Chemistry:Etofenamate

Etofenamate
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Topical (cream, gel, spray)
ATC code	M02AA06 (WHO) ;
Legal status
Legal status	In general: Over-the-counter (OTC);
Pharmacokinetic data
Protein binding	98–99%
Metabolites	Flufenamic acid, hydroxyl derivatives
Excretion	35% renal, mostly biliary
Identifiers
	IUPAC name 2-(2-hydroxyethoxy)ethyl 2-[ [3-(trifluoromethyl)phenyl]amino]benzoate;
CAS Number	30544-47-9 ;
PubChem CID	35375;
DrugBank	DB08984 ;
ChemSpider	32560 ;
UNII	KZF0XM66JC;
KEGG	D04102 ;
Chemical and physical data
Formula	C18H18F3NO4
Molar mass	369.340 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)OCCOCCO;
	InChI InChI=1S/C18H18F3NO4/c19-18(20,21)13-4-3-5-14(12-13)22-16-7-2-1-6-15(16)17(24)26-11-10-25-9-8-23/h1-7,12,22-23H,8-11H2 ; Key:XILVEPYQJIOVNB-UHFFFAOYSA-N ;
	(verify)

Short description: NSAID analgesic medication

Etofenamate is a nonsteroidal anti-inflammatory drug (NSAID) used for the treatment of joint and muscular pain.^[1] It is available for topical application as a cream, a gel or as a spray.

Etofenamate is acutely toxic if swallowed; it is also very toxic to aquatic life, with long lasting effects.^[2]^{[unreliable medical source?]}

References

↑ "[Use of topical non-steroidal anti-inflammatory drugs in aggravated and decompensated arthroses]" (in German). Wiener Medizinische Wochenschrift 149 (19–20): 546–7. 1999. PMID 10637963.
↑ "Etofenamate". PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/35375.

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[1] "[Use of topical non-steroidal anti-inflammatory drugs in aggravated and decompensated arthroses]" (in German). Wiener Medizinische Wochenschrift 149 (19–20): 546–7. 1999. PMID 10637963.

[2] "Etofenamate". PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/35375.

[1]

[2]

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.

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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Topical (cream, gel, spray)
ATC code	M02AA06 (WHO)
Legal status
Legal status	In general: Over-the-counter (OTC)
Pharmacokinetic data
Protein binding	98–99%
Metabolites	Flufenamic acid, hydroxyl derivatives
Excretion	35% renal, mostly biliary
Identifiers
IUPAC name 2-(2-hydroxyethoxy)ethyl 2-[ [3-(trifluoromethyl)phenyl]amino]benzoate
CAS Number	30544-47-9^Y
PubChem CID	35375
DrugBank	DB08984^Y
ChemSpider	32560^Y
UNII	KZF0XM66JC
KEGG	D04102^Y
Chemical and physical data
Formula	C₁₈H₁₈F₃NO₄
Molar mass	369.340 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)OCCOCCO
InChI InChI=1S/C18H18F3NO4/c19-18(20,21)13-4-3-5-14(12-13)22-16-7-2-1-6-15(16)17(24)26-11-10-25-9-8-23/h1-7,12,22-23H,8-11H2^Y Key:XILVEPYQJIOVNB-UHFFFAOYSA-N^Y
(verify)

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