Levofloxacin
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Basic Info
| Common Name | Levofloxacin(F04702) |
| 2D Structure | |
| Description | Levofloxacin is a synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. Levofloxacin is marketed by Ortho-McNeil under the trade name Levaquin. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin. |
| FRCD ID | F04702 |
| CAS Number | 100986-85-4 |
| PubChem CID | 149096 |
| Formula | C18H20FN3O4 |
| IUPAC Name | None |
| InChI Key | GSDSWSVVBLHKDQ-JTQLQIEISA-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-/m0/s1 |
| Canonical SMILES | CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O |
| Isomeric SMILES | C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O |
| Wikipedia | Levofloxacin |
| Synonyms |
LEVOFLOXACIN
100986-85-4
Levaquin
Quixin
Iquix
Levofloxacine
Cravit
Tavanic
(-)-Ofloxacin
Ofloxacin S-(-)-form
|
| Classifies |
Predicted: Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | Quinoline carboxylic acids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Quinoline carboxylic acids |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Quinoline-3-carboxylic acid - Fluoroquinolone - N-arylpiperazine - Aminoquinoline - Haloquinoline - Dihydroquinolone - Benzoxazine - Dihydroquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Tertiary aliphatic/aromatic amine - Dialkylarylamine - N-alkylpiperazine - N-methylpiperazine - Alkyl aryl ether - Benzenoid - Pyridine - Aryl fluoride - Piperazine - Aryl halide - 1,4-diazinane - Vinylogous amide - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Amino acid or derivatives - Amino acid - Azacycle - Oxacycle - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organonitrogen compound - Organic nitrogen compound - Amine - Organic oxygen compound - Organooxygen compound - Organopnictogen compound - Organic oxide - Organofluoride - Hydrocarbon derivative - Organohalogen compound - Aromatic heteropolycyclic compound |
| 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 361.373 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 2 |
| Complexity | 634 |
| Monoisotopic Mass | 361.144 |
| Exact Mass | 361.144 |
| XLogP | -0.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 26 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9659 |
| Human Intestinal Absorption | HIA+ | 0.9545 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Substrate | 0.7862 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8782 |
| Non-inhibitor | 0.8383 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7489 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7248 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8468 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.6386 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9268 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7726 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8402 |
| Non-inhibitor | 0.8660 | |
| AMES Toxicity | AMES toxic | 0.7844 |
| Carcinogens | Non-carcinogens | 0.9033 |
| Fish Toxicity | High FHMT | 0.9975 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9407 |
| Honey Bee Toxicity | Low HBT | 0.8853 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7916 |
| Carcinogenicity (Three-class) | Non-required | 0.6211 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5105 | LogS |
| Caco-2 Permeability | 1.1297 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1639 | LD50, mol/kg |
| Fish Toxicity | 1.0677 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6862 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Enumerating Antibiotic Susceptibility Patterns of Pseudomonas aeruginosa Isolatedfrom Different Sources in Dhaka City. | Open Microbiol J | 2018 May 31 | 29997702 |
| Presence of antibiotic residues in various environmental compartments of Shandongprovince in eastern China: Its potential for resistance development andecological and human risk. | Environ Int | 2018 May | 29501851 |
| Establishment and Validation of Galleria mellonella as a Novel Model Organism To Study Mycobacterium abscessus Infection, Pathogenesis, and Treatment. | Antimicrob Agents Chemother | 2018 Mar 27 | 29437630 |
| When antibiotics turn toxic. | Nature | 2018 Mar 22 | 29565407 |
| Toxicological assessment of hospital wastewater in different treatment processes. | Environ Sci Pollut Res Int | 2018 Mar | 26099595 |
