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HCID 149096Erstellt: 27. Oktober 2026

Levofloxacin

Levofloxacin · LEVOFLOXACIN HCL · Ophthalmic · 7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (S)- · levoflaxacin · Cravit · Levaquin · L-Ofloxacin

https://huagongshe.com/de/chemical/149096

Molekülstruktur von Levofloxacin

Identifikatoren & physikalische Daten

CAS No.100986-85-4
SummenformelC18H20FN3O4
Durchschnittliche Molmasse361,4 g/mol
Monoisotopische Masse361,14378434 g/mol
SMILESC[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23
InChIKeyGSDSWSVVBLHKDQ-JTQLQIEISA-N
PubChem CID149096
ChEMBLCHEMBL33
ChEBICHEBI:63598
EC No.600-146-0
DTXSIDDTXSID0041060

Chemische & physikalische Eigenschaften

XLogP-0,4
Polarare Oberfläche (TPSA)73,3
H-Brücken-Donoren1
H-Brücken-Akzeptoren8
Frei drehbare Bindungen2
Schwere Atome26
Formalladung0
Komplexität634
ArzneimittelPharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic usePharmaceuticals -> AntibioticsPharmaceuticals -> Used in Switzerland
LogP (Verteilungskoeffizient)log Kow = -0.39
Color/FormLight yellowish -white to yellow-white crystal or crystalline powderNeedles from ethanol + ethyl ether
LöslichkeitSparingly solubleFreely soluble in glacial acetic acid, chloroformsparingly soluble in water>54.2 [ug/mL] (The mean of the results at pH 7.4)chloroform: soluble10mg/mLSlightly soluble in water or methanol. Soluble in glacial acetic acid or dichloromethane
Human DrugsBreast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsQuinolonesFluoroquinolonesFDA approved drugs -> Active ingredientEMA approved medicines: Human medicinePharmaceuticalsAntituberculosis medicines
DecompositionWhen heated to decomposition material emits toxic fumes of /nitrogen oxides and hydrogen fluoride/.
Schmelzpunkt225-227C225-227 °C (decomposes)218°C
Optical RotationSpecific optical rotation: -76.9 deg at 23 °C/D ( c = 0.385 in 05N NaOH)
Physical DescriptionSolid
Dissociation Constants8.126.18.66.25pKa1 = 6.24 (carboxylic acid moiety)
Collision Cross Section188.5 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]191.4 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]176.98 Ų [M+H-H2O]+ [CCS Type: TW
Other Experimental PropertiesThe molecule exists as a zwitterion at the pH conditions in the small intestine.
Siedepunkt572℃
Dichte1.48±0.1 g/cm3(Predicted)
Flammpunkt>110°(230°F)
LagerbedingungenKeep in dark place,Sealed in dry,2-8°C
pKa (Säurekonstante)5.19±0.40(Predicted)
Aggregatzustandpowder
Farbewhite to faint yellow
Biologische Quellesynthetic
Merck14,6771
BRN7327015
BCS Class3,1
InChIKeyGSDSWSVVBLHKDQ-JTQLQIEISA-N
SMILESO=C1C2=CC(F)=C(C3=C2N([C@H](CO3)C)C=C1C(O)=O)N4CCN(C)CC4.[xHCl]
CAS Datenbank100986-85-4(CAS DataBase Reference)
EPA chemische Informationen7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (3S)- (100986-85-4)

Sicherheit & Vorschriften

GHS-EinstufungDangerH302 (98.3%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P233, P260, P261, P263, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P318, P321, P330, P333+P317, P342+P316, P362+P364, P403, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 174 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
BrandpotenzialThis material is assumed to be combustible.
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including levofloxacin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Toxic Combustion ProductsEmits toxic fumes under fire conditions.
Hazard Classes and CategoriesAcute Tox. 4 (98.3%)
BrandbekämpfungsverfahrenWater spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.
LagerbedingungenStore in tight, light-resistant container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.
ReinigungsverfahrenWear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labelled container for disposal. Wash spill site.
EntsorgungsverfahrenSRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Anwendungen & Verwendung

