LFX

(3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Created: 2009-10-20
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count46
Chiral Atom Count1
Bond Count49
Aromatic Bond Count6
2D diagram of LFX

Chemical Component Summary

Name(3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
SynonymsLevofloxacin
Systematic Name (OpenEye OEToolkits)n/a
FormulaC18 H20 F N3 O4
Molecular Weight361.368
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs11.02O=C(O)C=1C(=O)c4c2N(C=1)C(COc2c(N3CCN(C)CC3)c(F)c4)C
SMILESCACTVS3.352C[CH]1COc2c(N3CCN(C)CC3)c(F)cc4C(=O)C(=CN1c24)C(O)=O
SMILESOpenEye OEToolkits1.7.0CC1COc2c3c(cc(c2N4CCN(CC4)C)F)C(=O)C(=CN31)C(=O)O
Canonical SMILESCACTVS3.352 C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc4C(=O)C(=CN1c24)C(O)=O
Canonical SMILESOpenEye OEToolkits1.7.0 C[C@H]1COc2c3c(cc(c2N4CCN(CC4)C)F)C(=O)C(=CN31)C(=O)O
InChIInChI1.03 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
InChIKeyInChI1.03 GSDSWSVVBLHKDQ-JTQLQIEISA-N

Drug Info: DrugBank

DrugBank IDDB01137 
NameLevofloxacin
Groups
  • approved
  • investigational
DescriptionLevofloxacin is a fluoroquinolone antibiotic and the optical S-(-) isomer of racemic [ofloxacin].[A190663] It reportedly carries 8 to 128-fold more activity against both gram-negative and gram-positive bacteria compared to R-(+)-ofloxacin[A190663] and remains stereochemically stable following administration (i.e. it does not invert to the inactive isomer).[L11638] Levofloxacin, along with other quinolones such as [gatifloxacin] and [moxifloxacin], is a member of the third generation of fluoroquinolones, colloquially referred to as the "respiratory quinolones" due to improved activity against gram-positive bacteria commonly implicated in respiratory infections.[A31453,A190756] Levofloxacin was first approved by the FDA in 1996, and was approved in Canada and several South American countries soon after.[A190663]
Synonyms
  • (S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acid
  • Levofloxacin anhydrous
  • (S)-Ofloxacin
  • L-Ofloxacin
  • Levofloxacinum
Brand Names
  • Levaquin 25mg/ml
  • Sandoz Levofloxacin
  • Quinsair
  • Riva-levofloxacin
  • Levaquin 750mg
IndicationIn oral and intravenous formulations, levofloxacin is indicated in adults for the treatment of various infections caused by susceptible bacteria, including infections of the upper respiratory tract, lower respiratory tract, skin, skin structures, urinary tract, and prostate.[L11638,L11692] The oral formulation is also indicated in both adults and children 6 months of age and older for the post-exposure management of inhalational anthrax caused by _Bacillus anthracis_ and for the treatment and/or prophylaxis of plague caused by _Yersinia pestis_.[L11638] In its ophthalmic formulation, levofloxacin is indicated for the treatment of bacterial conjunctivitis caused by susceptible organisms.[L11641] An inhalational solution available in Canada is indicated for the management of cystic fibrosis patients aged 18 years or older with chronic pulmonary _Pseudomonas aeruginosa_ infections.[L11689]
Categories
  • Alimentary Tract and Metabolism
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Anti-Infective Agents, Urinary
  • Antibacterials for Systemic Use
ATC-Code
  • J01MA12
  • A02BD10
  • J01RA05
  • S01AE05
CAS number100986-85-4

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA gyrase subunit AMTDSIQSSITPVNIEEELKSSYLDYAMSVIVGRALPDVRDGLKPVHRRVL...unknowninhibitor
DNA topoisomerase 4 subunit AMTNINYEGIEQMPLRTFTEKAYLNYSMYVIMDRALPFIGDGLKPVQRRIV...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknowninhibitor
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownsubstrate
P-glycoprotein 1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 149096, 6956357
ChEMBL CHEMBL33
ChEBI CHEBI:63598
CCDC/CSD CUYCEF01, LICWOM, YUJNUM01, LICWOM01, CUYCEF, YUJPAU01, YUJNUM02, CUYCEF02, OZOPIF, LAPMUO
COD 4502707