4-butyl-1,2-diphenylpyrazolidine-3,5-dione

• ChemBase ID: 691
• Molecular Formular: C19H20N2O2
• Molecular Mass: 308.3743
• Monoisotopic Mass: 308.15247789
• SMILES: O=C1N(N(C(=O)C1CCCC)c1ccccc1)c1ccccc1
• Canonical SMILES: CCCCC1C(=O)N(N(C1=O)c1ccccc1)c1ccccc1
• InChI: InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
• InChIKey: VYMDGNCVAMGZFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione
• IUPAC Traditional name: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione; phenylbutazone
• Brand Name: 'Esteve'; Alindor; Alka Butazolidin; Alkabutazona; Alqoverin; Ambene; Anerval; Anpuzone; Antadol; Anuspiramin; Apo-Phenylbutazone; Arthrizon; Artizin; Artrizin; Artrizone; Artropan; Azdid; Azobutyl; Azolid; B.T.Z.; Benzone; Betazed; Bizolin; Bizolin 200; Bunetzone; Busone; Buta Phen; Butacompren; Butacote; Butadion; Butadiona; Butadione; Butagesic; Butalgina; Butalidon; Butaluy; Butapirazol; Butapirazole; Butapyrazole; Butarecbon; Butartril; Butartrina; Butatron; Butazina; Butazolidin; Butazolidine; Butazona; Butazone; Bute; Butidiona; Butiwas-Simple; Butone; Butoz; Butylpyrin; Buvetzone; Buzon; Chembutazone; Cotylbutazone; Digibutina; Diossidone; Diozol; Diphebuzol; Diphenylbutazone; Ecobutazone; Elmedal; Equi Bute; Equipalazone; Eributazone; Exrheudon N; Febuzina; Fenartil; Fenibutal; Fenibutasan; Fenibutazona; Fenibutol; Fenilbutazona; Fenilbutina; Fenilbutine; Fenilidina; Fenotone; Fenylbutazon; Ia-But; Intalbut; Intrabutazone; Intrazone; Ipsoflame; Kadol; Lingel; Malgesic; Mepha-Butazon; Mephabutazon; Mephabutazone; Merizone; Nadazone; Nadozone; Neo-Zoline; Novophenyl; Phebuzin; Phebuzine; Phenbutazol; Phenbutazone; Phenopyrine; Phenyl-Mobuzon; Phenylbutaz; Phenylbutazonum; Phenyzene; Phenyzone; Pirarreumol "B"; Pirarreumol B; Praecirheumin; Pyrabutol; Pyrazolidin; Rectofasa; Reudo; Reudox; Reumasyl; Reumazin; Reumazol; Reumune; Reumuzol; Reupolar; Robizon-V; Robizone; Robizone-V; Rubatone; Scanbutazone; Schemergin; Shigrodin; Tazone; Tencodyne; Tetnor; Tevcodyne; Therazone; Ticinil; Todalgil; Usaf Ge-15; Uzone; VAC-10; Wescozone; Zolaphen; Zolidinum
• Synonyms: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione; 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine; Alindor; Alkazone; Antadol; Benzone; Betazed; Diphebuzol; Flexazone; Robizone; Shigrodin; Tencodyne; Uzone; VAC-10; Zolaphen; Phenylbutazone; Phenbutazone; Diphenylbutazone; Butapirazole; Butadion; Butacote; Butalidon; Fenylbutazon; 4-Butyl-1,2-diphenyl-3,5-pyrazolidinedione; Phenylbutazone; 4-BUTYL-1,2-DIPHENYL-PYRAZOLIDINE-3,5-DIONE; Bute; Butazolidin; Butatron; 苯基丁氮酮; Phenylbutazone

Database IDs

• CAS Number: 50-33-9
• EC Number: 200-029-0
• MDL Number: MFCD00005500
• Beilstein Number: 290080
• Merck Index: 147277
• PubChem SID: 24277729; 160964154; 46507038
• PubChem CID: 4781
• CHEBI ID: 48574
• ATC CODE: M01AA01; M02AA01
• CHEMBL: 101
• Chemspider ID: 4617
• DrugBank ID: DB00812
• KEGG ID: D00510
• Unique Ingredient Identifier: GN5P7K3T8S
• Wikipedia Title: Phenylbutazone

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.1349697
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.6229165
• LogD (pH = 7.4): 2.2602339
• Log P: 4.135798
• Molar Refractivity: 88.7583 cm^3
• Polarizability: 34.466145 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.81
• LOG S: -3.33
• Solubility (Water): 1.44e-01 g/l

