Delafloxacin
Basic information
- CAS
189279-58-1- Standard SMILES
Nc1nc(-n2cc(C(=O)O)c(=O)c3cc(F)c(N4CC(O)C4)c(Cl)c32)c(F)cc1F- InChIKey
DYDCPNMLZGFQTM-UHFFFAOYSA-N- Molecular formula
- C18H12ClF3N4O4
- Average molar mass
- 440.8 g/mol
- Monoisotopic mass
- 440.0499171
Overview
Delafloxacin is a fluoroquinolone antibiotic which has been used in trials studying the treatment and basic science of Gonorrhea, Hepatic Impairment, Bacterial Skin Diseases, Skin Structure Infections, and Community Acquired Pneumonia, among others. It was approved in June 2017 under the trade name Baxdela for use in the treatment of acute bacterial skin and skin structure infections.
Names & identifiers
- Preferred name
- Delafloxacin
- IUPAC
- 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid
- English name
- ABT-492
- Molecular formula
- C18H12ClF3N4O4
- Molecular weight
- 440.76
Names & synonyms
Delafloxacin189279-58-11-(6-AMINO-3,5-DIFLUOROPYRIDIN-2-YL)-8-CHLORO-6-FLUORO-7-(3-HYDROXYAZETIDIN-1-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACIDWQ-3034RX-3341ABT492delafloxacinedelafloxacinoDelafloxacinum1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid3-Quinolinecarboxylic acid, 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-DTXSID40172331
Show more names
Delafloxacin ImpurityWQ3034CS-711CS-2335ABT492/ABT-492
6315412YVFWQ 3034J01MA23RefChem:57796DTXCID9094822ABT-492BaxdelaAbt 492
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 120 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 3
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 755
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
Pharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Fluoroquinolones; Quinolones
EMA approved medicines: Human medicine
Physicochemical properties
- Melting point
- 238 · 238-241℃
- Boiling point
- 698.5 · 698.5±55.0 °C(Predicted)
- Density
- 1.796 · 1.796
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Very Slightly, Heated, Sonicated)
- pka
- 5.49 · 5.49±0.50(Predicted)
- form
- powder
- color
- white to beige
- InChI
- InChI=1S/C18H12ClF3N4O4/c19-12-13-7(1-9(20)14(12)25-3-6(27)4-25)15(28)8(18(29)30)5-26(13)17-11(22)2-10(21)16(23)24-17/h1-2,5-6,27H,3-4H2,(H2,23,24)(H,29,30)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Hepatotoxicity
Delafloxacin, like other fluoroquinolones, is associated with a low rate (3% to 4%) of serum enzyme elevations during therapy. These abnormalities are generally mild, asymptomatic and transient, resolving even with continuation of therapy. ALT elevations above 5 times the upper limit of normal occur in 1% or less of subjects. Although delafloxacin may not have been clearly linked to cases of clinically apparent liver injury, the other fluoroquinolones, such as ciprofloxacin, levofloxacin and moxifloxacin, rank among the 25 most common causes of drug induced liver injury in many case series. Estimates of the frequency of liver injury from fluoroquinolones have been 1:15,000 to 1:25,000 exposed persons. Delafloxacin has been in clinical use for a short time only, but is likely to have a similar frequency and pattern of liver injury as the other fluoroquinolones.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingDelafloxacin is 84% bound to human plasma proteins. It primarily binds to serum albumin.
PharmacodynamicsDelafloxacin is a fluoroquinolone antibacterial drug which kills bacterial cells.
Mechanism of Action
Delafloxacin inhibits the activity of bacterial DNA topoisomerase IV and DNA gyrase (topoisomerase II). This interferes with bacterial DNA replication by preventing the relaxation of positive supercoils introduced as part of the elongation process. The resultant strain inhibits further elongation. Delafloxacin exerts concentration-dependent bacteriocidal activity.
Biological Half-LifeThe mean half life of elimination of Delafloxacin is 3.7 hours after a single intravenous administration. The mean half life of elimination for multple oral administrations is 4.2-8.5 hours.
Metabolism/MetabolitesDelafoxacin is primarily metabolized via glucuronidation mediated by UDP glucuronosyltransferase 1-1, UDP-glucuronosyltransferase 1-3, and UDP-glucuronosyltransferase 2B15. Less than 1% is metabolized via oxidation.
FDA Pharmacological Classification
6315412YVF
DELAFLOXACIN
Established Pharmacologic Class [EPC] - Fluoroquinolone Antibacterial
Chemical Structure [CS] - Fluoroquinolones
Delafloxacin is a Fluoroquinolone Antibacterial.
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Absorption, Distribution and Excretion
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Compound notes
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