Ethenzamide

Ethenzamide
Clinical data
ATC code	N02BA07 (WHO) ;
Identifiers
	IUPAC name 2-ethoxybenzamide;
CAS Number	938-73-8 ;
PubChem CID	3282;
ChemSpider	3167 ;
UNII	L929ZCK4BF;
KEGG	D01466 ;
ChEMBL	ChEMBL1483877;
CompTox Dashboard (EPA)	DTXSID4020581 ;
ECHA InfoCard	100.012.133
Chemical and physical data
Formula	C9H11NO2
Molar mass	165.192 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1ccccc1OCC)N;
	InChI InChI=1S/C9H11NO2/c1-2-12-8-6-4-3-5-7(8)9(10)11/h3-6H,2H2,1H3,(H2,10,11) ; Key:SBNKFTQSBPKMBZ-UHFFFAOYSA-N ;
	(verify)

Ethenzamide (2-ethoxybenzamide) is a common analgesic and anti-inflammatory drug that is used for the relief of fever, headaches, and other minor aches and pains.^[1]^[2] It is also an ingredient in numerous cold medications and many prescription analgesics.^[3] It is used as an over-the-counter drug in Japan, often in combination with caffeine and acetaminophen, where it is marketed for uses including toothache, menstrual cramps, headache, and fever.^[4]

It is metabolized in vivo into salicylamide.^[5]

References

^ Darias V, Bravo L, Abdallah SS, Sánchez Mateo CC, Expósito-Orta MA, Lissavetsky J, Manzanares J (February 1992). "Synthesis and preliminary pharmacological study of thiophene analogues of the antipyretic and analgesic agent ethenzamide". Archiv der Pharmazie. 325 (2): 83–7. doi:10.1002/ardp.19923250206. PMID 1605721. S2CID 28098596.
^ Wang PJ, Guo HR (2004). "Frequent analgesics consumption in migraineurs: Comparison between chronic and episodic migraineurs". The Journal of Headache and Pain. 5 (1): 30–35. doi:10.1007/s10194-004-0065-x. PMC 3452147.
^ ChemChart
^ "OTC Pain Relief Medicine in Japan". Life Abroad. Retrieved March 22, 2021.
^ "エテンザミド" [Ethenzamide] (in Japanese). Retrieved March 22, 2021.

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[1] Darias V, Bravo L, Abdallah SS, Sánchez Mateo CC, Expósito-Orta MA, Lissavetsky J, Manzanares J (February 1992). "Synthesis and preliminary pharmacological study of thiophene analogues of the antipyretic and analgesic agent ethenzamide". Archiv der Pharmazie. 325 (2): 83–7. doi:10.1002/ardp.19923250206. PMID 1605721. S2CID 28098596.

[2] Wang PJ, Guo HR (2004). "Frequent analgesics consumption in migraineurs: Comparison between chronic and episodic migraineurs". The Journal of Headache and Pain. 5 (1): 30–35. doi:10.1007/s10194-004-0065-x. PMC 3452147.

[3] ChemChart

[4] "OTC Pain Relief Medicine in Japan". Life Abroad. Retrieved March 22, 2021.

[5] "エテンザミド" [Ethenzamide] (in Japanese). Retrieved March 22, 2021.

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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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