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Legal status	AU: Withdrawn UK: Withdrawn US: Withdrawn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^Y
PubChem (CID)	104811
DrugBank	DB03585^Y
ChemSpider	94610^Y
UNII	A7D84513GV^Y
KEGG	D08324^Y
ChEBI	CHEBI:76258^N
ChEMBL	CHEMBL1228^N
Chemical and physical data
Formula	C₁₉H₂₀N₂O₃
Molar mass	324.379 g/mol
3D model (Jmol)	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^Y Key:CNDQSXOVEQXJOE-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Oxyphenbutazone is a non-steroidal 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It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and Stevens–Johnson syndrome.^[3]^[4]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?". CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne. 134 (10): 1119–20. PMC 1491052. PMID 3697857. CS1 maint: Missing pipe (link)

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 Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indomethacin Indomethacin 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^‡ 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.

Topical products for joint and muscular pain (M02)

Anti-inflammatory
preparations,
non-steroids

Pyrazolidines	Phenylbutazone Mofebutazone Clofezone Oxyphenbutazone

Acetic acid derivatives	Tolmetin Diclofenac Fentiazac

Other	Benzydamine Etofenamate Piroxicam Felbinac Bufexamac Ketoprofen Bendazac Naproxen Ibuprofen Feprazone Niflumic acid Meclofenamic acid Flurbiprofen Suxibuzone Indometacin Nifenazone

Capsaicin derivatives

Zucapsaicin

Other

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