A synthetic fluoroquinolone (fluoroquinolones) antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.

Structure

Similar Structures

Synonyms

(-)-Ofloxacin
(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
(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
(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
(S)-Ofloxacin
L-Ofloxacin
Levofloxacin
Levofloxacin anhydrous
Levofloxacine
Levofloxacino
Levofloxacinum
Ofloxacin S-(-)-form

External IDs

MP-376

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Levofloxacin hemihydrate	6GNT3Y5LMF	138199-71-0	SUIQUYDRLGGZOL-RCWTXCDDSA-N

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Act Levofloxacin	Tablet	250 mg	Oral	Teva	2009-06-24	Not applicable
Act Levofloxacin	Tablet	750 mg	Oral	Teva	2009-06-24	Not applicable
Act Levofloxacin	Tablet	500 mg	Oral	Teva	2009-06-24	Not applicable
Iquix	Solution	15 mg/1mL	Ophthalmic	Vistakon Pharmaceuticals	2004-06-01	2017-04-13
Levaquin	Tablet, film coated	500 mg/1	Oral	Physicians Total Care, Inc.	2000-05-11	Not applicable
Levaquin	Injection, solution	5 mg/1mL	Intravenous	Ortho-McNeil-Janssen Pharmaceuticals Inc.	1996-12-20	2009-07-27
Levaquin	Tablet, film coated	750 mg/1	Oral	Janssen Pharmaceuticals, Inc.	1996-12-20	2020-05-31
Levaquin	Tablet, film coated	500 mg/1	Oral	Rebel Distributors	1996-12-20	Not applicable
Levaquin	Tablet, film coated	250 mg/1	Oral	McNeil Pharmaceuticals	1996-12-20	2012-02-29
Levaquin	Injection, solution, concentrate	25 mg/1mL	Intravenous	McNeil Pharmaceuticals	1996-12-20	2010-09-30

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-levofloxacin	Tablet	250 mg	Oral	Apotex Corporation	2009-06-24	Not applicable
Apo-levofloxacin	Tablet	750 mg	Oral	Apotex Corporation	2009-06-24	Not applicable
Apo-levofloxacin	Tablet	500 mg	Oral	Apotex Corporation	2009-06-24	Not applicable
Auro-levofloxacin	Tablet	500 mg	Oral	Auro Pharma Inc	2016-04-12	Not applicable
Auro-levofloxacin	Tablet	250 mg	Oral	Auro Pharma Inc	2016-04-12	Not applicable
Auro-levofloxacin	Tablet	750 mg	Oral	Auro Pharma Inc	2016-04-12	Not applicable
Ava-levofloxacin	Tablet	500 mg	Oral	Avanstra Inc	2011-09-15	2014-08-21
Ava-levofloxacin	Tablet	250 mg	Oral	Avanstra Inc	2011-09-15	2014-08-21
Dom-levofloxacin	Tablet	250 mg	Oral	Dominion Pharmacal	Not applicable	Not applicable
Dom-levofloxacin	Tablet	750 mg	Oral	Dominion Pharmacal	Not applicable	Not applicable

International/Other Brands

Cravit / Elequine / Floxel / Leroxacin / Levokacin / Levox / Levoxacin / Mosardal / Nofaxin / Reskuin / Tavanic

Categories

UNII

RIX4E89Y14

CAS number

100986-85-4

Weight

Average: 361.3675
Monoisotopic: 361.143784348

Chemical Formula

C₁₈H₂₀FN₃O₄

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

IUPAC Name

(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0⁵,¹³]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

SMILES

C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1

Pharmacology

Indication

For the treatment of bacterial conjunctivitis caused by susceptible strains of the following organisms: Corynebacterium species, Staphylococus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus (Groups C/F/G), Viridans group streptococci, Acinetobacter lwoffii, Haemophilus influenzae, Serratia marcescens.

Associated Conditions

Pharmacodynamics

Levofloxacin, a fluoroquinolone antiinfective, is the optically active L-isomer of ofloxacin. Levofloxacin is used to treat bacterial conjunctivitis, sinusitis, chronic bronchitis, community-acquired pneumonia and pneumonia caused by penicillin-resistant strains of Streptococcus pneumoniae, skin and skin structure infections, complicated urinary tract infections and acute pyelonephritis.

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.

Target	Actions	Organism
ADNA topoisomerase 4 subunit A	inhibitor	Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA gyrase subunit A	inhibitor	Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 2-alpha	inhibitor	Humans

Absorption

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.

