基本情報
- 標準SMILES
CCCCOc1ccc(CC(=O)NO)cc1- InChIKey
MXJWRABVEGLYDG-UHFFFAOYSA-N- 分子式
- C12H17NO3
- 平均分子量
- 223.27 g/mol
- 単同位体質量
- 223.1208434
名称と識別子
- 優先名称
- Bufexamac
- IUPAC
- 2-(4-butoxyphenyl)-N-hydroxyacetamide
- 現地名
- 4-ブトキシベンゼンアセトヒドロキサム酸
- 英語名
- Bufexamac
- 分子式
- C12H17NO3
- 分子量
- 223.27
名称と別名
名称をさらに表示
データベース識別子
- CAS
2438-72-4- PubChem CID
- 2466
- DTXSID
DTXSID7045368- ChEMBL
CHEMBL94394- ChEBI
CHEBI:31317- UNII
- 4T3C38J78L
- EC Number
- 219-451-1
- Nikkaji
- J3.390A
物性
構造計算による物性
- XLogP
- 1.9
- 極性表面積
- 58.6 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 6
- 重原子数
- 16
- 形式電荷
- 0
- 複雑度
- 200
実験および物理化学的性質
Solubility
Immiscible
>33.5 [ug/mL] (The mean of the results at pH 7.4)
Collision Cross Section
161.48 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];158.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
161 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 153 · 153-155°
- 沸点
- 364.56 °C · 364.56°C (rough estimate)
- 比重(密度)
- 1.1223 · 1.1223 (rough estimate)
- 屈折率
- 1.53 · 1.5300 (estimate)
- 貯蔵温度
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- 水にほとんど溶けず、ジメチルホルムアミドに溶け、酢酸エチル、メタノールに溶けにくい。
- 酸解離定数(Pka)
- 9.24 · 9.24±0.20(Predicted)
- 外見
- Solid
- 色
- ホワイトからオフホワイト
- Merck
- 14 · 14,1474
- CAS データベース
- 2438 · 2438-72-4(CAS DataBase Reference)
化学的性質
化学的特性White Solid
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral];H317 (33.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.;There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
安全データ
- wgk
- 2
- rtecs
- AK8280000
- 毒性
- LD50 orally in mice, rats: >8, >4 g/kg (Lambelin)
- hs_code
- 2928.00.2500
化学と産業
薬理情報
ATC Code
M - Musculo-skeletal system;M02 - Topical products for joint and muscular pain;M02A - Topical products for joint and muscular pain;M02AA - Antiinflammatory preparations, non-steroids for topical use;M02AA09 - Bufexamac
M - Musculo-skeletal system;M01 - Antiinflammatory and antirheumatic products;M01A - Antiinflammatory and antirheumatic products, non-steroids;M01AB - Acetic acid derivatives and related substances;M01AB17 - Bufexamac
QM - Musculo-skeletal system;QM02 - Topical products for joint and muscular pain;QM02A - Topical products for joint and muscular pain;QM02AA - Antiinflammatory preparations, non-steroids for topical use;QM02AA09 - Bufexamac
QM - Musculo-skeletal system;QM01 - Antiinflammatory and antirheumatic products;QM01A - Antiinflammatory and antirheumatic products, non-steroids;QM01AB - Acetic acid derivatives and related substances;QM01AB17 - Bufexamac
Pharmacodynamics
Bufexamac is a topically-active anti-inflammatory agent that inhibits the cyclooxygenase enzyme. In cutaneous and deep experimental inflammation, topical administration of bufexamac exerted a dose-related anti-inflammatory effect. In guinea pigs, bufexamax was shown to be more active than topical acetylsalicylic acid 5% or phenylbutazone 5% in delaying the local increase in temperature resulting from UV exposure. Bufexamac is unlikely to have any effect on wound healing.
Mechanism of Action
The full mechanism of action is unclear. It is proposed that bufexamac acts similarly to other non-steroidal anti-inflammatory drugs to inhibit prostaglandin biosynthesis _in vitro_, via inhibiting cyclo-oxygenase (COX) enzymes. Systematically administered bufexamac may accumulate preferentially in the adrenal cortex of rats and may play a role in adrenal stimulation; however its topical anti-inflammatory action is likely to be independent of this effect.
MeSH Pharmacological Classification
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.
Absorption, Distribution and Excretion
Method of application affects the extent of cutaneous absorption. Following rectal administration as suppositories, the systemic absorption was reported to be low.
Following topical administration of 5% bufexamac, the recovery in the urine was 3.5% of the applied dose within 144 hours. Studies in healthy volunteers receiving an oral dose of 125 to 500 mg indicate that an average of 80% of the total dose is excreted in the urine within 48 hours.
No data available.
No data available.
用途と製造
応用分野
使用Bufexamac is a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10). Bufexamac is a non-steroidal anti-inflammatory drug used topically as well as rectally. Formulations containing Bufexamac is used by many patients with eczematous disorders as an alternative to topical corticosteroids.
上流・下流製品情報
上流原料
サプライヤー50 社
補足説明
定義ChEBI: A hydroxamic acid derived from phenylacetamide in which the benzene moiety is substituted at C-4 by a butoxy group. It has anti-inflammatory, analgesic, and antipyretic properties.
関連反応
関連ノート
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