| Antibiotic Resistance in Salmonella from Retail Foods of Animal Origin and ItsAssociation with Disinfectant and Heavy Metal Resistance. | Microb Drug Resist | 2018 Jul/Aug | 29039715 |
| Development of Protective Immunity in New Zealand White Rabbits Challenged with Bacillus anthracis Spores and Treated with Antibiotics and Obiltoxaximab, a Monoclonal Antibody against Protective Antigen. | Antimicrob Agents Chemother | 2018 Feb | 29133571 |
| Species Distribution and Antimicrobial Profiles of Enterococcus spp. Isolatesfrom Kenyan Small and Medium Enterprise Slaughterhouses. | J Food Prot | 2018 Aug 3:1445-1449 | 30080119 |
| Listeria monocytogenes in raw milk, milking equipment and dairy workers:Molecular characterization and antimicrobial resistance patterns. | J Glob Antimicrob Resist | 2017 Sep | 28739228 |
| Gyrase A Mutations in Campylobacter Associated with Decreased Susceptibility toDifferent Fluoroquinolones. | J Food Prot | 2017 Oct 10:1863-1866 | 28994613 |
| Novel and Effective Therapeutic Regimens for Helicobacter pylori in an Era ofIncreasing Antibiotic Resistance. | Front Cell Infect Microbiol | 2017 May 5 | 28529929 |
| First Report in China on the Identification and Drug Sensitivity of Mycobacteriumelephantis Isolated from the Milk of a Cow with Mastitis. | Biomed Environ Sci | 2017 Jul | 28756809 |
| Distribution and Antimicrobial Susceptibility of Foodborne Salmonella Serovars inEight Provinces in China from 2007 to 2012 (Except 2009). | Foodborne Pathog Dis | 2017 Jul | 28375673 |
| Experimental study on the influence of low-frequency and low-intensity ultrasoundon the permeability of the Mycobacterium smegmatis cytoderm and potentiation withlevofloxacin. | Ultrason Sonochem | 2017 Jul | 28427611 |
| Measurement of levofloxacin in human plasma samples for a reliable and accessibledrug monitoring. | Clin Biochem | 2017 Jan | 27637364 |
| Combating Multidrug-Resistant Pathogens with Host-Directed NonantibioticTherapeutics. | Antimicrob Agents Chemother | 2017 Dec 21 | 29109161 |
| Antibiotic susceptibilities and prevalence of Methicillin resistantStaphylococcus aureus (MRSA) isolated from bovine milk in Pakistan. | Acta Trop | 2017 Dec | 28797802 |
| Arcobacter Isolation from Minced Beef Samples in Costa Rica. | J Food Prot | 2017 Apr 3:775-778 | 28371592 |
| N2 Gas Flushing Limits the Rise of Antibiotic-Resistant Bacteria in Bovine RawMilk during Cold Storage. | Front Microbiol | 2017 Apr 19 | 28469611 |
| Molecularly imprinted macroporous monoliths for solid-phase extraction: Effect ofpore size and column length on recognition properties. | J Chromatogr B Analyt Technol Biomed Life Sci | 2016 Sep 1 | 27433985 |
Targets
- General Function:
- Ubiquitin binding
- Specific Function:
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
- Gene Name:
- TOP2A
- Uniprot ID:
- P11388
- Molecular Weight:
- 174383.88 Da
- Mechanism of Action:
- 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.
References
- Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
- General Function:
- Monovalent cation:proton antiporter activity
- Specific Function:
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acyclovir, ganciclovir and also the zwitterionic cephalosporin, cephalexin and cephradin. Seems to also play a role in the uptake of oxaliplatin (a new platinum anticancer agent). Able to transport paraquat (PQ or N,N-dimethyl-4-4'-bipiridinium); a widely used herbicid. Responsible for the secretion of cationic drugs across the brush border membranes.
- Gene Name:
- SLC47A1
- Uniprot ID:
- Q96FL8
- Molecular Weight:
- 61921.585 Da
References
- Wittwer MB, Zur AA, Khuri N, Kido Y, Kosaka A, Zhang X, Morrissey KM, Sali A, Huang Y, Giacomini KM: Discovery of potent, selective multidrug and toxin extrusion transporter 1 (MATE1, SLC47A1) inhibitors through prescription drug profiling and computational modeling. J Med Chem. 2013 Feb 14;56(3):781-95. doi: 10.1021/jm301302s. Epub 2013 Jan 22. [23241029 ]
- General Function:
- Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
- Specific Function:
- Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are retained intracellularly and undergo ubiquitin-dependent degradation.
- Gene Name:
- KCNH2
- Uniprot ID:
- Q12809
- Molecular Weight:
- 126653.52 Da
References
- Keseru GM: Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods. Bioorg Med Chem Lett. 2003 Aug 18;13(16):2773-5. [12873512 ]