CHEBI:63598 - levofloxacin

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ChEBI Name levofloxacin
ChEBI ID CHEBI:63598
Definition An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:6440
Supplier Information ChemicalBook:CB93569251, ChemicalBook:CB4122906, ChemicalBook:CB72567531, eMolecules:494498, Selleckchem:Levofloxacin(Levaquin), ZINC000000538273
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Levofloxacin, sold under the brand name Levaquin among others, is a broad-spectrum antibiotic of the fluoroquinolone drug class. It is the left-handed isomer of the medication ofloxacin. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori (in combination with other medications), urinary tract infections, Legionnaires' disease, chronic bacterial prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. It is available by mouth, intravenously, and in eye drop form. Common side effects include nausea, diarrhea, and trouble sleeping. A warning concerning all fluoroquinolones was issued in 2016: "An FDA safety review has shown that fluoroquinolones when used systemically (i.e. tablets, capsules, and injectable) are associated with disabling and potentially permanent serious adverse effects that can occur together. These adverse effects can involve the tendons, muscles, joints, nerves, and central nervous system." Other serious side effects may include tendon rupture, tendon inflammation, seizures, psychosis, and potentially permanent peripheral nerve damage. Tendon damage may appear months after treatment is completed. People may also sunburn more easily. In people with myasthenia gravis, muscle weakness and breathing problems may worsen. While use during pregnancy is not recommended, risk appears to be low. The use of other medications in this class appear to be safe while breastfeeding; however, the safety of levofloxacin is unclear. Levofloxacin was patented in 1985 and approved for medical use in the United States in 1996. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the 251st most commonly prescribed medication in the United States, with more than 1 million prescriptions.
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Formula C18H20FN3O4
Net Charge 0
Average Mass 361.373
Monoisotopic Mass 361.14378
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
SMILES C[C@H]1COC2=C(N3CCN(C)CC3)C(F)=CC3=C2N1C=C(C(O)=O)C3=O
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood plasma (BTO:0000118). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
antibacterial drug
A drug used to treat or prevent bacterial infections.
topoisomerase IV inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase IV, which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via quinolone antibiotic )
(via heterocyclic antibiotic )
(via fluoroquinolone antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing levofloxacin (CHEBI:63598) has role antibacterial drug (CHEBI:36047)
levofloxacin (CHEBI:63598) has role DNA synthesis inhibitor (CHEBI:59517)
levofloxacin (CHEBI:63598) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
levofloxacin (CHEBI:63598) has role topoisomerase IV inhibitor (CHEBI:53559)
levofloxacin (CHEBI:63598) is a 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 (CHEBI:194135)
levofloxacin (CHEBI:63598) is a fluoroquinolone antibiotic (CHEBI:87211)
levofloxacin (CHEBI:63598) is a quinolone antibiotic (CHEBI:86324)
levofloxacin (CHEBI:63598) is conjugate acid of levofloxacin(1−) (CHEBI:231553)
levofloxacin (CHEBI:63598) is enantiomer of dextrofloxacin (CHEBI:46577)
Incoming ofloxacin (CHEBI:7731) has part levofloxacin (CHEBI:63598)
levofloxacin(1−) (CHEBI:231553) is conjugate base of levofloxacin (CHEBI:63598)
dextrofloxacin (CHEBI:46577) is enantiomer of levofloxacin (CHEBI:63598)
IUPAC 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
INNs Sources
levofloxacin KEGG DRUG
levofloxacine ChemIDplus
levofloxacino ChemIDplus
levofloxacinum ChemIDplus
Synonyms Sources
(−)-ofloxacin ChEBI
(-)-Ofloxacin ChemIDplus
(3S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid ChEBI
(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 ChEBI
(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 ChemIDplus
(S)-ofloxacin ChemIDplus
DR 3355 ChEBI
DR-3355 ChEBI
L-ofloxacin DrugBank
Ofloxacin S-(-)-form KEGG COMPOUND
S-(−)-ofloxacin ChEBI
Manual Xrefs Databases
1569 DrugCentral
1899 VSDB
C07660 KEGG COMPOUND
D08120 KEGG DRUG
DB01137 DrugBank
HMDB0001929 HMDB
Levofloxacin Wikipedia
LFX PDBeChem
LSM-5270 LINCS
View more database links
Registry Numbers Types Sources
100986-85-4 CAS Registry Number ChemIDplus
5385660 Reaxys Registry Number Reaxys
Citations
Qin X, Zhong X, Wang B, Wang G, Liu F, Weng L (2023)
Fractionation of levofloxacin and ofloxacin during their transport in NOM-goethite: Batch and column studies.
Environmental pollution (Barking, Essex : 1987) 316, 120542 [PubMed:36328279]
[show Abstract]
Kaul G, Karale UB, Akhir A, Shukla M, Saxena D, Rode HB, Chopra S (2022)
Pyrvinium pamoate potentiates levofloxacin against levofloxacin-resistant Staphylococcus aureus.
