U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H12ClF3N4O4.C7H17NO5
Molecular Weight 635.974
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DELAFLOXACIN MEGLUMINE

SMILES

CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.NC1=C(F)C=C(F)C(=N1)N2C=C(C(O)=O)C(=O)C3=CC(F)=C(N4CC(O)C4)C(Cl)=C23

InChI

InChIKey=AHJGUEMIZPMAMR-WZTVWXICSA-N
InChI=1S/C18H12ClF3N4O4.C7H17NO5/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;1-8-2-4(10)6(12)7(13)5(11)3-9/h1-2,5-6,27H,3-4H2,(H2,23,24)(H,29,30);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1

HIDE SMILES / InChI

Molecular Formula C7H17NO5
Molecular Weight 195.2136
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C18H12ClF3N4O4
Molecular Weight 440.76
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Delafloxacin (CAS registry number 189279-58-1) was described as WQ-3034 by Wakunaga Pharmaceutical Co., Ltd., Osaka & Hiroshima, Japan. It was first licensed in 1999 to Abbott Park, IL, and further developed as ABT-492. Delafloxacin (Baxdela), a fluoroquinolone antibiotic, is currently being developed by Melinta Therapeutics. It is a novel investigational fluoroquinolone in development for the treatment of uncomplicated gonorrhea, and acute bacterial skin and skin structure infections. Delafloxacin shows MICs remarkably low against Gram-positive organisms and anaerobes and similar to those of ciprofloxacin against Gram-negative bacteria. It remains active against most fluoroquinolone-resistant strains, except enterococci. Its potency is further increased in acidic environments (found in many infection sites). Delafloxacin is active on staphylococci growing intracellularly or in biofilms. Delafloxacin is a dual-targeting fluoroquinolone, capable of forming cleavable complexes with DNA and topoisomerase IV or DNA gyrase and of inhibiting the activity of these enzymes in both Gram-positive and Gram-negative bacteria. On Oct 24, 2016, Melinta Therapeutics Submitted Baxdela New Drug Application for hospital-treated skin infections.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BAXDELA
Curative
BAXDELA
Curative
BAXDELA

Cmax

ValueDoseCo-administeredAnalytePopulation
8.94 μg/mL
300 mg single, intravenous
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens
7.17 μg/mL
450 mg single, oral
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens
9.29 μg/mL
300 mg 2 times / day steady-state, intravenous
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens
7.45 μg/mL
450 mg 2 times / day steady-state, oral
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
21.8 μg × h/mL
300 mg single, intravenous
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens
22.7 μg × h/mL
450 mg single, oral
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens
23.4 μg × h/mL
300 mg 2 times / day steady-state, intravenous
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens
30.8 μg × h/mL
450 mg 2 times / day steady-state, oral
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.7 h
300 mg single, intravenous
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
16%
300 mg single, intravenous
DELAFLOXACIN MEGLUMINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
900mg orally (2 x 450 mg tablets) administered once
Route of Administration: Oral
In Vitro Use Guide
Delafloxacin demonstrated potent in vitro activity against this set of Staphylococcus aureus (MRSA) isolates, with MICs of 0.008-1 mg/L and an MIC(50) and MIC(90) of 0.03 and 0.5 mg/L, respectively.
Substance Class Chemical
Record UNII
N7V53U4U4T
Record Status Validated (UNII)
Record Version