Flufenamic acid

Flufenamic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	oral, 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 NSAID drugs^[1]^: 718 Like other members of the class, it is a COX inhibitor and prevents formation of prostaglandins.^[2] FFA is known to bind to and reduce the activity of prostaglandin F synthase and activate TRPC6.^[3]

It is not widely used in humans as it has a high rate (30-60%) of gastrointestinal side effects.^[4]^: 310 It is generally not available in the US.^[2] It is available in some Asian and European countries as a generic.^[5]

Scientists led by Claude Winder from Parke-Davis invented FFA in 1963, along with fellow members of the class, mefenamic acid in 1961 and meclofenamate sodium in 1964.^[1]^: 718

References

^ ^a ^b Whitehouse MW (2005). "Drugs to treat inflammation: a historical introduction". Current Medicinal Chemistry. 12 (25): 2931–42. doi:10.2174/092986705774462879. ISBN 9781608052073. PMID 16378496.
^ ^a ^b NIH LiverTox Database Mefenamic Acid Last updated June 23, 2015. Page accessed July 3, 2015. Quote: "(fenamates generally not available in the United States, such as tolfenamic acid and flufenamic acid)"
^ "Chemical–Gene Interaction Query: Flufenamic Acid (Homo sapiens)". Comparative Toxicogenomics Database. North Carolina State University. Retrieved 4 July 2015.
^ Aronson JK (2009). Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier. ISBN 978-0-08-093294-1.
^ "International listings for flufenamic acid". Drugs.com. Retrieved 3 July 2015.

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[Whitehouse-1] Whitehouse MW (2005). "Drugs to treat inflammation: a historical introduction". Current Medicinal Chemistry. 12 (25): 2931–42. doi:10.2174/092986705774462879. ISBN 9781608052073. PMID 16378496.

[LiverTox-2] NIH LiverTox Database Mefenamic Acid Last updated June 23, 2015. Page accessed July 3, 2015. Quote: "(fenamates generally not available in the United States, such as tolfenamic acid and flufenamic acid)"

[3] "Chemical–Gene Interaction Query: Flufenamic Acid (Homo sapiens)". Comparative Toxicogenomics Database. North Carolina State University. Retrieved 4 July 2015.

[4] Aronson JK (2009). Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier. ISBN 978-0-08-093294-1.

[5] "International listings for flufenamic acid". Drugs.com. Retrieved 3 July 2015.

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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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