D-Levofloxacin

Identification

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Name
D-Levofloxacin
Accession Number
DB03034  (EXPT03256)
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
Synonyms
  • D-Ofloxacin
  • R-Ofloxacin
External IDs
DR-3354
Categories
UNII
36OPE0O92Z
CAS number
100986-86-5
Weight
Average: 361.3675
Monoisotopic: 361.143784348
Chemical Formula
C18H20FN3O4
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[7.3.1.0⁵,¹³]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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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
AgmatineThe serum concentration of Agmatine can be increased when it is combined with D-Levofloxacin.
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.
CimetidineThe serum concentration of Cimetidine 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.
DalfampridineThe serum concentration of Dalfampridine can be increased when it is combined with D-Levofloxacin.
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with D-Levofloxacin.
DopamineThe serum concentration of Dopamine can be increased when it is combined with D-Levofloxacin.
EpinephrineThe serum concentration of Epinephrine can be increased when it is combined with D-Levofloxacin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
452723
PubChem Substance
46506037
ChemSpider
398760
BindingDB
50226409
ChEMBL
CHEMBL420937
HET
XED
PDB Entries
2bml

Clinical Trials

Clinical Trials
Not Available

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
logP0.65ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.45ChemAxon
pKa (Strongest Basic)6.2ChemAxon
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0269000000-b5fad3da16d586576b72

Taxonomy

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
Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Benzoxazine / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 17:32