Bucetin

Bucetin
Clinical data
ATC code	N02BE04 (WHO) ;
Identifiers
	IUPAC name N-(4-Ethoxyphenyl)-3-hydroxybutanamide;
CAS Number	1083-57-4 ;
PubChem CID	14130;
ChemSpider	13507;
UNII	6M7CVQ8PF8;
ChEMBL	ChEMBL1697856;
CompTox Dashboard (EPA)	DTXSID6020721 ;
ECHA InfoCard	100.012.827
Chemical and physical data
Formula	C12H17NO3
Molar mass	223.272 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Nc1ccc(OCC)cc1)CC(O)C;
	InChI InChI=1S/C12H17NO3/c1-3-16-11-6-4-10(5-7-11)13-12(15)8-9(2)14/h4-7,9,14H,3,8H2,1-2H3,(H,13,15); Key:LIAWQASKBFCRNR-UHFFFAOYSA-N;

Bucetin (INN, BAN) is an analgesic and antipyretic that is no longer marketed.^[1]^[2] Chemically, it is similar to phenacetin with which it shares the risk of carcinogenesis.^[3] Bucetin was withdrawn from use in 1986 due to renal toxicity.^[4]

References

^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 184–. ISBN 978-1-4757-2085-3.
^ "WHOCC - ATC/DDD Index". WHO Collaborating Centre for Drug Statistics Methodology. December 19, 2013.
^ Togei K, Sano N, Maeda T, Shibata M, Otsuka H (November 1987). "Carcinogenicity of bucetin in (C57BL/6 X C3H)F1 mice". Journal of the National Cancer Institute. 79 (5): 1151–8. doi:10.1093/jnci/79.5.1151. PMID 3479641.
^ Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Drug Information Journal. 35: 293–317. doi:10.1177/009286150103500134. S2CID 73036562.

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 184–. ISBN 978-1-4757-2085-3.

[2] "WHOCC - ATC/DDD Index". WHO Collaborating Centre for Drug Statistics Methodology. December 19, 2013.

[3] Togei K, Sano N, Maeda T, Shibata M, Otsuka H (November 1987). "Carcinogenicity of bucetin in (C57BL/6 X C3H)F1 mice". Journal of the National Cancer Institute. 79 (5): 1151–8. doi:10.1093/jnci/79.5.1151. PMID 3479641.

[4] Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Drug Information Journal. 35: 293–317. doi:10.1177/009286150103500134. S2CID 73036562.

[1]

[2]

[3]

[4]

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 Meloxicam/rizatriptan Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
category commons portal

Clinical data

ATC code	N02BE04 (WHO)
Identifiers
IUPAC name N-(4-Ethoxyphenyl)-3-hydroxybutanamide
CAS Number	1083-57-4^Y
PubChem CID	14130
ChemSpider	13507
UNII	6M7CVQ8PF8
ChEMBL	ChEMBL1697856
CompTox Dashboard (EPA)	DTXSID6020721
ECHA InfoCard	100.012.827
Chemical and physical data
Formula	C₁₂H₁₇NO₃
Molar mass	223.272 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(Nc1ccc(OCC)cc1)CC(O)C
InChI InChI=1S/C12H17NO3/c1-3-16-11-6-4-10(5-7-11)13-12(15)8-9(2)14/h4-7,9,14H,3,8H2,1-2H3,(H,13,15) Key:LIAWQASKBFCRNR-UHFFFAOYSA-N

Bucetin

See also

References