Delafloxacin

Delafloxacin
Clinical data

ATC code	none
Legal status
Legal status	Investigational
Identifiers
IUPAC name 1-(6-amino-3,5-difluoro-2-pyridyl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-quinoline-3-carboxylic acid
CAS Number	189279-58-1
PubChem (CID)	487101
ChemSpider	427049
UNII	6315412YVF^Y
KEGG	D09330
ChEMBL	CHEMBL2105637
Chemical and physical data
Formula	C₁₈H₁₂ClF₃N₄O₄
Molar mass	440.76 g/mol
3D model (Jmol)	Interactive image
SMILES Fc4cc(F)c(nc4N1\C=C(\C(=O)O)C(=O)c2c1c(Cl)c(c(F)c2)N3CC(O)C3)N

Delafloxacin (developmental code name RX-3341) is a fluoroquinolone antibiotic being developed by Rib-X Pharmaceuticals, Inc.

It is more active (lower MIC90) than other quinolones against Gram-positive bacteria such as MRSA. In contrast to most approved fluoroquinolones, which are zwitterionic, delafloxacin has an anionic character, which results in a 10-fold increase in delafloxacin accumulation in both bacteria and cells at acidic pH. This property is believed to confer to delafloxacin an advantage for the eradication of Staphylococcus aureus in acidic environments, including intracellular infections.^[1]

Clinical trials

Phase II clinical trials have been completed,^[2]^[3]^[4] including a trial with tigecycline as a comparator^[5] The company states delafloxacin met its primary and secondary efficacy endpoints based on the draft guidance from the FDA.

A Phase III trial for acute bacterial skin and skin structure infections (ABSSSI) is due to begin in the 2nd half of 2012.^[6]

References

↑ Lemaire, S. et al. Contrasting Effects of Acidic pH on the Extracellular and Intracellular Activities of the Anti-Gram-Positive Fluoroquinolones Moxifloxacin and Delafloxacin against Staphylococcus aureus Antimicrob. Agents Chemother. February 2011; 55:649-658 doi:10.1128/AAC.01201-10
↑ http://www.bio-medicine.org/biology-technology-1/Rib-X-Pharmaceuticals-Announces-Positive-Phase-2-Study-Results-for-Delafloxacin-and-a--2425-Million-Financing-10093-1/
↑ http://clinicaltrials.gov/ct2/show/NCT00719810
↑ http://www.medicalnewstoday.com/articles/132200.php "Rib-X Pharmaceuticals Reports Positive Top-Line Results From Phase 2 Study Of Delafloxacin" 9 Dec 2008
↑ http://www.citybizlist.com/lstg/lstgDetail.aspx?id=45749 "ABS Ventures Joins $25M Series D Rib-X Pharmaceuticals Inc." 5 Feb 2009
↑ Delafloxacin - Pipeline - Rib-X Pharmaceuticals. Accessed: 6/27/2012.

Antibacterials: nucleic acid inhibitors (J01E, J01M)

Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Trimethoprim^#
- Brodimoprim
- Tetroxoprim
- Iclaprim^†

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin Rifalazil^§

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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