Beschreibung

Levofloxacin, the optically active S-isomer of the fluoroquinolone antibiotic ofloxacin, is two to four times more potent than ofloxacin with reportedly less side effects in treating infections of the lower respiratory and urinary tract, prostate infections and sexually transmitted diseases. It has broad and potent antibacterial activity over common Grampositive and -negative aerobic pathogens and obligate anaerobes. Different from the cephem antibiotics, levofloxacin is unique in its marked selectivity against members of the family Enterobacteriaceae and its negligible effect on predominant anaerobes. Levofloxacin also exhibits satisfactory antimicrobial effects in surgical infections and it may be used for treatment of gastrointestinal infections such as traveler’s diarrhea associated with the pathogenic Enterobacteriaceae.

Verwenden

Antibacterial.

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Preventive MeasuresEngineering controls such as exhaust ventilation are recommended.As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Personal Protective Equipment (PPE)Respiratory Protection: Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used. Gloves: Chemically compatible. Eye Protection: Safety glasses or goggles. Protective Clothing: Protect exposed skin.
TreatmentIn the event of an acute overdosage, the stomach should be emptied. The patient should be observed and appropriate hydration maintained. Levofloxacin is not efficiently removed by hemodialysis or peritoneal dialysis. (L1009)
WechselwirkungenWarfarin: Potential pharmacologic interaction (increased prothrombin time). Monitor prothrombin time or other suitable coagulation tests and monitor for bleeding.Theophylline: Pharmacokinetic interaction unlikely. However, pharmacokinetic interaction (increased theophylline half-life and increased risk of theophylline-related adverse effects) occurs with some other quinolones. Closely monitor serum theophylline concentrations and adjust theophylline dosage accordinglyconsider that adverse theophylline effects (e.g., seizures) may occur with or without elevated theophylline concentrations.Sucralfate: Potential pharmacokinetic interaction (decreased levofloxacin absorption)no pharmacokinetic interaction if given 2 hours apart. Administer levofloxacin at least 2 hours before or 2 hours after sucralfate.Probenecid: Potential pharmacokinetic interaction (increased levofloxacin AUC and half-life). Not considered clinically importantdosage adjustments are not required.For more Interactions (Complete) data for Levofloxacin (16 total), please visit the HSDB record page.
Gesundheitliche AuswirkungenIrreversible peripheral neuropathy, central nervous system toxicity, cardiovascular toxicity, tendon / articular toxicity, and hepatic toxicity. Toxic epidermal necrolysis, coagulation abnormalities and pancytopenia are other possible adverse effect of levofloxacin. Administration of commercial levofloxin (Levaquin), increased risk of tendinitis and tendon rupture in all ages. This adverse reaction most frequently involves the Achilles tendon (L1009, L1017).
HepatotoxicityIn short term studies, levofloxacin has been associated with minor elevations in serum ALT and AST levels in 2% to 5% of patients. The abnormalities were usually asymptomatic and transient and rarely require dose modification. With its wide scale use, levofloxacin has been implicated in in at least 50 instances of clinically apparent liver injury mostly in isolated case reports. The clinical presentation and course are typical of the hepatotoxicity of other fluoroquinolones, and the injury is likely a class effect. The latency to onset is usually short (1 to 3 weeks) and the onset is often abrupt with a hepatocellular or mixed pattern of injury, jaundice and, in some instances, hepatic failure. Cholestatic hepatitis can also occur. Immunoallergic features such as fever, rash and eosinophilia are common, but not particularly prominent. Autoantibodies are rare. The liver injury is usually self-limited, but several cases of acute liver failure have been linked to fluoroquinolones as well as instances of prolonged jaundice, cholestasis and vanishing bile duct syndrome. Levofloxacin, like ciprofloxacin, has also been implicated hypersensitivity reactions including rare cases of Stevens Johnson syndrome and toxic epidermal necrolysis, which may be accompanied by liver injury. While liver injury from levofloxacin is rare, the fluoroquinolones collectively are among the most frequent causes of clinically apparent liver injury including fatal cases and cases of chronic liver injury and bile duct paucity.
