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Showing drug card for Oxyphenbutazone (DB03585)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2008-08-26 14:32:40
Primary Accession Number DB03585
Secondary Accession Number
  • EXPT02440
Name Oxyphenbutazone
Drug Type
  • Experimental
  • Small Molecule
  • Withdrawn
Description Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.
Synonyms
  1. 1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione
  2. 1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine
  3. 1-p-Hydroxyphenyl-2-phenyl-3,5-dioxo-4-N-butylpyrazolidine
  4. 3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl
  5. 4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione
  6. 4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione
  7. 4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine
  8. 4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione
  9. Hydroxyphenylbutazon
  10. OPB
  11. Ossifenbutazone [dcit]
  12. Oxifenbutazona [inn-spanish]
  13. Oxifenylbutazon
  14. Oxiphenbutazone
  15. Oxiphenbutazonum
  16. Oxyphenbutazonum [inn-latin]
  17. Oxyphenobutazone
  18. Oxyphenylbutazone
  19. P-hydroxyphenylbutazone
  20. P-oxyphenylbutazone
  21. Usaf Ge-14
Brand Names
  1. Aradinum
  2. Artroflog
  3. Butaflogin
  4. Butanora
  5. Butanova
  6. Butapirone
  7. Butazonic
  8. Butilene
  9. Californit
  10. Cinophen-n
  11. Crovaril
  12. Deflogin
  13. Etrozolidina
  14. Flamaril
  15. Flanaril
  16. Flegmostam
  17. Flogal
  18. Floghene
  19. Flogistin
  20. Flogitolo
  21. Flogodin
  22. Flogoril
  23. Flogostop
  24. Flopirina
  25. Frabel
  26. Genal
  27. Idrobutazina
  28. Infamil
  29. Infammil
  30. Ipabutona
  31. Iridil
  32. Isobutazina
  33. Isobutil
  34. Metabolite I
  35. Mysite
  36. Neo-farmadol
  37. Neofen
  38. Offitril
  39. Optimal
  40. Oxalid
  41. Oxazolidin
  42. Oxazolidin-geigy
  43. Oxazolioin
  44. Oxi-fenibutol
  45. Oxibutol
  46. Oxybuton
  47. Oxyphentamin
  48. Pirabutina
  49. Piraflogin
  50. Poliflogil
  51. Portoril
  52. Rapostan
  53. Remazin
  54. Reumox
  55. Reunabutal
  56. Rumapax
  57. Tandacote
  58. Tandalgesic
  59. Tandearil
  60. Tanderal
  61. Tanderil
  62. Telidac
  63. Telidal
  64. Tendearil
  65. Valioil
  66. Visubutina
Brand Mixtures Not Available
Chemical IUPAC Name 4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
Chemical Formula C19H20N2O3
Chemical Structure Structure
CAS Registry Number 129-20-4
InChI Identifier InChI=1/C19H20N2O3/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
InChI Key HFHZKZSRXITVMK-UHFFFAOYAY
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 4641 Link Image
PubChem Substance 10446442 Link Image
ChEBI ID Not Available
PharmGKB ID PA450750 Link Image
HET ID OPB Link Image
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Oxyphenbutazone Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 324.3737
Monoisotopic Molecular Weight 324.1474
State Solid
Melting Point 96 oC
Experimental Water Solubility 0.06 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 2.56e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.72 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP 2.79 Calculated using ALOGPS
Experimental LogS -3.73 [ADME Research, USCD]
Predicted LogS -3.10 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1Q7A Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES CCCC[C@@H]1C(=O)N(N(C1=O)C1=CC=C(O)C=C1)C1=CC=CC=C1
Canonical SMILES CCCCC1C(=O)N(N(C1=O)C1=CC=C(O)C=C1)C1=CC=CC=C1
Drug Category
  • Anti-Inflammatory Agents, Non-Steroidal
  • Phospholipase A2 Vrv-Pl-Viiia inhibitor
ATC Codes Not Available
AHFS Codes Not Available
Indication Not Available
Pharmacology Not Available
Mechanism of Action Not Available
Absorption Not Available
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions
Drug Interaction
Acenocoumarol The NSAID increases the anticoagulant effect
Alendronate Increased risk of gastric toxicity
Anisindione The NSAID increases the anticoagulant effect
Dicumarol The NSAID increases the anticoagulant effect
Ethotoin The NSAID increases the hydantoin effect
Fosphenytoin The NSAID increases the hydantoin effect
Mephenytoin The NSAID increases the hydantoin effect
Phenytoin The NSAID increases the hydantoin effect
Warfarin The NSAID increases the anticoagulant effect
Food Interactions
  • Take with food to reduce irritation.
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected Not Available
Targets
  1. Phospholipase A2 VRV-PL-VIIIa
Drug Target 1 [top]
Target 1 ID 2394
Target 1 Name Phospholipase A2 VRV-PL-VIIIa
Target 1 Synonyms
  1. DPLA2
  2. EC 3.1.1.4
  3. Phosphatidylcholine 2- acylhydrolase
Target 1 Gene Name Not Available
Target 1 Protein Sequence >Phospholipase A2 VRV-PL-VIIIa 
SLLEFGKMILEETGKLAIPSYSSYGCYCGWGGKGTPKDATDRCCFVHDCCYGNLPDCNPK
SDRYKYKRVNGAIVCEKGTSCENRICECDKAAAICFRQNLNTYSKKYMLYPDFLCKGELK
C
Target 1 Number of Residues 123
Target 1 Molecular Weight 13611
Target 1 Theoretical pI 8.06
Target 1 GO Classification
Function
binding
ion binding
cation binding
calcium ion binding
catalytic activity
hydrolase activity
hydrolase activity, acting on ester bonds
carboxylic ester hydrolase activity
lipase activity
phospholipase activity
phospholipase A2 activity
Process
physiological process
metabolism
primary metabolism
lipid metabolism
lipid catabolism
Component
Not Available
Target 1 General Function Involved in phospholipase A2 activity
Target 1 Specific Function PA2 catalyzes the calcium-dependent hydrolysis of the 2- acyl groups in 3-sn-phosphoglycerides. This toxin shows neurotoxic symptoms and damages vital organs such as lung, liver and kidney. Displays edema-inducing activities when injected into the foot pads of mice and induces necrosis of muscle cells when injected into the thigh muscle
Target 1 Pathways
Name SMPDB Link KEGG Link
Glycerophospholipid metabolism map00564 Link Image
Target 1 Reactions
  • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID P59071 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PA28_DABRP Link Image
Target 1 PDB ID 1Y38 Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Secreted protein
Target 1 Gene Sequence Not Available
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs Not Available
Target 1 General References
  1. Kasturi S, Gowda TV: Purification and characterization of a major phospholipase A2 from Russell's viper (Vipera russelli) venom. Toxicon. 1989;27(2):229-37. [PubMed Link Image]
  2. Gowda VT, Schmidt J, Middlebrook JL: Primary sequence determination of the most basic myonecrotic phospholipase A2 from the venom of Vipera russelli. Toxicon. 1994 Jun;32(6):665-73. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.