8-ヒドロキシ-5-ニトロキノリン
Nitroxoline
基本情報
- CAS
4008-48-4- 標準SMILES
O=[N+]([O-])c1ccc(O)c2ncccc12- InChIKey
RJIWZDNTCBHXAL-UHFFFAOYSA-N- 分子式
- C9H6N2O3
- 平均分子量
- 190.16 g/mol
- 単同位体質量
- 190.03784206
概要
Nitroxoline is a monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5. It has a role as an antimicrobial agent, an antiinfective agent, an antifungal agent and a renal agent. It is a C-nitro compound and a monohydroxyquinoline.
名称と識別子
- 優先名称
- Nitroxoline
- IUPAC
- 5-nitroquinolin-8-ol
- 現地名
- 8-ヒドロキシ-5-ニトロキノリン
- 英語名
- Nitroxoline
- 分子式
- C9H6N2O3
- 分子量
- 190.16
名称と別名
NITROXOLINE5-nitroquinolin-8-ol4008-48-48-Hydroxy-5-nitroquinoline5-Nitro-8-quinolinol5-Nitro-8-hydroxyquinoline5-NitroxNitroxolina5-NOKNitroxolinum5-Nitro-8-oxyquinoline5NOK
名称をさらに表示
8-ヒドロキシ-5-ニトロキノリンニビオール5-ニトロ-8-ヒドロキシキノリン5-ニトロキノリン-8-オールニトロキソリンウロコーリ5-ニトロ-8-キノリノールノキシビオールエンテロコールウリトロール8ヒドロキシ5ニトロキノリン8‐ヒドロキシ‐5‐ニトロキノリンNitroxolinNiroxolineA-82bas58Noxin
DTXSID4046284NiceneNSC-74947A8M33244M6DTXCID2026284CHEBI:67121RefChem:166162223-662-4
データベース識別子
- CAS
4008-48-4- PubChem CID
- 19910
- DTXSID
DTXSID4046284- ChEMBL
CHEMBL1454910- ChEBI
CHEBI:67121- UNII
- A8M33244M6
- EC Number
- 223-662-4
- Nikkaji
- J3.716H
物性
構造計算による物性
- XLogP
- 2.1
- 極性表面積
- 78.9 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 4
- 回転可能結合数
- 0
- 重原子数
- 14
- 形式電荷
- 0
- 複雑度
- 229
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals
SpringerMaterials PropertiesBoiling point
LogP1.99
Solubility
2.73e+00 g/L
>28.5 [ug/mL] (The mean of the results at pH 7.4)
Melting Point180 °C
Physical DescriptionSolid
物理化学的性質
- 融点
- 181 · 181-183 °C(lit.)
- 沸点
- 325.64 °C · 325.64°C (rough estimate)
- 比重(密度)
- 1.3907 · 1.3907 (rough estimate)
- 屈折率
- 1.557 · 1.5570 (estimate)
- 貯蔵温度
- Keep in dark place,Inert atmosphere,Room temperature
- 溶解性
- アルコール: 非常に溶けにくい
- 酸解離定数(Pka)
- 2.55 · 2.55±0.10(Predicted)
- 外見
- powder to crystal
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
Danger
H301 (87.3%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Other Safety InformationIMAP assessments - 8-Quinolinol, 5-nitro-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (87.3%)
安全データ
- wgk
- 3
- rtecs
- VC8225000
- ridadr
- UN 2811 6.1/PG 3
- 毒性
- LD50 oral in rat: 510mg/kg
- hs_code
- 29334900
- risk_code
- 23/24/25-36/37/38-22/24/25-20/21/22
- hazard_code
- T,Xi,Xn
- hazard_note
- Toxic/Irritant
- safety_code
- 26-36-45
- hazard_class
- 6.1
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- 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
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of ActionThis drug may also have antitumor activity by inhibition of type 2 methionine aminopeptidase (MetAP2) protein which is involved in angiogenesis. Its antibacterial activity may stem from the metal ion complexation vital for bacterial growth.
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Cellular LocationsCytoplasm
用途と製造
UsesUse (kg; approx.) in Germany (2009): >1000
応用分野
用途有機合成原料、抗菌剤原料。
説明Nitroxoline is an 8-hydroxyquinoline that has diverse biological activities, including antibacterial, antiproliferative, and bromodomain interaction-inhibiting properties. Nitroxoline is active against the bacteria E. coli, S. aureus, E. faecalis, K. pneumoniae, and P. mirabilis in vitro (MIC90s = 4, 4, 8, 8, and 8 mg/L, respectively). It also inhibits biofilm formation of certain strains of multidrug-resistant (MDR) A. baumannii and P. aeruginosa, as well as methicillin-resistant S. aureus (MRSA) and S. epidermidis (MRSE) with minimum biofilm eradication concentration (MBEC) values of 46.9, 1,500, 188, and 125 μM, respectively. Nitroxoline inhibits the growth of human U87 and U251 glioma, A549 lung, and PC3 prostate cancer cells (IC50s = 50, 6, 38, and 23 μg/ml, respectively). In vivo, it reduces tumor growth in a PTEN- and KRAS-driven glioma mouse model when administered at a dose of 80 mg/kg per day. Nitroxoline also inhibits the interaction between the first bromodomain of bromodomain-containing protein 4 (BRD4) with acetylated histone H4 with an IC50 value of 0.98 μM.
関連反応
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化合物ノート
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