ÖkotoxizitätswerteEC50Species: Microcystis aeruginosa (Blue-Green Algae)Conditions: freshwater, static, 20 °CConcentration: 7.9 ug/L for 5 days (95% confidence interval: 6.4-9.4 ug/L)Effect: population, decreased chlorophyll A concentration /100% purity formulation/Species: Pseudokirchneriella subcapitata (Green Algae)Concentration: 7400 ug/L for 3 days (95% confidence interval: 6400-8400 ug/L)Species: Lemna minor (Duckweed)Conditions: freshwater, renewal, 20 °CConcentration: 51 ug/L for 7 days (95% confidence interval: 8.6-94 ug/L)Effect: population, decreased abundance (counted number of fronds) /100% purity formulation/
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 44,143 for the sterioisomer,ofloxacin(2) indicates that levofloxacin is expected to be immobile in soil(SRC). The pKa1 of levofloxacin is 6.24 (carboxylic acid moiety)(1) and pKa2 = 8.74 for analogous ciprofloxacin for the nitrogen on the piperazinyl ring(3)at pHs greater than 6.24, the acid will be primarily dissociated and at pHs less than approximately 8.74, the nitrogen will be primarily protonated(SRC)therefore, levofloxacin will have an ionic charge at any environmental pH(SRC). Volatilization from moist soil is not expected because the compound exists as an ion and ions do not volatilize. Levofloxacin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.8X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Using the OECD closed bottle biodegradation study, 0% degradation over a 40-day incubation period was observed for analogous ciprofloxacin(5), indicating that biodegradation may not be an important environmental fate process for levofloxacin in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), a Koc value of 44,143(2) indicates that levofloxacin is expected to adsorb to suspended solids and sediment(SRC). The pKa1 of levofloxacin is 6.24 (carboxylic acid moiety)(1) and pKa2 = 8.74 for analogous ciprofloxacin for the nitrogen on the piperazinyl ring(3)therefore, levofloxacin will have an ionic charge at any environmental pH(SRC). Due to this ionic state, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from a log Kow of -0.39 for sterioisomer ofloxacin(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Using the OECD closed bottle biodegradation study, 0% degradation over a 40-day incubation period was observed for analogous ciprofloxacin(7), indicating that biodegradation may not be an important environmental fate process for levofloxacin in water(SRC).AQUATIC FATE: Using outdoor aquatic field microcosms, levofloxacin, at concentrations of 1.00, 10.00, 100.00, and 300.00 ug/L exhibited half-lives of 6.2, 6.5, 6.0, and 6.3 days, overall mean of 6.3 days, with photodegradation being the main loss process. Photoproducts have been identified as analogues altered at the N-methylpiperazine moiety and reached a maximum by 2 hours after which their concentrations decreased(1). Therefore levofloxacin may be susceptible to direct photolysis by sunlight(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), levofloxacin, which has an estimated vapor pressure of 8.8X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase levofloxacin may be removed from the air by wet or dry deposition(SRC). Levofloxacin in solution is susceptible to photodegradation in natural light, exhibiting a mean half-life of 6.3 days(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).
