL (20 °C)
	SMILES FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)O;
	InChI InChI=1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20) ; Key:LPEPZBJOKDYZAD-UHFFFAOYSA-N ;
	(verify)

Flufenamic acid (FFA) is a member of the anthranilic acid derivatives (or fenamate) class of nonsteroidal anti-inflammatory drugs (NSAIDs).^: 718 Like other members of the class, it is a cyclooxygenase (COX) inhibitor, preventing the formation of prostaglandins. FFA is known to bind to and reduce the activity of prostaglandin F synthase and activate TRPC6.

Scientists led by Claude Winder from Parke-Davis invented FFA in 1963, along with fellow members of the class, mefenamic acid in 1961 and meclofenamic acid in 1964.^: 718

Although flufenamic acid was at one time informally referred to as "Fluffy" (see history cache), this pet name could also refer to flufenoxine.

Clinical data


AHFS/Drugs.com	International Drug Names
Routes of administration	By mouth, topical
ATC code	M01AG03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Protein binding	extensively
Metabolism	Hydroxylation, glucuronidation
Elimination half-life	~3 h
Excretion	50% urine, 36% feces
Identifiers
IUPAC name 2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid
CAS Number	530-78-9^Y
PubChem CID	3371
IUPHAR/BPS	2447
DrugBank	DB02266^Y
ChemSpider	3254^Y
UNII	60GCX7Y6BH
KEGG	D01581^Y
ChEBI	CHEBI:42638^Y
ChEMBL	ChEMBL23588^Y
CompTox Dashboard (EPA)	DTXSID7023063
ECHA InfoCard	100.007.723
Chemical and physical data
Formula	C₁₄H₁₀F₃NO₂
Molar mass	281.234 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	124 to 125 °C (255 to 257 °F) resolidification and remelting at 134°C to 136°C
Solubility in water	Practically insoluble in water; soluble in ethanol, chloroform and diethyl ether mg/mL (20 °C)
SMILES FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)O
InChI InChI=1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20)^Y Key:LPEPZBJOKDYZAD-UHFFFAOYSA-N^Y
(verify)