PROPERTIES

Physical Property

• Solubility: 47.5 mg/L; Chloroform; Methanol
• Apperance: Off-Whtie Solid
• Melting Point: 102-105°C; 105 °C; 105-108°C; 106 - 108°C; 106-108 °C(lit.)
• Hydrophobicity(logP): 3.385; 3.7

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: UQ8225000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 20/21/22-36/37/38; 22-36-40-63; R:22-36
• Safety Statements: 26-36/37; S:26-36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H315-H319-H332-H335; H301-H319-H351-H361
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338; P280H-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Legal Status: rx-only
• Gene Information: human ... CYP2C9(1559), PTGIS(5740), PTGS2(5743)
• Mechanism of Action: Prostaglandin antagonist

Product Information

• Purity: ≥99.0%; 98%; null%
• Grade: SAJ special grade
• Salt Data: Free Base
• Application(s): Analgesic; Antiinflammatory, esp. antirheumatic; Antipyretic; Use limited due to toxicity
• Empirical Formula (Hill Notation): C19H20N2O2

DETAILS

DrugBank - DB00812

• Drug Groups: approved
• Description: A drug that has anti-inflammatory, antipyretic, and analgesic activities. It is especially effective in the treatment of ankylosing spondylitis. It also is useful in rheumatoid arthritis and Reiter's syndrome (investigational indication). Although phenylbutazone is effective in gouty arthritis, risk/benefit considerations indicate that this drug should not be employed for this disease. (From AMA Drug Evaluations Annual, 1994, p1822)
• Indication: For the treatment of backache and ankylosing spondylitis
• Pharmacology: Phenylbutazone is a synthetic, pyrazolone derivative. It is a nonhormonal anti-inflammatory, antipyretic compound useful in the management of inflammatory conditions. The apparent analgesic effect is probably related mainly to the compound's anti-inflammatory properties and arise from its ability to reduce production of prostaglandin H and prostacyclin. Prostaglandins act on a variety of cells such as vascular smooth muscle cells causing constriction or dilation, on platelets causing aggregation or disaggregation and on spinal neurons causing pain. Prostacylcin causes vascular constriction platelet disaggregation
• Toxicity: Oral, LD₅₀ = 238 mg/kg (mouse); Oral, LD₅₀ = 781 mg/kg (rabbit); Oral, LD₅₀ = 245 mg/kg (rat); Oral, LD₅₀ = 375 mg/kg (rat)
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

DrugBank - DB08343

Drug information: experimental

Selleck Chemicals - S1654

Research Area: Inflammation
Biological Activity:
Phenylbutazone(Butazolidin, Butatron) is used as a non-steroidal anti-inflammatory agent for the treatment of chronic pain, including the symptoms of arthritis. Its use is limited by such severe side effects as suppression of white blood cell production and aplastic anemia. [1]

Sigma Aldrich - P8386

Substrates
Non-steroidal anti-inflammatory compound; inhibitor of cyclooxygenase that is also a substrate for peroxidation by cyclooxygenase.

Toronto Research Chemicals - P319570

A non-steroidal anti-inflammatory compound. An inhibitor of cyclooxygenase that is also a substrate for peroxidation by cyclooxygenase.

REFERENCES

• http://en.wikipedia.org/wiki/Phenylbutazone
• Ali, S.L., Anal. Profiles Drug Subs., 11, 483 (1982)
• Hughes, M.F., et al.: Mol. Pharmacol., 34, 186 (1982)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1449A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 400C, (ir)
• Denss, R., Experientia, 1959, 15, 95, (synth)
• Mondelli, R. et al., Gazz. Chim. Ital., 1965, 95, 1371, (pmr)
• Locock, R.A. et al., J. Pharm. Sci., 1974, 63, 1896, (ms)
• IARC Monog., 1977, 13, 183; Suppl. 7, 316; Suppl. 6, 459, (rev, tox)
• Davies, D.S., J. Int. Med. Res., (Suppl. 2), 1977, 5, 15, (rev, metab)
• Singh, T.P. et al., J.C.S. Perkin 2, 1977, 693, (cryst struct)
• Aabakke, J., Clin. Pharmacokinet., 1978, 3, 369, (rev)
• Singh, S.P. et al., J. Het. Chem., 1978, 15, 13, (cmr)
• Ali, S.L. et al., Anal. Profiles Drug Subst., 1982, 11, 483, (rev)
• Tobin, T. et al., J. Vet. Pharmacol. Ther., 1986, 9, 1, (rev, pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5204
• Kaneniwa, N. et al., Chem. Pharm. Bull., 1988, 36, 1063; 1074, (polymorphism)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 29
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BRF500