기본 정보
- CAS
4008-48-4- 표준 SMILES
O=[N+]([O-])c1ccc(O)c2ncccc12- InChIKey
RJIWZDNTCBHXAL-UHFFFAOYSA-N- 분자식
- C9H6N2O3
- 평균 분자량
- 190.16 g/mol
- 단동위원소 질량
- 190.03784206
이름 및 식별자
- 우선 이름
- Nitroxoline
- IUPAC
- 5-nitroquinolin-8-ol
- 현지명
- 8-히드록시-5-니트로퀴노린
- 영어명
- Nitroxoline
- 분자식
- C9H6N2O3
- 분자량
- 190.16
이름 및 동의어
NITROXOLINE5-nitroquinolin-8-ol4008-48-48-Hydroxy-5-nitroquinoline5-Nitro-8-quinolinol5-Nitro-8-hydroxyquinoline5-Nitrox5-NOK5-Nitro-8-oxyquinolineNitroxolina5NOKNitroxolinum
이름 더 보기
8-히드록시-5-니트로퀴노린나이트록솔린나이트록솔린및그염류NitroxolinNiroxolineA-82bas58Noxin
DTXSID4046284NSC-74947A8M33244M6DTXCID2026284CHEBI:67121NiceneRefChem:166162223-662-4
데이터베이스 식별자
- CAS
4008-48-4- PubChem CID
- 19910
- DTXSID
DTXSID4046284- ChEMBL
CHEMBL1454910- ChEBI
CHEBI:67121- UNII
- A8M33244M6
- EC Number
- 223-662-4
- Nikkaji
- J3.716H
물성
구조 계산 물성
- XLogP
- 2.1
- 극성 표면적
- 78.9 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 14
- 형식 전하
- 0
- 복잡도
- 229
실험 및 물리화학적 성질
LogP
1.99
1.99
Solubility
2.73e+00 g/L
>28.5 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
180
180 °C
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 181 · 181-183 °C(lit.)
- 끓는 점
- 325.64 °C · 325.64°C (rough estimate)
- 밀도
- 1.3907 · 1.3907 (rough estimate)
- 굴절률
- 1.557 · 1.5570 (estimate)
- 저장 조건
- Keep in dark place,Inert atmosphere,Room temperature
- 용해도
- 알코올: 매우 약간 용해됨
- 산도 계수 (pKa)
- 2.55 · 2.55±0.10(Predicted)
- 물리적 상태
- powder to crystal
- 색상
- Light yellow to Brown to Dark green
- Merck
- 14 · 14,6655
- Henry's Law Constant
안전 및 규제
GHS 분류
GHS Classification
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.
유해성 정보
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%)
안전 데이터
- wgk
- 3
- rtecs
- VC8225000
- ridadr
- UN 2811 6.1/PG 3
- 독성
- LD50 oral in rat: 510mg/kg
화학 및 산업
약리 정보
ATC Code
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
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
용도 및 제조
Uses
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
응용 분야
개요Nitroxoline 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.
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