Tolfenamic acid

Tolfenamic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	oral
ATC code	M01AG02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only);
Identifiers
	IUPAC name 2-[(3-chloro-2-methylphenyl)amino]benzoic acid);
CAS Number	13710-19-5 ;
PubChem CID	610479;
ChemSpider	530683 ;
UNII	3G943U18KM;
KEGG	D01183 ;
ChEBI	CHEBI:32243 ;
ChEMBL	ChEMBL121626 ;
CompTox Dashboard (EPA)	DTXSID1045409 ;
ECHA InfoCard	100.033.862
Chemical and physical data
Formula	C14H12ClNO2
Molar mass	261.707 g/mol 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) ; Key:YEZNLOUZAIOMLT-UHFFFAOYSA-N ;
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Tolfenamic acid (TA) is one of the class of non-steroidal anti-inflammatory drugs (NSAIDs). It is used to treat the symptoms of migraine.

Other possible uses

A study concludes, "TA was found significantly better than placebo in the subjective evaluation of drug efficacy (p<0.001) and in reducing the reported hangover symptoms in general (p < 0.01). In the TA group, significantly lower symptom scores were obtained for headache (p<0.01), and for nausea, vomiting, irritation, tremor, thirst and dryness of mouth (all p < 0.05)."^[1]

Commercial names

Commercial names for tolfenamic acid include Clotam Rapid and Tufnil for use in humans and Tolfedine for veterinary use in cats and dogs. This drug should not be confused with Tolmetin.

References

^ ^a ^b Kim Vilbour Andersen, Sine Larsen, Børge Alhede, Niels Gelting and Ole Buchardt (1989). = P29890001443 "Characterization of two polymorphic forms of tolfenamic acid, N-(2-methyl-3-chlorophenyl)anthranilic acid: their crystal structures and relative stabilities". J. Chem. Soc., Perkin Trans. 2 (10): 1443–1447. doi:10.1039/P29890001443. {{cite journal}}: Check |url= value (help)CS1 maint: multiple names: authors list (link)

External links

Tolfenamic acid information (Diseases Database)

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[Andersen-1] Kim Vilbour Andersen, Sine Larsen, Børge Alhede, Niels Gelting and Ole Buchardt (1989). = P29890001443 "Characterization of two polymorphic forms of tolfenamic acid, N-(2-methyl-3-chlorophenyl)anthranilic acid: their crystal structures and relative stabilities". J. Chem. Soc., Perkin Trans. 2 (10): 1443–1447. doi:10.1039/P29890001443. {{cite journal}}: Check |url= value (help)CS1 maint: multiple names: authors list (link)

[1]

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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