基本情報
- CAS
98079-51-7- 標準SMILES
CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNC(C)C3)c(F)c21- InChIKey
ZEKZLJVOYLTDKK-UHFFFAOYSA-N- 分子式
- C17H19F2N3O3
- 平均分子量
- 351.35 g/mol
- 単同位体質量
- 351.13944791
概要
Lomefloxacin is a fluoroquinolone antibiotic, used (generally as the hydrochloride salt) to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery. It has a role as an antitubercular agent, an antimicrobial agent and a photosensitizing agent. It is a quinolone, a quinolinemonocarboxylic acid, a N-arylpiperazine, a quinolone antibiotic and a fluoroquinolone antibiotic.
名称と識別子
- 優先名称
- Lomefloxacin
- IUPAC
- 1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
- 現地名
- ロメフロキサシン
- 英語名
- Lomefloxacin
- 分子式
- C17H19F2N3O3
- 分子量
- 351.35
名称と別名
lomefloxacin98079-51-7LomefloxacineLomefloxacinoLomefloxacinumLFLX1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidSC-47111AL6BR2WJD8V1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid1,4-Dihydro-6,8-difluoro-1-ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidDTXSID4040680
名称をさらに表示
1-エチル-4-オキソ-6,8-ジフルオロ-7-(3-メチル-1-ピペラジニル)-1,4-ジヒドロキノリン-3-カルボン酸1-エチル-6,8-ジフルオロ-7-(3-メチルピペラジノ)-4-オキソ-1,4-ジヒドロ-3-キノリンカルボン酸1-エチル-6,8-ジフルオロ-1,4-ジヒドロ-7-(3-メチル-1-ピペラジニル)-4-オキソ-3-キノリンカルボン酸1-エチル-6,8-ジフルオロ-1,4-ジヒドロ-7-(3-メチル-1-ピペラジニル)-4-オキソキノリン-3-カルボン酸ロメフロキサシン1-エチル-6,8-ジフルオロ-1,4-ジヒドロ-4-オキソ-7-(3-メチル-1-ピペラジニル)キノリン-3-カルボン酸1-エチル-6,8-ジフルオロ-7-(3-メチルピペラジン-1-イル)-4-オキソ-1,4-ジヒドロキノリン-3-カルボン酸1-エチル-6,8-ジフルオロ-1,4-ジヒドロ-4-オキソ-7-(3-メチルピペラジノ)-3-キノリンカルボン酸1,4-ジヒドロ-4-オキソ-1-エチル-6,8-ジフルオロ-7-(3-メチルピペラジン-1-イル)キノリン-3-カルボン酸dm-10
物性
構造計算による物性
- XLogP
- -0.8
- 極性表面積
- 72.9 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 8
- 回転可能結合数
- 3
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 585
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
LogP2.8
Solubility1.06e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones
Melting Point
239-240.5 °C
239 - 240.5 °C
Physical DescriptionSolid
Dissociation Constants5.742
Collision Cross Section
191.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
191.04 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 239 · 239-240 C
- 沸点
- 542.7 · 542.7±50.0 °C(Predicted)
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
危険有害性情報
Regulatory InformationStatus: Active Update: 17-03-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19305
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
lomefloxacin
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- wgk
- 3
- rtecs
- VB1997500
- 毒性
- LD50 in mice (mg/kg): 245.6 i.v.; >4000 orally (Itoh)
- hs_code
- 29419000
- risk_code
- 22-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 26-36
化学と産業
薬理情報
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QS - Sensory organs
Protein Binding10%
Pharmacodynamics
Lomefloxacin is a fluoroquinolone antibiotic used to treat chronic bronchitis, as well as complicated and uncomplicated urinary tract infections. It is also used as a prophylactic or preventative treatment to prevent urinary tract infections in patients undergoing transrectal or transurethral surgical procedures. Flouroquinolones such as lomefloxacin possess excellent activity against gram-negative aerobic bacteria such as <i>E.coli</i> and <i>Neisseria gonorrhoea</i> as well as gram-positive bacteria including <i>S. pneumoniae</i> and <i>Staphylococcus aureus</i>. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.
Mechanism of Action
Lomefloxacin is a bactericidal fluoroquinolone agent with activity against a wide range of gram-negative and gram-positive organisms. The bactericidal action of lomefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.
Biological Half-Life8 hours
Metabolism/MetabolitesMinimally metabolized although 5 metabolites have been identified in human urine. 65% appears as the parent drug in urine and 9% as the glucuronide metabolite.
MeSH Pharmacological Classification
関連反応
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化合物ノート
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