基本情報
- CAS
31430-15-6- 標準SMILES
COC(=O)Nc1nc2ccc(C(=O)c3ccc(F)cc3)cc2[nH]1- InChIKey
CPEUVMUXAHMANV-UHFFFAOYSA-N- 分子式
- C16H12FN3O3
- 平均分子量
- 313.28 g/mol
- 単同位体質量
- 313.08626942
概要
Flubendazole is a member of the class of mebendazole in which the benzoyl group is replaced by a p-fluorobenzoyl group. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections. It has a role as an antinematodal drug and a teratogenic agent. It is a member of benzimidazoles, a carbamate ester, an organofluorine compound and an aromatic ketone.
名称と識別子
- 優先名称
- Flubendazole
- IUPAC
- methyl N-[6-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate
- 現地名
- フルベンダゾール
- 英語名
- Flubendazole
- 分子式
- C16H12FN3O3
- 分子量
- 313.28
名称と別名
Flubendazole31430-15-6FlubendazolFlubendazolumR 17,889Methyl 5-(p-fluorobenzoyl)-2-benzimidazolecarbamateDTXSID8023058R 17899NSC-313680(5-(4-Fluorobenzoyl)-1H-benzimidazole-2-yl)carbamic acid methyl esterR8M46911LRCarbamic acid, (5-(4-fluorobenzoyl)-1H-benzimidazol-2-yl)-, methyl ester
名称をさらに表示
フルベルマールフルベンダゾールフルモキサールフルベノール5-(p-フルオロベンゾイル)-1H-ベンゾイミダゾール-2-カルバミン酸メチル[5-(4-フルオロベンゾイル)-1H-ベンゾイミダゾール-2-イル]カルバミド酸メチルフルベンダゾール標準品[5-(4-フルオロベンゾイル)ベンゾイミダゾール-2-イル]カルバミン酸メチルN-(5-(4-フルオロベンゾイル)-1H-ベンゾイミダゾール-2-イル)カルバミド酸メチル2-(メトキシカルボニルアミノ)-5-(4-フルオロベンゾイル)-1H-ベンゾイミダゾールメチル N-[5-(4-フルオロベンゾイル)-1H-1,3-ベンゾジアゾール-2-イル]カルバマートFlubendazole Polymorph BR-17899R 17889FLUMOXALFLUBENOLFLUVERNALFLUMOXANEfluvermalFlubenvet
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 84.1 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 4
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 454
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antiparasitic products, insecticides and repellents -> Antiprotozoals
Animal Drugs
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point> 260
Collision Cross Section177.36 Ų [M-H]-
物理化学的性質
- 融点
- 290 °C · 290°C
- 比重(密度)
- 1.372 · 1.3720 (estimate)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 水、アルコール、塩化メチレンにほとんど溶けない
- 酸解離定数(Pka)
- 10.66 · 10.66±0.10(Predicted)
- 外見
- Solid
- 色
- ホワイトからオフホワイト
- Merck
- 14 · 14,4118
- 主な用途
- 法医学と毒物学医薬品（低分子化合物）
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 23.8% (5 of 21) of reports.
Warning
H361 (66.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 21 reports by companies from 7 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory InformationFlubendazole: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Carbamic acid, [5-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]-,methyl ester: Environment tier I assessment
Hazard Classes and CategoriesRepr. 2 (66.7%)
安全データ
- wgk
- 2
- rtecs
- DD6497500
- 毒性
- LD50 in mice, rats, guinea pigs (mg/kg): >2560 orally (Thienpont)
- hs_code
- 29339900
- risk_code
- 22
- safety_code
- 44
- ストレージクラス
- 10 - Combustible liquids
化学と産業
薬理情報
ATC Code
P - Antiparasitic products, insecticides and repellents
QP - Antiparasitic products, insecticides and repellents
Mechanism of Action
Flubendazole is a benzimidazole that inhibits microtubule function by binding tubulin and inhibiting tubulin polymerization. It binds to the colchicine-binding site of the tubulin protein, located at the interface of the alpha (α) and beta (β) tubulin heterodimer.
MeSH Pharmacological ClassificationSubstances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
用途と製造
Use Classification
Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
応用分野
説明Flubendazole is a benzimidazole carbamate anthelmintic. It completely eliminates larvae in a mouse model of A. cantonensis infection and exhibits a mean larval reduction of 100% in a T. spiralis infection model when administered at doses of 5 and 50 mg/kg per day, respectively. Flubendazole inhibits mammalian tubulin polymerization (IC50 = 2.5 μM) and inhibits binding of [3H]mebendazole to H. contortus L3 larval tubulin (IC50 = 0.17 μM). Flubendazole also inhibits the proliferation of BT-549, SK-BR-3, MDA-MB-231, and MCF-7 breast cancer cells (IC50s = 0.72, 1.51, 1.75, and 5.51 μM, respectively) and reduces tumor growth in an MDA-MB-231 mouse xenograft model when administered at a dose of 25 mg/kg.
使用An anthelmintic.
一般的な説明Flubendazol is a broad spectrum anthelmintic, which belongs to the class of compounds known as benzimidazoles. It can be widely used in veterinary and human medicine. It mainly finds applications in deworming poultry, swine, dogs and cats.
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