NAV

Delafloxacin

Identification

Summary

Delafloxacin is a fluoroquinolone antibiotic used to treat skin and skin structure infections.

Brand Names
Baxdela
Generic Name
Delafloxacin
DrugBank Accession Number
DB11943
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
3D
Similar Structures
Weight
Average: 440.76
Monoisotopic: 440.0499171
Chemical Formula
C18H12ClF3N4O4
Synonyms
  • Delafloxacin
External IDs
  • ABT-492
  • RX-3341
  • WQ-3034
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Pharmacology

Indication

Delafloxacin is indicated for the treatment of acute bacterial skin and skin structure infections caused by the Gram-positive organisms Staphylococcus aureus (including methicillin-resistant and methicillin-susceptible isolates), Staphylococcus haemolyticus, Staphylococcus lugdunensis, Streptococcus agalactiae, Streptococcus anginosus Group (including Streptococcus anginosus, Streptococcus intermedius, and Streptococcus constellatus), Streptococcus pyogenes, and Enterococcus faecalis as well as the Gram-negative organisms Escherichia coli, Enterobacter cloacae, Klebsiella pneumoniae, and Pseudomonas aeruginosa Label.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute bacterial skin and skin structure infection (absssi)•••••••••••••••••
Treatment ofCommunity-acquired bacterial pneumonia (cabp)•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Delafloxacin is a fluoroquinolone antibacterial drug which kills bacterial cells Label.

Mechanism of action

Delafloxacin inhibits the activity of bacterial DNA topoisomerase IV and DNA gyrase (topoisomerase II) Label. This interferes with bacterial DNA replication by preventing the relaxation of positive supercoils introduced as part of the elongation process 1. The resultant strain inhibits further elongation. Delafloxacin exerts concentration-dependent bacteriocidal activity Label.

TargetActionsOrganism
ADNA topoisomerase 4 subunit A
inhibitor
Escherichia coli (strain K12)
ADNA gyrase subunit A
inhibitor
Escherichia coli (strain K12)
Absorption

The median time to peak plasma concentration for orally administered Delafloxacin is 0.75 (0.5-4.0) hours after a single dose and 1.00 (0.5-6.0) hours for steady state dosing Label. The median time to peak plasma concentration for intravenously administered Delafloxacin is 1.00 (1.0-1.2) hours for a single dose and 1.0 (1.0-1.0) hour for steady state dosing. The absolute bioavailability for orally administed Delafloxacin is 58.8%.

Volume of distribution

The steady sate volume of distrubution of Delafloxacin is 30-48 liters Label.

Protein binding

Delafloxacin is 84% bound to human plasma proteins Label. It primarily binds to serum albumin.

Metabolism

Delafoxacin is primarily metabolized via glucuronidation mediated by UDP glucuronosyltransferase 1-1, UDP-glucuronosyltransferase 1-3, and UDP-glucuronosyltransferase 2B15 Label. Less than 1% is metabolized via oxidation.

Route of elimination

After a single intravenous dose, 65% of Delafloxacin was excreted in the urine either unchanged or as glucuronide metabolites with 28% excreted unchanged in the feces Label. After a single oral dose, 50% of Delafloxacin was excreted in the urine either unchanged or as glucuronide metabolites with 48% excreted unchanged in the feces.

Half-life

The mean half life of elimination of Delafloxacin is 3.7 hours after a single intravenous administration Label. The mean half life of elimination for multple oral administrations is 4.2-8.5 hours.

Clearance

The mean total clearance of Delafloxacin is 16.3 liters per hour Label. Renal clearance accounts for 35-45% of total clearance.

Adverse Effects
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Toxicity

The most common adverse reactions noted with Delafloxacin were nausea (8%), diarrhea (8%), headache (3%), transaminase elevations (3%), and vomiting (2%) Label. Fluoroquinolones are associated with increased frequency of tendon rupture and tendonitis, increased risk of peipheral neuropathy, excacerbation of myasthenia gravis, and development of Clostridium difficile-associated diarrhea. Fluoroquinolones are also associated with an increased risk of central nervous system reactions (CNS), including: convulsions and increased intracranial pressure (including pseudotumor cerebri) and toxic psychosis. Fluoroquinolones may also cause CNS reactions of nervousness, agitation, insomnia, anxiety, nightmares, paranoia, dizziness, confusion, tremors, hallucinations, depression, and suicidal thoughts or acts.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbacavirAbacavir may decrease the excretion rate of Delafloxacin which could result in a higher serum level.
AbemaciclibAbemaciclib may decrease the excretion rate of Delafloxacin which could result in a higher serum level.
AbrocitinibThe metabolism of Abrocitinib can be increased when combined with Delafloxacin.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Delafloxacin.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Delafloxacin.
Food Interactions
  • Avoid multivalent ions. Separate the administration of multivalent cations from delafloxacin by at least 6 hours before or 2 hours after delafloxacin.
  • Take separate from antacids. The administration of antacids should be separated from delafloxacin by at least 6 hours before or 2 hours after delafloxacin.
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Delafloxacin meglumineN7V53U4U4T352458-37-8AHJGUEMIZPMAMR-WZTVWXICSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BaxdelaTablet450 mg/1OralMelinta Therapeutics, LLC2017-06-19Not applicableUS flag
BaxdelaInjection, powder, lyophilized, for solution300 mg/10.5mLIntravenousMelinta Therapeutics, LLC2017-06-19Not applicableUS flag
QuofenixTablet450 mgOralA. Menarini Industrie Farmaceutiche Riunite s.r.l.2020-12-16Not applicableEU flag
QuofenixTablet450 mgOralA. Menarini Industrie Farmaceutiche Riunite s.r.l.2020-12-16Not applicableEU flag
QuofenixTablet450 mgOralA. Menarini Industrie Farmaceutiche Riunite s.r.l.2020-12-16Not applicableEU flag

Categories

ATC Codes
J01MA23 — Delafloxacin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Fluoroquinolones / Chloroquinolines / Aminoquinolines and derivatives / Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Polyhalopyridines / Aminopyridines and derivatives / Benzenoids
show 18 more
Substituents
1,2-aminoalcohol / Alcohol / Amine / Amino acid / Amino acid or derivatives / Aminopyridine / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Pseudomonas aeruginosa
  • Streptococcus pyogenes
  • Streptococcus agalactiae
  • Escherichia coli
  • Staphylococcus aureus
  • Enterococcus faecalis
  • Staphylococcus lugdunensis
  • Streptococcus anginosus
  • Proteus mirabilis
  • Enterobacter cloacae
  • Klebsiella pneumoniae
  • Staphylococcus haemolyticus
  • Streptococcus dysgalactiae
  • Enterobacter aerogenes
  • Haemophilus parainfluenzae
  • Klebsiella oxytoca

Chemical Identifiers

UNII
6315412YVF
CAS number
189279-58-1
InChI Key
DYDCPNMLZGFQTM-UHFFFAOYSA-N
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)
IUPAC Name
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
SMILES
NC1=NC(N2C=C(C(O)=O)C(=O)C3=CC(F)=C(N4CC(O)C4)C(Cl)=C23)=C(F)C=C1F

References

General References
  1. 49. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 612-614). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
PubChem Compound
487101
PubChem Substance
347828270
ChemSpider
427049
RxNav
1927663
ChEMBL
CHEMBL2105637
ZINC
ZINC000003827556
PDBe Ligand
TE9
Wikipedia
Delafloxacin
PDB Entries
8c41
FDA label
Download (1.37 MB)
MSDS
Download (23.4 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Enrolling by InvitationTreatmentBone and Joint Infections / Endovascular Infection / Gastrointestinal Tract Infections / Genitourinary tract infection / Pulmonary Infections / Skin and Soft Tissue Infections (SSTIs)1
3CompletedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)1
3CompletedTreatmentSkin and skin structure infections / Skin and Subcutaneous Tissue Bacterial Infections1
3CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections1
3TerminatedTreatmentNeisseria Gonorrhoeae Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous300 mg/10.5mL
TabletOral450 mg/1
Injection, powder, for solutionIntravenous300 MG
TabletOral450 MG
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7635773No2009-12-222029-03-13US flag
US8410077No2013-04-022029-03-13US flag
US9200088No2015-12-012029-03-13US flag
US9493582No2016-11-152033-02-27US flag
US8969569No2015-03-032025-10-07US flag
US8252813No2012-08-282026-10-02US flag
US9539250No2017-01-102025-10-07US flag
US8648093No2014-02-112025-10-07US flag
US8871938No2014-10-282029-09-23US flag
US7728143No2010-06-012027-11-20US flag
US8273892No2012-09-252026-08-06US flag
US8497378No2013-07-302029-12-28US flag
US9750822No2017-09-052029-03-13US flag
USRE46617No2017-11-282029-12-28US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0699 mg/mLALOGPS
logP1.67ALOGPS
logP2.56Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)5.62Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area119.99 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity101.33 m3·mol-1Chemaxon
Polarizability38.42 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-0000900000-1f5fe2a5103e42bc9d11
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009200000-9ba152608f2c0a2e7614
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009200000-62cfec5412cff07f75e4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0000900000-4aa6cb98abdfd17e5faa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-4009100000-fa3897dbe53c5a456986
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0009500000-02452396ae937a4983fe
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-195.1186
predicted
DeepCCS 1.0 (2019)
[M+H]+197.51418
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.42671
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA topoisomerase 4 subunit A
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule. MukB stimulates th...
Gene Name
parC
Uniprot ID
P0AFI2
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
83830.455 Da
Details2. DNA gyrase subunit A
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Identical protein binding
Specific Function
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
Gene Name
gyrA
Uniprot ID
P0AES4
Uniprot Name
DNA gyrase subunit A
Molecular Weight
96962.63 Da

Enzymes

Details1. UDP-glucuronosyltransferase 1-1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
Details2. UDP-glucuronosyltransferase 1-3
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
Details3. UDP-glucuronosyltransferase 2B15
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
Details4. Cytochrome P450 2E1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
Details5. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
Details6. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Delafloxacin FDA label [Link]

Carriers

Details1. Serum albumin
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Transporters

Details1. ATP-binding cassette sub-family B member 5
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Efflux transmembrane transporter activity
Specific Function
Drug efflux transporter present in a number of stem cells that acts as a regulator of cellular differentiation. Able to mediate efflux from cells of the rhodamine dye and of the therapeutic drug do...
Gene Name
ABCB5
Uniprot ID
Q2M3G0
Uniprot Name
ATP-binding cassette sub-family B member 5
Molecular Weight
138639.48 Da
Details2. ATP-binding cassette sub-family G member 2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da

Drug created at October 20, 2016 21:03 / Updated at February 21, 2021 18:53