Fenamic acid

Fenamic acid

IUPAC name 2-(phenylamino)benzoic acid
Other names N-phenylanthranilic acid
Identifiers
CAS number	91-40-7^Y
PubChem	4386
ChEMBL	CHEMBL23832^N
Jmol-3D images	Image 1
SMILES C1=CC=C(C=C1)NC2=CC=CC=C2C(=O)O
Properties
Molecular formula	C₁₃H₁₁NO₂
Molar mass	213.23 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Fenamic acid is a molecule which serves as a parent structure for several non-steroidal anti-inflammatory drugs, including mefenamic acid, tolfenamic acid, flufenamic acid, and meclofenamic acid.

This compound may be synthesized by the reaction of 2-chlorobenzoic acid and aniline, with base and copper oxide catalyst in the Goldberg reaction.^[1]

The self-condensation of fenamic acid yields acridone.^[1]

References

^ ^a ^b C. F. H. Allen and G. H. W. McKee (1943), "Acridone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0015 ; Coll. Vol. 2: 15

Anti-inflammatory products (M01A)

Pyrazolidine/Butylpyrazolidines

Ampyrone • Clofezone • Kebuzone • Metamizole • Mofebutazone • Oxyphenbutazone • Phenazone • Phenylbutazone • Sulfinpyrazone • Feprazone •

Acetic acid derivatives
and related substances

Aceclofenac • Acemetacin • Alclofenac • Bromfenac • Bumadizone • Bufexamac • Diclofenac • Difenpiramide • Etodolac • Fentiazac • Indometacin • Ketorolac • Lonazolac • Oxametacin • Proglumetacin • Sulindac • Tolmetin • Zomepirac • Amfenac

Oxicams

Ampiroxicam • Droxicam • Lornoxicam • Meloxicam • Piroxicam • Tenoxicam

Propionic acid derivatives

Alminoprofen • Benoxaprofen • Dexibuprofen • Dexketoprofen • Fenbufen • Fenoprofen • Flunoxaprofen • Flurbiprofen • Ibuprofen • Ibuproxam • Indoprofen • Ketoprofen • Naproxen • Oxaprozin • Pirprofen • Suprofen • Tiaprofenic acid

Fenamates

Flufenamic acid • Meclofenamic acid • Mefenamic acid • Tolfenamic acid • Niflumic acid • Morniflumate • Azapropazone •

Coxibs

Celecoxib • Etoricoxib • Lumiracoxib • Parecoxib • Rofecoxib • Valdecoxib

Other

Nabumetone • Glucosamine • Benzydamine • Glycosaminoglycan • Magnesium salicylate • Proquazone • Superoxide dismutase/Orgotein • Nimesulide • Diacerein • Tenidap • Oxaceprol • Chondroitin sulfate

M: MUS, DF+DRCT

anat (h/n, u, t/d, a/p, l)/phys/devp/hist

noco(m, s, c)/cong(d)/tumr, sysi/epon, injr

proc, drug (M1A/3)

Non-steroidal anti-inflammatory drug (NSAID) products (primarily M01A and M02A, also N02BA)

Salicylates	Aspirin (acetylsalicylic acid) • Aloxiprin • Benorylate • Diflunisal • Ethenzamide • Magnesium salicylate • Methyl salicylate • Salsalate • Salicin • Salicylamide • Sodium salicylate

Arylalkanoic acids	Diclofenac • Aceclofenac • Acemetacin • Alclofenac • Bromfenac • Etodolac • Indometacin • Indometacin farnesil • Nabumetone • Oxametacin • Proglumetacin • Sulindac • Tolmetin

2-Arylpropionic acids (profens)	Ibuprofen • Alminoprofen • Benoxaprofen • Carprofen • Dexibuprofen • Dexketoprofen • Fenbufen • Fenoprofen • Flunoxaprofen • Flurbiprofen • Ibuproxam • Indoprofen^† • Ketoprofen • Ketorolac • Loxoprofen • Miroprofen • Naproxen • Oxaprozin • Pirprofen • Suprofen • Tarenflurbil • Tiaprofenic acid

N-Arylanthranilic acids (fenamic acids)	Mefenamic acid • Flufenamic acid • Meclofenamic acid • Tolfenamic acid

Pyrazolidine derivatives	Phenylbutazone • Ampyrone • Azapropazone • Clofezone • Kebuzone • Metamizole • Mofebutazone • Oxyphenbutazone • Phenazone • Sulfinpyrazone

Oxicams	Piroxicam • Droxicam • Lornoxicam • Meloxicam • Tenoxicam • Ampiroxicam

COX -2 inhibitors	Celecoxib • Deracoxib^‡ • Etoricoxib • Firocoxib^‡ • Lumiracoxib^† • Parecoxib • Rofecoxib^† • Valdecoxib^†

Sulfonanilides	Nimesulide

Topically used products	Bendazac • Diclofenac • Etofenamate • Felbinac • Flurbiprofen • Ibuprofen • Indometacin • Ketoprofen • Naproxen • Piroxicam • Suprofen

COX-inhibiting nitric oxide donators	Naproxcinod

Others	Fluproquazone

Items listed in bold indicate initially developed compounds of specific groups. ^†Withdrawn drugs. ^‡Veterinary use medications.