NAV

D-Levofloxacin

Identification

Generic Name
D-Levofloxacin
DrugBank Accession Number
DB03034
Background

A synthetic fluoroquinolone (FLUOROQUINOLONES) antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 361.3675
Monoisotopic: 361.143784348
Chemical Formula
C18H20FN3O4
Synonyms
  • D-Ofloxacin
  • R-Ofloxacin
External IDs
  • DR-3354
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAutolysinNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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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AmantadineThe serum concentration of Amantadine can be increased when it is combined with D-Levofloxacin.
CholineThe serum concentration of Choline can be increased when it is combined with D-Levofloxacin.
Choline salicylateThe serum concentration of Choline salicylate can be increased when it is combined with D-Levofloxacin.
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with D-Levofloxacin.
ClofarabineThe serum concentration of Clofarabine can be increased when it is combined with D-Levofloxacin.
Food Interactions
Not Available

Categories

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 / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Benzoxazines / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / N-methylpiperazines
show 15 more
Substituents
1,4-diazinane / Alkyl aryl ether / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
36OPE0O92Z
CAS number
100986-86-5
InChI Key
GSDSWSVVBLHKDQ-SNVBAGLBSA-N
InChI
InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m1/s1
IUPAC Name
(2R)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5,7,9(13),11-tetraene-11-carboxylic acid
SMILES
C[C@@H]1COC2=C(N3CCN(C)CC3)C(F)=CC3=C2N1C=C(C(O)=O)C3=O

References

General References
Not Available
PubChem Compound
452723
PubChem Substance
46506037
ChemSpider
398760
BindingDB
50226409
ChEMBL
CHEMBL420937
ZINC
ZINC000000537891
PDBe Ligand
XED
PDB Entries
2bml

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP-0.02ALOGPS
logP0.09Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.35Chemaxon
pKa (Strongest Basic)6.72Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area73.32 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity94.94 m3·mol-1Chemaxon
Polarizability36.75 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9545
Blood Brain Barrier-0.9659
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.7489
CYP450 2C9 substrateNon-substrate0.8468
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6386
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9268
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7726
Ames testAMES toxic0.7844
CarcinogenicityNon-carcinogens0.9033
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.1639 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8402
hERG inhibition (predictor II)Non-inhibitor0.866
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0269000000-b5fad3da16d586576b72
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0009000000-36259e1f93e7f0591ff8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0029000000-575d0b555ec70a134ced
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-a4319ee2062d2e84d33e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0292-0059000000-d39f6e7bcbdc53f172d1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-0019000000-52f593d297a6cb46de27
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pic-0398000000-41f0181effb1e475d616
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]-178.48776
predicted
DeepCCS 1.0 (2019)
[M+H]+180.84575
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.3936
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Autolysin
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
N-acetylmuramoyl-l-alanine amidase activity
Specific Function
Autolysins are involved in some important biological processes such as cell separation, cell-wall turnover, competence for genetic transformation, formation of the flagella and sporulation. Autolys...
Gene Name
lytA
Uniprot ID
P06653
Uniprot Name
Autolysin
Molecular Weight
36544.235 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52