Fenbufen (HCID 3335)

概要

Fenbufen is a member of biphenyls and a 4-oxo monocarboxylic acid. It has a role as a non-steroidal anti-inflammatory drug.

名称と識別子

優先名称: Fenbufen
IUPAC: 4-oxo-4-(4-phenylphenyl)butanoic acid
現地名: フェンブフェン
英語名: Fenbufen
分子式: C16H14O3
分子量: 254.29

名称と別名

fenbufen36330-85-54-(4-Biphenylyl)-4-oxobutyric acid3-(4-Biphenylylcarbonyl)propionic acid3-(4-Phenylbenzoyl)propionic acidFenbufene4-(biphenyl-4-yl)-4-oxobutanoic acidFenbufenumgamma-Oxo(1,1'-biphenyl)-4-butanoic acidCL-822043-(4-Biphenylcarbonyl)propionic acidDTXSID9023043

名称をさらに表示

4-オキソ-4-(4-ビフェニリル)ブタン酸ブフェミドγ-オキソビフェニル-4-酪酸フェンブフェンγ-オキソ[1,1'-ビフェニル]-4-酪酸γ-オキソ-[1,1'-ビフェニル]-4-ブタン酸γ-オキソ[1,1'-ビフェニル]-4-ブタン酸4-(4-ビフェニリル)-4-オキソ酪酸3-(4-ビフェニリルカルボニル)プロピオン酸レデルフェンシノパールγ‐オキソ‐［1，1′‐ビフェニル］‐4‐ブタン酸4-(4-ビフェニル)-4-オキソ酪酸3-(4-フェニルベンゾイル)プロピオン酸フェンブフェン (JP17)γ-オキソ[1,1′-ビフェニル]-4-ブタン酸γ-オキソ-[1,1′-ビフェニル]-4-ブタン酸γ-オキソ[1,1′-ビフェニル]-4-酪酸4-{[1,1'-ビフェニル]-4-イル}-4-オキソブタン酸4-([1,1'-Biphenyl]-4-yl)-4-oxobutanoic acidbufemidcl82204napanolcinopalCinopolenbufenlederfenFenbufen CRS

NSC-757812CL 82,2049815R1WR9B(1,1'-BIPHENYL)-4-BUTANOIC ACID, gamma-OXO-DTXCID703043CHEBI:315994-[1,1'-biphenyl-4-yl]-4-oxobutanoic acid4-(1,1'-biphenyl-4-yl)-4-oxobutanoic acid

データベース識別子

CAS: 36330-85-5
PubChem CID: 3335
DTXSID: DTXSID9023043
ChEMBL: CHEMBL277522
ChEBI: CHEBI:31599
UNII: 9815R1WR9B
EC Number: 252-979-0
Nikkaji: J3.182H

物性

構造計算による物性

XLogP: 3.2
極性表面積: 54.4 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 5
重原子数: 19
形式電荷: 0
複雑度: 310

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

LogP2.91

Human DrugsPharmaceuticals

Melting Point185-187

Collision Cross Section150.36 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 184 · 184-187 °C (lit.)
沸点: 357.5 °C · 357.5°C (rough estimate)
比重(密度): 1.1565 · 1.1565 (rough estimate)
屈折率: 1.56 · 1.5600 (estimate)
貯蔵温度: 2 · 2-8°C
溶解性: 水に非常に溶けにくく、アセトン、エタノール (96%)、およびジクロロメタンに溶けにくい。
外見: Solid
酸解離定数(Pka): 4.3 · pKa 4.3(H2O tundened Iundened) (Uncertain)
色: White to off-white
水溶解度: 2.212 mg/L · 2.212mg/L(25℃)
Merck: 13 · 13,3990
主な用途: 法医学と毒物学医薬品（低分子化合物）獣医
InChI: 1S/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19)
InChIKey: ZPAKPRAICRBAOD-UHFFFAOYSA-N
SMILES: OC(=O)CCC(=O)c1ccc(cc1)-c2ccccc2
EPAの化学物質情報: 1 · [1,1'-Biphenyl]-4-butanoic acid, .gamma.-oxo- (36330-85-5)

化学的性質

化学的特性White Solid

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Other Safety InformationIMAP assessments - [1,1'-Biphenyl]-4-butanoic acid, .gamma.-oxo-: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全データ

wgk: 3
rtecs: DV1761000
ridadr: UN 2811 6.1/PG 3
毒性: LD50 in various strains of mice, rats (mg/kg): 795-1673, 200-720 orally; 506-811, 265-575 i.p. (Bolte)
hs_code: 2918300090
risk_code: 25
hazard_code: T
safety_code: 28-45
hazard_class: 6.1
packing_group: III
Hazard Classifications: Acute Tox. 3 Oral
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

ATC Code · 2 件

M - Musculo-skeletal system

QM - Musculo-skeletal system

MeSH Pharmacological Classification · 2 件

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.

用途と製造

Use ClassificationPharmaceuticals

応用分野 · 4 件

用途有機合成原料、薬理・生理作用研究用。

説明Fenbufen has been found to be an effective, well-tolerated drug for the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. Fenbufen is prepared by the Friedel-Crafts (aluminum chloride – nitrobenzene) acylation of biphenyl with succinic anhydride. The compound is metabolized in humans first to 4-hydroxy-4-biphenylbutyric acid (tmax 2.5 h) then to 4-biphenyl acetic acid (tmax 7.5 h). Both metabolites are more active than fenbufen itself and circulate for several hours (t1/2 10 h). This slow conversion of fenbufen to active metabolites having relatively long plasma half-lives allows for once a day dosing with this agent.

使用Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory

一般的な説明Fenbufen belongs to the class of non-steroidal anti-inflammatory drugs, widely used as an antipyretic and analgesic in medical applications. Its mode of action involves the inhibition of cyclooxygenase enzyme and thereby prevents the synthesis of certain prostaglandins.

上流・下流製品情報

上流原料

ビフェニルこはく酸無水物塩化アルミニウム(III)4-(4-Biphenylyl)butanoic acid methyl ester 4-シクロヘキシル-α-オキソベンゼンブタン酸 Fenbufen Methyl Ester 4-(4-ビフェニル)-4-オキソ酪酸エチル 3-(4-クロロベンゾイル)プロピオン酸 3-(4-ブロモベンゾイル)プロピオン酸テトラフェニルほう酸ナトリウム 4-フェニルベンゾイルクロリドフェニルボロン酸

下流製品

4-フェニルベンゼンブタン酸

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フェンブフェン

基本情報

概要