Volume of distribution

Not Available

Protein binding

24-38% (to plasma proteins)

Metabolism

Mainly excreted as unchanged drug (87%); undergoes limited metabolism in humans.

Route of elimination

Mainly excreted as unchanged drug in the urine.

Half life

6-8 hours

Clearance

Not Available

Toxicity

Side effects include disorientation, dizziness, drowsiness, hot and cold flashes, nausea, slurring of speech, swelling and numbness in the face

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	The therapeutic efficacy of (R)-warfarin can be increased when used in combination with Levofloxacin.
(S)-Warfarin	The therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Levofloxacin.
2,4-thiazolidinedione	The therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Levofloxacin.
3-isobutyl-1-methyl-7H-xanthine	The metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Levofloxacin.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Levofloxacin.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Levofloxacin.
5-androstenedione	The metabolism of 5-androstenedione can be decreased when combined with Levofloxacin.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be decreased when combined with Levofloxacin.
7-Deazaguanine	The metabolism of 7-Deazaguanine can be decreased when combined with Levofloxacin.
7-ethyl-10-hydroxycamptothecin	The metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Levofloxacin.

Food Interactions

Take without regard to meals. Take with water, drink lliberally. Taking this product with orange juice can result in reduced quinolone plasma levels.

References

Synthesis Reference

Valerie Niddam-Hildesheim, "Preparation of levofloxacin and forms thereof." U.S. Patent US20030130507, issued July 10, 2003.

US20030130507

General References

Not Available

External Links

Human Metabolome Database: HMDB0001929
KEGG Drug: D08120
KEGG Compound: C07660
PubChem Compound: 149096
PubChem Substance: 46505134
ChemSpider: 131410
BindingDB: 50366826
ChEBI: 63598
ChEMBL: CHEMBL33
Therapeutic Targets Database: DAP000160
PharmGKB: PA450214
HET: LFX
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Levofloxacin