Future microbiology 17, 1475-1486 [PubMed:36314364]
[show Abstract]
Schwarz C, Procaccianti C, Costa L, Brini R, Friend R, Caivano G, Sadafi H, Mussche C, Schwenck N, Hahn M, Murgia X, Bianco F (2022)
Differential Performance and Lung Deposition of Levofloxacin with Different Nebulisers Used in Cystic Fibrosis.
International journal of molecular sciences 23, 9597 [PubMed:36076992]
[show Abstract]
Ben Ayed A, Akrout I, Albert Q, Greff S, Simmler C, Armengaud J, Kielbasa M, Turbé-Doan A, Chaduli D, Navarro D, Bertrand E, Faulds CB, Chamkha M, Maalej A, Zouari-Mechichi H, Sciara G, Mechichi T, Record E (2022)
Biotransformation of the Fluoroquinolone, Levofloxacin, by the White-Rot Fungus Coriolopsis gallica.
Journal of fungi (Basel, Switzerland) 8, 965 [PubMed:36135690]
[show Abstract]
Wang Y, Li C, Wang J, Bai N, Zhang H, Chi Y, Cai Y (2022)
The Efficacy of Colistin Combined with Amikacin or Levofloxacin against Pseudomonas aeruginosa Biofilm Infection.
Microbiology spectrum 10, e0146822 [PubMed:36102678]
[show Abstract]
Le-Deygen IM, Safronova AS, Kolmogorov IM, Skuredina AA, Kudryashova EV (2022)
The Influence of Lipid Matrix Composition on the Microenvironment of Levofloxacin in Liposomal Forms.
Russian journal of bioorganic chemistry 48, 710-719 [PubMed:36119964]
[show Abstract]
Kaczmarek M, Staninski K, Stodolny M (2021)
New chemiluminescent method of levofloxacin and ofloxacin determination based on terbium (III)-sensitized fluoroquinolone-KBrO3 reaction.
Luminescence : the journal of biological and chemical luminescence 36, 1945-1952 [PubMed:34323366]
[show Abstract]
Ornik-Cha A, Wilhelm J, Kobylka J, Sjuts H, Vargiu AV, Malloci G, Reitz J, Seybert A, Frangakis AS, Pos KM (2021)
Structural and functional analysis of the promiscuous AcrB and AdeB efflux pumps suggests different drug binding mechanisms.
Nature communications 12, 6919 [PubMed:34824229]
[show Abstract]
Veselkov DA, Laponogov I, Pan XS, Selvarajah J, Skamrova GB, Branstrom A, Narasimhan J, Prasad JV, Fisher LM, Sanderson MR (2016)
Structure of a quinolone-stabilized cleavage complex of topoisomerase IV from Klebsiella pneumoniae and comparison with a related Streptococcus pneumoniae complex.
Acta crystallographica. Section D, Structural biology 72, 488-496 [PubMed:27050128]
[show Abstract]
Blower TR, Williamson BH, Kerns RJ, Berger JM (2016)
Crystal structure and stability of gyrase-fluoroquinolone cleaved complexes from Mycobacterium tuberculosis.
Proceedings of the National Academy of Sciences of the United States of America 113, 1706-1713 [PubMed:26792525]
[show Abstract]
Laponogov I, Veselkov DA, Crevel IM, Pan XS, Fisher LM, Sanderson MR (2013)
Structure of an 'open' clamp type II topoisomerase-DNA complex provides a mechanism for DNA capture and transport.
Nucleic acids research 41, 9911-9923 [PubMed:23965305]
[show Abstract]
Rimbara E, Noguchi N, Kawai T, Sasatsu M (2012)
Fluoroquinolone resistance in Helicobacter pylori: role of mutations at position 87 and 91 of GyrA on the level of resistance and identification of a resistance conferring mutation in GyrB.
Helicobacter 17, 36-42 [PubMed:22221614]
[show Abstract]
Sonnet P, Izard D, Mullié C (2012)
Prevalence of efflux-mediated ciprofloxacin and levofloxacin resistance in recent clinical isolates of Pseudomonas aeruginosa and its reversal by the efflux pump inhibitors 1-(1-naphthylmethyl)-piperazine and phenylalanine-arginine-β-naphthylamide.
International journal of antimicrobial agents 39, 77-80 [PubMed:21974858]
[show Abstract]
Fukuda Y, Takahata M, Sugiura Y, Shinmura Y, Nomura N (2012)
In vitro pharmacodynamic evaluation of garenoxacin against quinolone-resistant Streptococcus pneumoniae.
International journal of antimicrobial agents 39, 163-167 [PubMed:22088660]
[show Abstract]
Khawcharoenporn T, Vasoo S, Ward E, Singh K (2012)
High rates of quinolone resistance among urinary tract infections in the ED.
The American journal of emergency medicine 30, 68-74 [PubMed:21075586]
[show Abstract]
Cuadrado-Lavín A, Salcines-Caviedes JR, Carrascosa MF, Mellado P, Monteagudo I, Llorca J, Cobo M, Campos MR, Ayestarán B, Fernández-Pousa A, González-Colominas E (2012)
Antimicrobial susceptibility of Helicobacter pylori to six antibiotics currently used in Spain.
