CAS 4008-48-4 Nitroxoline (HCID 19910)

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-Nitrox5-NOK5-Nitro-8-oxyquinolineNitroxolina5NOKNitroxolinum

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

DTXSID4046284NSC-74947A8M33244M6DTXCID2026284CHEBI:67121NiceneRefChem: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 Å²
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

LogP · 2 件

1.99

Solubility · 2 件

2.73e+00 g/L

>28.5 [ug/mL] (The mean of the results at pH 7.4)

Melting Point · 2 件

180

180 °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
色: Light yellow to Brown to Dark green
Merck: 14 · 14,6655
Henry's Law Constant: 2.7 · 2.7×103 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
InChI: InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
InChIKey: RJIWZDNTCBHXAL-UHFFFAOYSA-N
SMILES: N1C2C(=C([N+]([O-])=O)C=CC=2O)C=CC=1
NISTの化学物質情報: 8 · 8-Hydroxy-5-nitroquinoline(4008-48-4)

化学的性質

化学的特性ochre-yellow to brownish crystalline powder

安全と法規制

GHS分類

GHS Classification · 5 件

Danger

H301 (87.3%): Toxic if swallowed [Danger Acute toxicity, oral]；H302 (12.7%): Harmful if swallowed [Warning Acute toxicity, oral]；H311 (87.3%): Toxic in contact with skin [Danger Acute toxicity, dermal]；H315 (98.2%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (98.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H331 (87.3%): Toxic if inhaled [Danger Acute toxicity, inhalation]；H335 (96.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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.；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

Other Safety InformationIMAP assessments - 8-Quinolinol, 5-nitro-: Human health tier I assessment；IMAP assessments - 8-Quinolinol, 5-nitro-: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 3 (87.3%)；Acute Tox. 4 (12.7%)；Acute Tox. 3 (87.3%)；Skin Irrit. 2 (98.2%)；Eye Irrit. 2 (98.2%)；Acute Tox. 3 (87.3%)；STOT SE 3 (96.4%)

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 · 2 件

J - Antiinfectives for systemic use；J01 - Antibacterials for systemic use；J01X - Other antibacterials；J01XX - Other antibacterials；J01XX07 - Nitroxoline

QJ - Antiinfectives for systemic use；QJ01 - Antibacterials for systemic use；QJ01X - Other antibacterials；QJ01XX - Other antibacterials；QJ01XX07 - Nitroxoline

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 · 2 件

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

Uses · 1 件

Use (kg; approx.) in Germany (2009): >1000；Use (kg; exact) in Germany (2009): 1197；Consumption (g per capita; approx.) in Germany (2009): 0.0122；Consumption (g per capita; exact) in Germany (2009): 0.0146；Excretion rate: 1；Calculated removal (%): 22.9

応用分野 · 3 件

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.

使用antibacterial

上流・下流製品情報

上流原料

下流製品

5-アミノキノリン-8-オール 5-アミノ-8-ヒドロキシキノリン二塩酸塩 8-Quinolinol, 7-bromo-5-nitro-

サプライヤー100 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]

科瑞迪化学400-821-5857 021-64326257 · [email protected]

補足説明

定義ChEBI: A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.

化合物ノート

読み込み中…

8-ヒドロキシ-5-ニトロキノリン

基本情報