ATC Codes

J01MA12 — Levofloxacin

A02BD10 — Lansoprazole, amoxicillin and levofloxacin

J01RA05 — Levofloxacin and ornidazole

S01AE05 — Levofloxacin

AHFS Codes

08:12.18 — Quinolones

PDB Entries

3k9f / 3rae / 4juo / 4z2d / 5btg / 5bti / 5eix

FDA label

Download (139 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Recruiting	Prevention	Complications of Surgical Procedures	1
0	Recruiting	Treatment	Osteomyelitis	1
1	Completed	Diagnostic	Lung Function / Sarcoidosis, Pulmonary	1
1	Completed	Health Services Research	Healthy Volunteers	1
1	Completed	Prevention	Chronic Obstructive Pulmonary Disease (COPD)	1
1	Completed	Treatment	Cystic Fibrosis (CF)	2
1	Completed	Treatment	Healthy Volunteers	2
1	Completed	Treatment	Healthy Volunteers / The Focus of This Study Was to Assess the Effect of Food Following a Single Oral Dose of Levofloxacin Solution	1
1	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
1	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
1	Completed	Treatment	Kidney Diseases	1
1	Recruiting	Treatment	Conjunctivitis / Conjunctivitis, Bacterial	1
1	Terminated	Not Available	Infection Due to Escherichia Coli	1
1	Terminated	Treatment	Urinary Bladder, Overactive	1
1, 2	Completed	Treatment	Multi-Drug Resistant Tuberculosis / Tuberculosis Infection	1
1, 2	Recruiting	Treatment	Tuberculous Meningitis	1
1, 2	Unknown Status	Treatment	Corneal Diseases / Hypermetropia / Myopia / Pterygium	1
2	Active Not Recruiting	Treatment	Tuberculosis, Multidrug Resistant	1
2	Completed	Not Available	Healthy Volunteers	1
2	Completed	Treatment	Acute Pyelonephritis / Complicated Urinary Tract Infections	1
2	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
2	Completed	Treatment	Community Acquired Pneumonia (CAP)	1
2	Completed	Treatment	Community-Acquired Bacterial Pneumonia (CABP)	1
2	Completed	Treatment	Cystic Fibrosis (CF)	1
2	Completed	Treatment	Diabetic Foot Ulcers (DFU)	3
2	Not Yet Recruiting	Treatment	Appendicitis Acute	1
2	Recruiting	Other	Cataracts	1
2	Recruiting	Prevention	Prophylaxis / Stem Cell Transplant Complications	1
2	Recruiting	Treatment	Acute Pyelonephritis	1
2	Recruiting	Treatment	Chronic Bacterial Prostatitis	1
2	Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	2
2	Recruiting	Treatment	Sarcoidosis; Antimycobacterial Therapy	1
2	Recruiting	Treatment	Tuberculosis, Multidrug Resistant	1
2	Suspended	Supportive Care	Stem Cell Transplant Complications	1
2	Terminated	Treatment	Community Acquired Pneumonia (CAP)	1
2	Terminated	Treatment	Infected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee	1
2	Terminated	Treatment	Malignancies / Non-Hodgkin's Lymphoma (NHL)	1
2, 3	Completed	Treatment	Acute Exacerbation of Chronic Obstructive Pulmonary Disease	1
2, 3	Completed	Treatment	Bronchitis / Chronic Bronchitis	1
2, 3	Completed	Treatment	Cellulitis / Skin Diseases, Infectious	1
2, 3	Completed	Treatment	Pneumonia	1
2, 3	Recruiting	Treatment	Extensively Drug Resistant Tuberculosis / Tuberculosis Infection / Tuberculosis, Multidrug Resistant	1
2, 3	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
2, 3	Unknown Status	Prevention	Allogeneic Stem Cell Transplantation / Malignancies	1
3	Completed	Not Available	Prostatic Hyperplasia / Prostatitis	1
3	Completed	Prevention	Cataract operation	1
3	Completed	Supportive Care	Acute Leukemias of Ambiguous Lineage / Bacterial Infections / Infections, Fungal / Musculoskeletal Complications / Neutropenias / Recurrent Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Severe or persistent diarrhea / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies	1
3	Completed	Supportive Care	Brain and Central Nervous System Tumors / Cancer of the Ovary / Cancer, Breast / Extragonadal Germ Cell Tumor / Infection NOS / Lung Cancers / Malignant Lymphomas / Small Intestine Cancer / Testicular germ cell tumour / Unspecified Adult Solid Tumor, Protocol Specific	1
3	Completed	Treatment	Acute Lower Urinary Tract Infection	1
3	Completed	Treatment	Acute Pyelonephritis / Complicated Urinary Tract Infections	1
3	Completed	Treatment	Acute Pyelonephritis / Urinary Tract Infection Complicated	1
3	Completed	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	2
3	Completed	Treatment	Bacterial Infections / Bacteriuria / Urinary Tract Infections (UTIs) / Urologic Diseases	1
3	Completed	Treatment	Bacteriuria / Neurogenic Bladder Dysfunction / Pyelonephritis / Urinary Tract Infections (UTIs) / Urologic Diseases	1
3	Completed	Treatment	Chronic Bronchitis	2
3	Completed	Treatment	Community Acquired Pneumonia (CAP)	1
3	Completed	Treatment	Community-Acquired Infections / Cross Infection / Pneumonia, Bacterial	1
3	Completed	Treatment	Complicated Urinary Tract Infections	1
3	Completed	Treatment	Complicated Urinary Tract Infections (cUTIs) / CUTI	1
3	Completed	Treatment	Complicated Urinary Tract Infections / Pyelonephritis	1
