基本情報
- 標準SMILES
COc1c(N2CCNC(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12- InChIKey
XUBOMFCQGDBHNK-UHFFFAOYSA-N- 分子式
- C19H22FN3O4
- 平均分子量
- 375.4 g/mol
- 単同位体質量
- 375.1594344
概要
Gatifloxacin is a monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes. It has a role as an antimicrobial agent, an antiinfective agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a quinolone, a quinolinemonocarboxylic acid, an organofluorine compound, a N-arylpiperazine and a quinolone antibiotic.
名称と識別子
- 優先名称
- Gatifloxacin
- IUPAC
- 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
名称と別名
名称をさらに表示
データベース識別子
- CAS
112811-59-3- PubChem CID
- 5379
- DTXSID
DTXSID5045704- ChEMBL
CHEMBL31- ChEBI
CHEBI:5280- UNII
- 81485Y3A9A
- EC Number
- 664-293-2
- Nikkaji
- J523.172H
物性
構造計算による物性
- XLogP
- -0.7
- 極性表面積
- 82.1 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
- 4
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 653
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
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
182-185 °C
182 - 185 °C
Dissociation Constants
8.74
6
6
9.4
Collision Cross Section
189.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
189.03 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
安全と法規制
GHS分類
GHS Classification
Warning
H302 (97.5%): 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)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
毒性情報
Treatment
In the event of acute oral overdose, the stomach should be emptied by inducing vomiting or by gastric lavage. The patient should be carefully observed (including ECG monitoring) and given symptomatic and supportive treatment. Adequate hydration should be maintained. (L1712)
化学と産業
薬理情報
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QS - Sensory organs
QJ - Antiinfectives for systemic use
Pharmacodynamics
Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.
Metabolism/Metabolites
Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites
Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites Half Life: 7-14 hours
FDA Pharmacological Classification
81485Y3A9A
GATIFLOXACIN ANHYDROUS
Established Pharmacologic Class [EPC] - Quinolone Antimicrobial
Chemical Structure [CS] - Quinolones
Gatifloxacin anhydrous is a Quinolone Antimicrobial.
GATIFLOXACIN
MeSH Pharmacological Classification
Sterile solutions that are intended for instillation into the eye. It does not include solutions for cleaning eyeglasses or CONTACT LENS SOLUTIONS.
Substances that inhibit the growth or reproduction of BACTERIA.
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.
用途と製造
Uses
Use (kg) in USA (2002): 7250
For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes
関連反応
関連ノート
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