Tolfenamic acid: Difference between revisions

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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 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C14H12ClNO2
Molar mass	261.707 g/mol
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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VisualWikitext

Latest revision as of 17:10, 13 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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, Migrex and Tufnil for use in humans and Tolfedine for veterinary use in cats and dogs. This drug should not be confused with Tolmetin.

References

↑ ^1.0 ^1.1 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" Check |url= value (help). J. Chem. Soc., Perkin Trans. 2 (10): 1443–1447. doi:10.1039/P29890001443.

External links

Tolfenamic acid information (Diseases Database)

Template:GABAAR PAMs

Template:Musculoskeletal-drug-stub

[Andersen-1] 1.0 ^1.1 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" Check |url= value (help). J. Chem. Soc., Perkin Trans. 2 (10): 1443–1447. doi:10.1039/P29890001443.

[1]

@@ Line 1: / Line 1: @@
-{{Drugbox|
+{{Drugbox
-|IUPAC_name = 2-[(3-chloro-2-methylphenyl)amino]benzoic acid)."<ref>Kim Vilbour Andersen, Sine Larsen, Børge Alhede, Niels Gelting and Ole Buchardt [http://www.rsc.org/Publishing/Journals/P2/article.asp?doi=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, 1989, 1443 - 1447, DOI:10.1039/P29890001443</ref>
+| Verifiedfields = changed
-| image=Tolfenamic_Acid.png
+| verifiedrevid = 470611500
-| width= 220
+| IUPAC_name = 2-[(3-chloro-2-methylphenyl)amino]benzoic acid)<ref name="Andersen">{{cite journal | author = Kim Vilbour Andersen, Sine Larsen, Børge Alhede, Niels Gelting and Ole Buchardt | url = http://www.rsc.org/Publishing/Journals/P2/article.asp?doi = P29890001443 | title = Characterization of two polymorphic forms of tolfenamic acid, N-(2-methyl-3-chlorophenyl)anthranilic acid: their crystal structures and relative stabilities | journal = J. Chem. Soc., Perkin Trans. 2 | year = 1989 | issue = 10 | pages = 1443–1447 | doi = 10.1039/P29890001443}}</ref>
-| CAS_number= 13710-19-5
+| image = Tolenamic acid Wiki Str.png
-| ATC_prefix=
+| width = 220
-| ATC_suffix=
-| ATC_supplemental=
+<!--Clinical data-->
-| PubChem= 5507
+| tradename =
-| DrugBank=
+| Drugs.com = {{drugs.com|international|tolfenamic-acid}}
+| routes_of_administration = oral
+| legal_AU = S4
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 13710-19-5
+| ATC_prefix = M01
+| ATC_suffix = AG02
+| PubChem = 610479
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 530683
+| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII = 3G943U18KM
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D01183
+| ChEBI_Ref = {{ebicite|changed|EBI}}
+| ChEBI = 32243
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 121626
+<!--Chemical data-->
 | C=14 | H=12 | Cl=1 | N=1 | O=2
-| molecular_weight = 261.707
+| molecular_weight = 261.707 g/mol
-| bioavailability=
+| smiles = Clc2cccc(Nc1ccccc1C(=O)O)c2C
-| metabolism =
+| InChI = 1/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)
-| elimination_half-life=
+| InChIKey = YEZNLOUZAIOMLT-UHFFFAOYAX
-| excretion =
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| pregnancy_category =
+| StdInChI = 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)
-| legal_status =
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| routes_of_administration= oral
+| StdInChIKey = YEZNLOUZAIOMLT-UHFFFAOYSA-N
 }}
+__NOTOC__
-'''Tolfenamic acid''' (TA) is one of the class of [[Non-steroidal anti-inflammatory drug|non steroidal anti-inflammatory drugs]] ([[NSAID]]s). It is used to treat the symptoms of migraine.
+{{SI}}
+{{CMG}}
+== Overview ==
+'''Tolfenamic acid''' (TA) is one of the class of [[non-steroidal anti-inflammatory drug]]s (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)."<ref>S. Kaivola1, J. Parantainen, T. Österman and H. Timonen [http://www.blackwell-synergy.com/links/doi/10.1046%2Fj.1468-2982.1983.0301031.x Hangover headache and prostaglandins: Prophylactic treatment with tolfenamic acid] ''Cephalalgia'' Volume 3 Page 31  - March 1983 doi:10.1046/j.1468-2982.1983.0301031.x</ref>
+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)."<ref name="Andersen"/>
 == Commercial names ==
-Commercial names for tolfenamic acid include:
+Commercial names for tolfenamic acid include Clotam Rapid, Migrex and Tufnil for use in humans and Tolfedine for veterinary use in cats and dogs. This drug should not be confused with [[Tolmetin]].
-*[http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?DocumentID=449  Clotam Rapid]
+== References ==
+{{Reflist|2}}
 == External links ==
-*[http://www.diseasesdatabase.com/ddb31603.htm Tolfenamic acid information]
+*[http://www.diseasesdatabase.com/ddb31603.htm Tolfenamic acid information] (Diseases Database)
-== References ==
-<references/>
-{{NSAIDs}}
 {{Anti-inflammatory and antirheumatic products}}
+{{GABAAR PAMs}}
+{{Serotonergics}}
+[[Category:drug]]
 [[Category:Non-steroidal anti-inflammatory drugs]]
 [[Category:Antipyretics]]
 [[Category:Analgesics]]
-[[Category:Benzoic acids]]
+[[Category:Organochlorides]]
+[[Category:Anthranilic acids]]
-{{pharma-stub}}
+[[Category:GABAA receptor positive allosteric modulators]]
-[[de:Tolfenaminsäure]]
+{{musculoskeletal-drug-stub}}
-{{WikiDoc Sources}}

v t e 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.

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)^[1]
CAS Number	13710-19-5^N
PubChem CID	610479
ChemSpider	530683^Y
UNII	3G943U18KM
KEGG	D01183^Y
ChEBI	CHEBI:32243^N
ChEMBL	ChEMBL121626^Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₄H₁₂ClNO₂
Molar mass	261.707 g/mol
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)^Y Key:YEZNLOUZAIOMLT-UHFFFAOYSA-N^Y
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