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

• ChemBase编号: 691
• 分子式: C19H20N2O2
• 平均质量: 308.3743
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione
• IUPAC传统名: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione; phenylbutazone
• 商标名: '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
• 别名: 苯基丁氮酮; Phenylbutazone; 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

登记号

• CAS号: 50-33-9
• EC号: 200-029-0
• MDL号: MFCD00005500
• Beilstein号: 290080
• 默克索引号: 147277
• PubChem SID: 24277729; 160964154; 46507038
• PubChem CID: 4781
• CHEBI ID: 48574
• ATC码: M02AA01; M01AA01
• CHEMBL: 101
• Chemspider ID: 4617
• DrugBank ID: DB00812
• KEGG ID: D00510
• 美国药典/FDA物质标识码: GN5P7K3T8S
• 维基百科标题: Phenylbutazone

理论计算性质

JChem

• Acid pKa: 5.1349697
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.6229165
• LogD (pH = 7.4): 2.2602339
• Log P: 4.135798
• 摩尔折射率: 88.7583 cm^3
• 极化性: 34.466145 Å^3
• 极化表面积: 40.62 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.81
• LOG S: -3.33
• 溶解度: 1.44e-01 g/l

分子性质

理化性质

• 溶解度: 47.5 mg/L; Chloroform; Methanol
• 外观: Off-Whtie Solid
• 熔点: 102-105°C; 105 °C; 105-108°C; 106 - 108°C; 106-108 °C(lit.)
• 疏水性(logP): 3.385; 3.7

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: UQ8225000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811; UN2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 20/21/22-36/37/38; 22-36-40-63; R:22-36
• 安全公开号: 26-36/37; S:26-36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H312-H315-H319-H332-H335; H301-H319-H351-H361
• GHS警示性声明: P261-P280-P301 + P310-P305 + P351 + P338; P280H-P305+P351+P338-P309-P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 法定药品分级: rx-only
• 相关基因信息: human ... CYP2C9(1559), PTGIS(5740), PTGS2(5743)
• 生物活性机理: Prostaglandin antagonist

产品相关信息

• 纯度: ≥99.0%; 98%; null%
• 级别: SAJ special grade
• 成盐信息: Free Base
• 应用领域: Analgesic; Antiinflammatory, esp. antirheumatic; Antipyretic; Use limited due to toxicity
• Empirical Formula (Hill Notation): C19H20N2O2

详细说明

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.

参考文献

• http://en.wikipedia.org/wiki/Phenylbutazone
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• Mondelli, R. et al., Gazz. Chim. Ital., 1965, 95, 1371, (pmr)
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• IARC Monog., 1977, 13, 183; Suppl. 7, 316; Suppl. 6, 459, (rev, tox)
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• 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