CAS 100986-85-4|CAS 138199-71-0|Leroxacin|(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid|Tavanic|Levokac...

General Information

Structure

Molecular Formula

C₁₈H₂₀FN₃O₄

Molecular Mass

361.3675032

Exact Mass

361.14378436

Charge

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-/m0/s1

InChIKey

GSDSWSVVBLHKDQ-JTQLQIEISA-N

Canonic Smiles

CN1CCN(CC1)c1c(F)cc2c3c1OC[C@@H](n3cc(c2=O)C(=O)O)C

Isomeric Smiles

Fc1c(N2CCN(CC2)C)c2OC[C@@H](n3c2c(c1)c(=O)c(c3)C(=O)O)C

Calculated Properties

JChem

Acid pKa

5.4470572

H Acceptors

H Donor

LogD (pH = 5.5)

0.616237

LogD (pH = 7.4)

-0.2825112

Log P

0.65427977

Molar Refractivity

94.9359

Polarizability

34.82272

Polar Surface Area

73.32

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

-0.02

LOG S

-2.4

Solubility (Water)

1.44e+00 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

LeroxacinTavanicLevokacinLevoxCravit OphthalmicElequineLevaquinMosardalCravitQuixinReskuinLesacinIquixLevoxacinFloxelVolequinNofaxin

IUPAC name

(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0⁵,¹³]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

Synonyms

levofloxacinLevofloxacinL-OfloxacinTavanicLevaquinLevofloxacin Hydrate(-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid HemihydrateLevofloxacin HemihydrateDynaquinLevofloxacin(-)-Ofloxacin

IUPAC Traditional name

levofloxacin

Names and Identifiers

Registration numbers

PubChem SID

2485706046505134160964471

MDL Number

MFCD00865049

Beilstein Number

7327015

CAS Number

100986-85-4138199-71-0

PubChem CID

149096

Registration numbers

Properties

Product Information

Salt Data

Free Base

Empirical Formula (Hill Notation)

C18H20FN3O4

Purity

≥98.0% (HPLC)

Certificate of Analysis

Download link

Pharmacology Properties

Gene Information

human ... KCNH1(3756)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01137

Drug Groups

approved; investigational

Description

A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. [PubChem]

Indication

For the treatment of bacterial conjunctivitis caused by susceptible strains of the following organisms: Corynebacterium species, Staphylococus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus (Groups C/F/G), Viridans group streptococci, Acinetobacter lwoffii, Haemophilus influenzae, Serratia marcescens.

Pharmacology

Levofloxacin, a fluoroquinolone antiinfective, is the optically active L-isomer of ofloxacin. Levofloxacin is used to treat bacterial conjunctivitis, sinusitis, chronic bronchitis, community-acquired pneumonia and pneumonia caused by penicillin-resistant strains of Streptococcus pneumoniae, skin and skin structure infections, complicated urinary tract infections and acute pyelonephritis.

Toxicity

Side effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans.

Absorption

Absorption of ofloxacin after single or multiple doses of 200 to 400 mg is predictable, and the amount of drug absorbed increases proportionately with the dose.

Half Life

6-8 hours

Protein Binding

24-38% (to plasma proteins)

Elimination

Mainly excreted as unchanged drug in the urine.

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1940

Research Area: Infection
Biological Activity:
Levofloxacin(Levaquin) is a synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase. Levofloxacin, like other fluoroquinolones, inhibits the A subunits of DNA gyrase, two subunits encoded by the gyrA gene. This results in strand breakage on a bacterial chromosome, supercoiling, and resealing; DNA replication and transcription is inhibited. [1]

TRC

L360000

S-(-)-Form of Ofloxacin. An antibiotic used against gram-negative organisms.

Sigma Aldrich

28266

Other Notes
Antibiotic against bacterial respiratory tract infections5,6
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 28266.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Application
Levofloxacin is a broad-spectrum antibiotic used in pharmacokinetic 1, antibiotic resistance 2 , and resistance prevention 3studies.
Biochem/physiol Actions
Levofloxacin is active against Gram-positive and Gram-negative bacteria. It inhibits DNA gyrase (type II topoisomerase) and topoisomerase IV, 4 thereby inhibiting cell division.

Molecule Details

References

PubChem Literature

From Data Sources

• http://www.drugbank.ca/drugs/DB01137

• Hwang, D.G., et al.: Br. J. Ophthalmol., 87, 1004 (1992)

• North, D.S., et al.: Pharmacotherapy, 18, 915 (1992)

• Kato, M., et al.: Arzneim.-Forsch., 42, 365 (1992)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Brand Name

LeroxacinTavanicLevokacinLevoxCravit OphthalmicElequineLevaquinMosardalCravitQuixinReskuinLesacinIquixLevoxacinFloxelVolequinNofaxin

IUPAC name

Synonyms

IUPAC Traditional name

levofloxacin

Registration numbers

PubChem SID

2485706046505134160964471

MDL Number

MFCD00865049

Beilstein Number

7327015

CAS Number

100986-85-4138199-71-0

PubChem CID

149096

Molecule Details

DrugBank

DB01137

Drug Groups

approved; investigational

Description

A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. [PubChem]

Indication

Pharmacology

Toxicity

Side effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans.

Absorption

Absorption of ofloxacin after single or multiple doses of 200 to 400 mg is predictable, and the amount of drug absorbed increases proportionately with the dose.

Half Life

6-8 hours

Protein Binding

24-38% (to plasma proteins)

Elimination

Mainly excreted as unchanged drug in the urine.

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals