Levofloxacin: Difference between revisions

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			{{drugbox \|
	{{newinfobox}}
		⚫	\| IUPAC_name = (-)-(S)-9-fluoro-2,3-dihydro-3-methyl-10-<br>(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido<br>-1,4-benzoxazine-6-carboxylic acid
	{{infoboxneeded\|Drugbox}}
			\| image = {{PAGENAME}}.png

			\| width = 200px
	{\| border="1" cellpadding="3" cellspacing="0" width="250px" align="right" style="border-collapse: collapse; margin: 0 0 0 0.5em"
			\| CAS_number = 100986-85-4
	\|-
			\| ATC_prefix = J01
	\| bgcolor="#ffffff" align="center" colspan="2" \|
			\| ATC_suffix = MA12
	]<br/>
			\| ATC_supplemental = {{ATC\|S01\|AX19}}
	''Levofloxacin''
			\| PubChem = 149096
	\|-
			\| DrugBank = APRD00477
⚫	\| ~~align="center"~~ ~~colspan~~=~~"2" \|~~ ''(-)-(S)-9-fluoro-2,3-dihydro-3-methyl-<BR>~~10-~~(4-methyl-1-piperazinyl)-7-oxo-~~<BR>~~7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid''
			\| chemical_formula =
	\|- align="center" style="border-bottom: 3px solid gray"
			\| C = 18 \|H = 20 \|F = 1 \|N = 3 \|O = 4
	\| ''']''' <br/> 100986-85-4
			\| molecular_weight = 361.368 ]/]
	\| ''']''' <br/> J01MA12, S01AX19
			\| bioavailability = 99%
	\|-
			\| protein_bound = 24 to 38%
	\| bgcolor="#eeeeee" \| ]
			\| metabolism = ]
	\| bgcolor="#ddeeff" \| C<sub>18</sub>H<sub>20</sub>FN<sub>3</sub>O<sub>4</sub>
			\| elimination_half-life = 6 to 8 ]s
	\|-
			\| excretion = Urinary
	\| bgcolor="#eeeeee" \| ]
			\| pregnancy_category = C (])
	\| bgcolor="#ddeeff" \| 361.371
			\| legal_status = ]
	\|-
			\| routes_of_administration = ], ]
	\| bgcolor="#eeeeee" \| ]
		⚫	}}
	\| bgcolor="#ddeeff" \| 100%
	\|-
	\| bgcolor="#eeeeee" \| Metabolism
	\| bgcolor="#ddeeff" \| slightly
	\|-
	\| bgcolor="#eeeeee" \| ]
	\| bgcolor="#ddeeff" \| 6-8 hrs
	\|-
	\| bgcolor="#eeeeee" \| ]
	\| bgcolor="#ddeeff" \| Urine (> 85%)
	\|-
	\| bgcolor="#eeeeee" \| ]
	\| bgcolor="#ddeeff" \| not to be used
	\|-
	\| bgcolor="#eeeeee" \| ]
	\| bgcolor="#ddeeff" \| ?
	\|-
	\| bgcolor="#eeeeee" \| Routes of administration
	\| bgcolor="#ddeeff" \| oral and iv
	\|-
⚫	\|}

	'''Levofloxacin''' is a ] ], marketed by ] under the trade name '''Levaquin'''. Chemically, levofloxacin is the S-] (L-]) of ].		'''Levofloxacin''' is a ] ], marketed by ] under the trade name '''Levaquin'''. Chemically, levofloxacin is the S-] (L-]) of ].

Revision as of 21:32, 14 June 2006

Pharmaceutical compound

Levofloxacin
Clinical data

Pregnancy category	C (United States)
Routes of administration	Oral, IV
ATC code	J01MA12 (WHO) S01AX19 (WHO)
Legal status
Legal status	US: WARNING Prescription Only
Pharmacokinetic data
Bioavailability	99%
Protein binding	24 to 38%
Metabolism	Renal
Elimination half-life	6 to 8 hours
Excretion	Urinary
Identifiers
IUPAC name (-)-(S)-9-fluoro-2,3-dihydro-3-methyl-10- (4-methyl-1-piperazinyl)-7-oxo-7H-pyrido -1,4-benzoxazine-6-carboxylic acid
CAS Number	100986-85-4
PubChem CID	149096
DrugBank	APRD00477
CompTox Dashboard (EPA)	DTXSID0041060
ECHA InfoCard	100.115.581
Chemical and physical data
Formula	C₁₈H₂₀FN₃O₄
Molar mass	361.368 g/mol g·mol

Levofloxacin is a fluoroquinolone antibiotic, marketed by Ortho-McNeil under the trade name Levaquin. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin.

Levofloxacin is effective against a number of gram-positive and gram-negative bacteria. Because of its broad spectrum of action, levofloxacin is frequently prescribed empirically for a wide range of infections (e.g. pneumonia, urinary tract infection) before the specific causal organism is known. If the causal organism is identified, levofloxacin may be discontinued and the patient may be switched to an antibiotic with a narrower spectrum of activity.

Gram-positive bacteria

Enterococcus faecalis (many strains are only moderately susceptible)
Staphylococcus aureus (methicillin-susceptible strains)
Staphylococcus epidermidis (methicillin-susceptible strains)
Staphylococcus saprophyticus
Streptococcus pneumoniae (including penicillin-resistant strains*)
Streptococcus pyogenes

Levofloxacin only has moderate Gram-positive coverage; beta-lactams (e.g. ceftriaxone) or glycopeptides (e.g. vancomycin) are generally preferred for this indication.

Gram-negative bacteria

Other

Some information extracted from Levaquin Prescribing information.

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine (Sulfamethazine, Sulfadimerazine, Sulfadimezine) Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin Ofloxacin Enoxacin Fleroxacin Lomefloxacin Nadifloxacin/Levonadifloxacin/Alalevonadifloxacin Norfloxacin Pefloxacin Rufloxacin
3rd generation	Levofloxacin Balofloxacin Grepafloxacin Pazufloxacin Sparfloxacin Temafloxacin Tosufloxacin
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin Garenoxacin Prulifloxacin Sitafloxacin Trovafloxacin/Alatrofloxacin
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Secnidazole

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin Rifabutin Rifapentine Rifaximin Rifalazil
Lipiarmycins	Fidaxomicin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

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