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Details

Stereochemistry ACHIRAL
Molecular Formula C18H12ClF3N4O4
Molecular Weight 440.76
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DELAFLOXACIN

SMILES

NC1=NC(N2C=C(C(O)=O)C(=O)C3=C2C(Cl)=C(N4CC(O)C4)C(F)=C3)=C(F)C=C1F

InChI

InChIKey=DYDCPNMLZGFQTM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C18H12ClF3N4O4
Molecular Weight 440.76
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Comparative antimicrobial activities of the newly synthesized quinolone WQ-3034, levofloxacin, sparfloxacin, and ciprofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex.
2000 Feb
New antibiotics for antibiotic-resistant bacteria.
2009 May 28
Methicillin-resistant Staphylococcus aureus: a pervasive pathogen highlights the need for new antimicrobial development.
2010 Dec
Patents

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
Created
by admin
on Mon Oct 21 19:49:38 UTC 2019
Edited
by admin
on Mon Oct 21 19:49:38 UTC 2019
Record UNII
6315412YVF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DELAFLOXACIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
DELAFLOXACIN [INN]
Common Name English
RX-3341
Code English
ABT-492
Code English
WQ-3034
Code English
DELAFLOXACIN [WHO-DD]
Common Name English
3-QUINOLINECARBOXYLIC ACID, 1-(6-AMINO-3,5-DIFLUORO-2-PYRIDINYL)-8-CHLORO-6-FLUORO-1,4-DIHYDRO-7-(3-HYDROXY-1-AZETIDINYL)-4-OXO-
Common Name English
DELAFLOXACIN [USAN]
Common Name English
BAXDELA
Brand Name English
1-(6-AMINO-3,5-DIFLUOROPYRIDIN-2-YL)-8-CHLORO-6-FLUORO-7-(3-HYDROXYAZETIDIN-1-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000193223
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
WHO-ATC J01MA23
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
NCI_THESAURUS C795
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
Code System Code Type Description
INN
9064
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
PUBCHEM
487101
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
ChEMBL
CHEMBL2105637
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
RXCUI
1927663
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
CAS
189279-58-1
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
NCI_THESAURUS
C87390
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
EPA CompTox
189279-58-1
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
Following a single oral dose of 14C-labeled delafloxacin, 50% of the radioactivity is excreted in urine as unchanged delafloxacin and glucuronide metabolites and 48% is excreted in feces as unchanged delafloxacin.
FECAL; URINE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INDUCER
Delafloxacin was a mild inducer (less than 2 fold) of CYP3A4 at a clinically relevant concentration.
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
After single intravenous dose of 14C-labeled delafloxacin, 65% of the radioactivity is excreted in urine as unchanged delafloxacin and glucuronide metabolites and 28% is excreted in feces as unchanged delafloxacin.
FECAL; URINE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INDUCER
Delafloxacin was a mild inducer (less than 2 fold) of CYP2C9 at a concentration of 100 ?M
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC MULTIPLE ORAL ADMINISTRATION

Tmax PHARMACOKINETIC FASTED CONDITION

ORAL ADMINISTRATION

NOAEL TOXICITY ORGAN SYSTEM OR TYPE OF EFFECT
TOXICITY
SPECIES
TOXICITY
ROUTE OF ADMINISTRATION
TOXICITY
COMMENTS

Volume of Distribution PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

SINGLE DOSE