Fenamic acid

Fenamic acid
Names
	IUPAC name 2-(phenylamino)benzoic acid
	Other names N-phenylanthranilic acid
Identifiers
CAS Number	91-40-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34756 ;
ChEMBL	ChEMBL23832 ;
ChemSpider	4233 ;
ECHA InfoCard	100.001.879
IUPHAR/BPS	4182;
PubChem CID	4386;
UNII	952VN06WBB ;
CompTox Dashboard (EPA)	DTXSID6059025 ;
	InChI InChI=1S/C13H11NO2/c15-13(16)11-8-4-5-9-12(11)14-10-6-2-1-3-7-10/h1-9,14H,(H,15,16) Key: ZWJINEZUASEZBH-UHFFFAOYSA-N ; InChI=1/C13H11NO2/c15-13(16)11-8-4-5-9-12(11)14-10-6-2-1-3-7-10/h1-9,14H,(H,15,16) Key: ZWJINEZUASEZBH-UHFFFAOYAQ;
	SMILES C1=CC=C(C=C1)NC2=CC=CC=C2C(=O)O;
Properties
Chemical formula	C13H11NO2
Molar mass	213.23 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Fenamic acid is an organic compound, which, especially in its ester form, is called fenamate.[1]^:458 serves as a parent structure for several nonsteroidal anti-inflammatory drugs (NSAIDs), including mefenamic acid, tolfenamic acid, flufenamic acid, and meclofenamic acid. These drugs are commonly referred to as "anthranilic acid derivatives" or "fenamates" because fenamic acid is a derivative of anthranilic acid.[2]^:235[3]^:17[2]

Fenamic acid can be synthesized from 2-chlorobenzoic acid and can be converted into acridone.[4]

References

Gupta, PK. Drug NomenclatureUnited States Adopted Names. Ch 27 in Remington: The Science and Practice of Pharmacy, Vol 1. Eds. David B. Troy, Paul Beringer. Lippincott Williams & Wilkins, 2006 ISBN 9780781746731
Sriram D, Yogeeswari P. Medicinal Chemistry, 2nd Edition. Pearson Education India, 2010. ISBN 9788131731444
Auburn University course material. Jack DeRuiter, Principles of Drug Action 2, Fall 2002 1: Non-Steroidal Antiinflammatory Drugs (NSAIDS)
C. F. H. Allen, G. H. W. McKee (1939). "Acridone". Organic Syntheses. 2: 6. doi:10.15227/orgsyn.019.0006.

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[1] Gupta, PK. Drug NomenclatureUnited States Adopted Names. Ch 27 in Remington: The Science and Practice of Pharmacy, Vol 1. Eds. David B. Troy, Paul Beringer. Lippincott Williams & Wilkins, 2006 ISBN 9780781746731

[Sriram-2] Sriram D, Yogeeswari P. Medicinal Chemistry, 2nd Edition. Pearson Education India, 2010. ISBN 9788131731444

[3] Auburn University course material. Jack DeRuiter, Principles of Drug Action 2, Fall 2002 1: Non-Steroidal Antiinflammatory Drugs (NSAIDS)

[4] C. F. H. Allen, G. H. W. McKee (1939). "Acridone". Organic Syntheses. 2: 6. doi:10.15227/orgsyn.019.0006.

Nonsteroidal 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 Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
Oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
N-Arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin
Coxibs	Apricoxib Celecoxib 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
Items listed in bold indicate initially developed compounds of specific groups. ^#WHO-EM ^†Withdrawn drugs. ^‡Veterinary use medications.