Oxyphenbutazone

Oxyphenbutazone
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M01AA03 (WHO) M02AA04 (WHO) S01BC02 (WHO);
Legal status
Legal status	AU: Withdrawn; UK: Withdrawn; US: Withdrawn;
Identifiers
	IUPAC name (RS)-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione;
CAS Number	129-20-4 ;
PubChem CID	104811;
DrugBank	DB03585 ;
ChemSpider	94610 ;
UNII	A7D84513GV;
KEGG	D08324 ;
ChEBI	CHEBI:76258 ;
ChEMBL	ChEMBL1228 ;
CompTox Dashboard (EPA)	DTXSID1045291 ;
ECHA InfoCard	100.004.489
Chemical and physical data
Formula	C19H20N2O3
Molar mass	324.379 g/mol g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O;
	InChI InChI=1S/C19H20N2O3.H2O/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15;/h4-8,10-13,17,22H,2-3,9H2,1H3;1H2 ; Key:CNDQSXOVEQXJOE-UHFFFAOYSA-N ;
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Oxyphenbutazone is a nonsteroidal anti-inflammatory drug (NSAID).^[1] It is a metabolite of phenylbutazone.^[2]

It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and Stevens–Johnson syndrome.^[3]^[4]

References

^ Singh, N.; Jabeen, T.; Somvanshi, R. K.; Sharma, S.; Dey, S.; Singh, T. P. (2004). "Phospholipase A2as a Target Protein for Nonsteroidal Anti-Inflammatory Drugs (NSAIDs): Crystal Structure of the Complex Formed between Phospholipase A2and Oxyphenbutazone at 1.6 Å Resolution†". Biochemistry. 43 (46): 14577–14583. doi:10.1021/bi0483561. PMID 15544328.
^ Matthews, N. S.; Peck, K. E.; Taylor, T. S.; Mealey, K. L. (2001). "Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys". American journal of veterinary research. 62 (5): 673–675. PMID 11341383.
^ Fung, M.; Thornton, A.; Mybeck, K.; Wu, J. H.-h.; Hornbuckle, K.; Muniz, E. (1 January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Therapeutic Innovation & Regulatory Science. 35 (1): 293–317. doi:10.1177/009286150103500134.
^ Biron, P (15 May 1986). "Withdrawal of oxyphenbutazone: what about phenylbutazone?". Canadian Medical Association Journal. 134 (10): 1119–20. PMC 1491052. PMID 3697857.

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[1] Singh, N.; Jabeen, T.; Somvanshi, R. K.; Sharma, S.; Dey, S.; Singh, T. P. (2004). "Phospholipase A2as a Target Protein for Nonsteroidal Anti-Inflammatory Drugs (NSAIDs): Crystal Structure of the Complex Formed between Phospholipase A2and Oxyphenbutazone at 1.6 Å Resolution†". Biochemistry. 43 (46): 14577–14583. doi:10.1021/bi0483561. PMID 15544328.

[2] Matthews, N. S.; Peck, K. E.; Taylor, T. S.; Mealey, K. L. (2001). "Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys". American journal of veterinary research. 62 (5): 673–675. PMID 11341383.

[Fung-2001-3] Fung, M.; Thornton, A.; Mybeck, K.; Wu, J. H.-h.; Hornbuckle, K.; Muniz, E. (1 January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Therapeutic Innovation & Regulatory Science. 35 (1): 293–317. doi:10.1177/009286150103500134.

[4] Biron, P (15 May 1986). "Withdrawal of oxyphenbutazone: what about phenylbutazone?". Canadian Medical Association Journal. 134 (10): 1119–20. PMC 1491052. PMID 3697857.

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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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