The Journal of antimicrobial chemotherapy 67, 170-173 [PubMed:21965436]
[show Abstract]
Laponogov I, Pan XS, Veselkov DA, McAuley KE, Fisher LM, Sanderson MR (2010)
Structural basis of gate-DNA breakage and resealing by type II topoisomerases.
PloS one 5, e11338 [PubMed:20596531]
[show Abstract]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM (2009)
Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression.
Nature 457, 910-914 [PubMed:19212411]
[show Abstract]
Zhou ZL, Yang M, Yu XY, Peng HY, Shan ZX, Chen SZ, Lin QX, Liu XY, Chen TF, Zhou SF, Lin SG (2007)
A rapid and simple high-performance liquid chromatography method for the determination of human plasma levofloxacin concentration and its application to bioequivalence studies.
Biomedical chromatography : BMC 21, 1045-1051 [PubMed:17549677]
[show Abstract]
Martínez Martínez MS, Gandarillas CI, Martínez Lanao J, Sánchez Navarro A (2005)
Comparative study of the disposition of levofloxacin, netilmicin and cefepime in the isolated rat lung.
The Journal of pharmacy and pharmacology 57, 861-867 [PubMed:15969945]
[show Abstract]
Bielecka-Grzela S, Klimowicz A (2003)
Evaluation of ofloxacin penetration into the skin after a single oral dose assessed by cutaneous microdialysis.
Polish journal of pharmacology 55, 613-618 [PubMed:14581720]
[show Abstract]
Chow AT, Chen A, Lattime H, Morgan N, Wong F, Fowler C, Williams RR (2002)
Penetration of levofloxacin into skin tissue after oral administration of multiple 750 mg once-daily doses.
Journal of clinical pharmacy and therapeutics 27, 143-150 [PubMed:11975700]
[show Abstract]
Ozawa TT, Valadez T (2002)
Clostridium difficile infection associated with levofloxacin treatment.
Tennessee medicine : journal of the Tennessee Medical Association 95, 113-115 [PubMed:11898264]
[show Abstract]
Budanov SV, Smirnova LB (2001)
[Levofloxacin (Tavanic)--a novel quinolone of the III generation. Antimicrobial activity, pharmacokinetics, clinical significance].
Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] 46, 31-38 [PubMed:11558453]
Berning SE, Cherry TA, Iseman MD (2001)
Novel treatment of meningitis caused by multidrug-resistant Mycobacterium tuberculosis with intrathecal levofloxacin and amikacin: case report.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 32, 643-646 [PubMed:11181130]
[show Abstract]
Kalbermatter V, Bagilet D, Diab M, Javkin E (2000)
[Oral levofloxacin versus intravenous ceftriaxone and amoxicillin/clavulanic acid in the treatment of community-acquired pneumonia that requires hospitalization].
Medicina clinica 115, 561-563 [PubMed:11141388]
[show Abstract]
Isogai E, Isogai H, Hayashi S, Kubota T, Kimura K, Fujii N, Ohtani T, Sato K (2000)
Effect of antibiotics, levofloxacin and fosfomycin, on a mouse model with Escherichia coli O157 infection.
Microbiology and immunology 44, 89-95 [PubMed:10803495]
[show Abstract]
Norrby SR (1999)
Levofloxacin.
Expert opinion on pharmacotherapy 1, 109-119 [PubMed:11249554]
[show Abstract]
Nicodemo AC, Robledo JA, Jasovich A, Neto W (1998)
A multicentre, double-blind, randomised study comparing the efficacy and safety of oral levofloxacin versus ciprofloxacin in the treatment of uncomplicated skin and skin structure infections.
International journal of clinical practice 52, 69-74 [PubMed:9624783]
[show Abstract]
Fish DN, Chow AT (1997)
The clinical pharmacokinetics of levofloxacin.
Clinical pharmacokinetics 32, 101-119 [PubMed:9068926]
[show Abstract]
Yoshimura T, Kurita C, Usami E, Nakao T, Watanabe S, Kobayashi J, Yamazaki F, Nagai H (1996)
Immunomodulatory action of levofloxacin on cytokine production by human peripheral blood mononuclear cells.
Chemotherapy 42, 459-464 [PubMed:8957581]
[show Abstract]
Oya S, Takemoto A, Hosaka K, Kudou Y, Arakawa M (1995)
[In vitro antimicrobial activity of a new quinolone, levofloxacin, against atypical mycobacteria].
Kekkaku : [Tuberculosis] 70, 615-619 [PubMed:8656585]
[show Abstract]
Tanaka M, Otsuki M, Une T, Nishino T (1990)
In-vitro and in-vivo activity of DR-3355, an optically active isomer of ofloxacin.
The Journal of antimicrobial chemotherapy 26, 659-666 [PubMed:2079448]
[show Abstract]
Last Modified
11 June 2024