Unerwünschte WirkungenThe primary adverse effects of levofloxacin include nausea, photosensitivity, diarrhea, headache, tendinitis, tendon rupture, hyper-hypoglycemia, seizures, prolonged QT interval, and peripheral neuropathy. Clinicians should carefully prescribe levofloxacin to patients with a history of prolonged QT intervals. Avoid or minimize exposure to natural or artificial sunlight while taking levofloxacin to reduce the occurrence of phototoxicity. Research has determined prolonged levofloxacin is linked with a higher risk of fungal and bacterial superinfection (eg, pseudomembranous colitis).
ExpositionspfadeIngestioninjectionskin contact (L1017). 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.
ToxizitätsübersichtThe elimination half-life of levofloxacin ranges from 27 to 35 hours in adults with renal impairment, depending on severity, compared with 6 to 8 hours in healthy adults. This prolonged half-life indicates that dosing adjustment is necessary for these patients.Neurotoxicity, including non-convulsive status epilepticus, has been reported with levofloxacin. Levofloxacin has a low potential for acute toxicityhowever, the stomach needs to be emptied during an acute overdose. The patient should be under observation with adequate maintenance of hydration. Hemodialysis or peritoneal dialysis can not adequately remove levofloxacin. The role of enhancing drug elimination with forced dilution is not clear. Activated oral charcoal administration is also a recommended approach with appropriate conditions.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 resealingDNA replication and transcription is inhibited.
Ökotoxizitätsauszüge/AQUATIC SPECIES/ Toxicity tests were performed with seven fluoroquinolone antibiotics, ciprofloxacin, lomefloxacin, ofloxacin, levofloxacin, clinafloxacin, enrofloxacin, and flumequine, on five aquatic organisms. Overall toxicity values ranged from 7.9 to 23,000 ug/L. The cyanobacterium Microcystis aeruginosa was the most sensitive organism (5-day growth and reproduction, effective concentrations [EC50s] ranging from 7.9 to 1,960 ug/L and a median of 49 ug/L), followed by duckweed (Lemna minor, 7-day reproduction, EC50 values ranged from 53 to 2,470 ug/L with a median of 106 ug/L) and the green alga Pseudokirchneriella subcapitata (3-day growth and reproduction, EC50 values ranged from 1,100 to 22,700 ug/L with a median 7,400 ug/L). Results from tests with the crustacean Daphnia magna (48-hr survival) and fathead minnow (Pimephales promelas, 7-day early life stage survival and growth) showed limited toxicity with no-observed-effect concentrations at or near 10 mg/L. Fish dry weights obtained in the ciprofloxacin, levofloxacin, and ofloxacin treatments (10 mg/L) were significantly higher than in control fish. The hazard of adverse effects occurring to the tested organisms in the environment was quantified by using hazard quotients. An estimated environmental concentration of 1 ug/L was chosen based on measured environmental concentrations previously reported in surface waterat this level, only M. aeruginosa may be at risk in surface water. However, the selective toxicity of these compounds may have implications for aquatic community structure.
Signs and SymptomsSide effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face.
Soil Adsorption/MobilityUsing a centric flurisol (Germany80.1% sand16.7% silt2.5% claypH 5.3), a measured Koc of 44,143 was reported for the steroisomer, ofloxacin(1). According to a classification scheme(2), this Koc value suggests that levofloxacin is expected to be immobile in soil. The pKa1 of levofloxacin is 6.24 (carboxylic acid moiety)(1) and pKa2 = 8.74 for analogous ciprofloxacin for the nitrogen on the piperazinyl ring(3)at pHs greater than 6.24, the acid will be primarily dissociated and at pHs less than 8.74, the nitrogen will be primarily protonated(SRC)therefore, levofloxacin will have an ionic charge at any environmental pH(SRC).
Wassergefährdungsklasse (WGK)3
UN-TransportnummerUN 1648 3 / PGII
Zollcode29349990
RTECS-Nr.UU8815550
R-Sätze (R)22-42/43-68-20/21/22-64-63
ToxizitätLD50 oral in rat: 1478mg/kg
GefahrensymboleXn
Sicherheitshinweise (S)26-36/37/39-36
Gefahrstoffdaten100986-85-4(Hazardous Substances Data)