3	Completed	Treatment	Cystic Fibrosis (CF)	2
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
3	Completed	Treatment	Maxillary Sinusitis	2
3	Completed	Treatment	Maxillary Sinusitis / Sinusitis	1
3	Completed	Treatment	Otitis Media (OM)	2
3	Completed	Treatment	Pelvic Inflammatory Disease (PID)	1
3	Completed	Treatment	Pneumonia	6
3	Completed	Treatment	Pneumonia, Bacterial	1
3	Completed	Treatment	Prostatitis	3
3	Completed	Treatment	Pyelonephritis / Urinary Tract Infections (UTIs)	1
3	Completed	Treatment	Sinusitis	1
3	Completed	Treatment	Skin Diseases, Bacterial	1
3	Completed	Treatment	Skin Diseases, Infectious	1
3	Completed	Treatment	Hospital-acquired bacterial pneumonia	1
3	Not Yet Recruiting	Treatment	Chronic Rhinosinusitis (Diagnosis)	1
3	Not Yet Recruiting	Treatment	Tuberculosis, Multidrug Resistant	1
3	Recruiting	Prevention	Chronic Systolic Heart Failure / Complete atrioventricular heart block / Sick Sinus Syndrome / Syncope	1
3	Recruiting	Prevention	Leukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndromes	1
3	Recruiting	Prevention	Prevention	1
3	Recruiting	Supportive Care	Chronic Rhinosinusitis / Chronic Sinusitis - Ethmoidal Anterior / Chronic Sinusitis - Ethmoidal, Posterior / Chronic Sinusitis - Frontoethmoidal / Chronic Sinusitis, Ethmoidal / Chronic Sinusitis, Sphenoidal / Nasal Polyp - Posterior / Polyps, Nasal	1
3	Recruiting	Treatment	Chronic Rhinosinusitis	1
3	Recruiting	Treatment	Helicobacter-associated Gastritis	1
3	Recruiting	Treatment	Indigestion	1
3	Recruiting	Treatment	Infective Endocarditis	1
3	Recruiting	Treatment	Keratitis; Infectious Disease (Manifestation)	1
3	Recruiting	Treatment	Multi-Drug Resistant Tuberculosis	1
3	Recruiting	Treatment	Tuberculosis, Multidrug Resistant	1
3	Terminated	Treatment	Infection NOS	1
3	Terminated	Treatment	Infection in Solid Organ Transplant Recipients / Latent Tuberculosis Infection (LTI)	1
3	Terminated	Treatment	Staphylococcus	1
3	Terminated	Treatment	Tuberculosis Infection	1
3	Unknown Status	Supportive Care	Fever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / Neutropenias / Unspecified Adult Solid Tumor, Protocol Specific	1
3	Unknown Status	Treatment	Acute Exacerbation of Chronic Bronchitis (AECB)	1
3	Withdrawn	Treatment	Tuberculosis Multi Drug Resistant Active	1
4	Active Not Recruiting	Treatment	Helicobacter Pylori Gastrointestinal Tract Infection	1
4	Completed	Not Available	Bacteremia / Endocarditis / Sepsis / Staphylococcus Aureus	1
4	Completed	Not Available	Helicobacter Infections	1
4	Completed	Basic Science	Cataracts	1
4	Completed	Basic Science	Healthy Volunteers	1
4	Completed	Prevention	Disease Due to BK Polyomavirus / Kidney Transplant Infection	1
4	Completed	Treatment	Acute Bacterial Sinusitis (ABS)	1
4	Completed	Treatment	Acute Exacerbation of Chronic Obstructive Pulmonary Disease	2
4	Completed	Treatment	BK Viremia	1
4	Completed	Treatment	BMI >30 kg/m2 / Critical Illness	1
4	Completed	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	3
4	Completed	Treatment	Cataract Extraction	1
4	Completed	Treatment	Cataracts	1
4	Completed	Treatment	Cataracts / Dry Eye Syndromes	1
4	Completed	Treatment	Community Acquired Pneumonia (CAP)	1
4	Completed	Treatment	Community Acquired Pneumonia (CAP) / Intensive Care Unit Syndrome	1
4	Completed	Treatment	Community-acquired / Pneumonia, Bacterial	1
4	Completed	Treatment	Cure Rate of Helicobacter Pylori Infection	1
4	Completed	Treatment	Fevers / Urinary Tract Infections (UTIs)	1
4	Completed	Treatment	Functional Dyspepsia / Peptic Ulcers	1
4	Completed	Treatment	Helicobacter Infections	1
4	Completed	Treatment	Pneumonia	1
4	Completed	Treatment	Pulmonary Tuberculosis (TB)	1
4	Not Yet Recruiting	Treatment	Antimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Not Yet Recruiting	Treatment	Antimicrobial Susceptibility Testing / Triple Therapy	1
4	Not Yet Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	3
4	Not Yet Recruiting	Treatment	Urinary Tract Infection Lower Acute	1
4	Recruiting	Prevention	Prostate Cancer	1
4	Recruiting	Treatment	Antimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Recruiting	Treatment	Bacillus Calmette-Guerin (BCG) Cystitis / Intra-vesical Instillation / Non-Muscle-invasive Bladder Cancer (NMIBC)	1
4	Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	2
4	Recruiting	Treatment	Cholangitis	1
4	Recruiting	Treatment	Community Acquired Pneumonia (CAP)	1
4	Recruiting	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
4	Recruiting	Treatment	Mycoplasma Pneumoniae Pneumonia	1
4	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
4	Recruiting	Treatment	Urinary Tract Infections (UTIs)	2
4	Terminated	Basic Science	Transplantation, Corneal	1
4	Terminated	Treatment	Acute Uncomplicated Pyelonephritis	1
4	Terminated	Treatment	Appendicitis	1
4	Terminated	Treatment	Complicated Urinary Infection	1
4	Terminated	Treatment	Pneumonia, Pneumococcal	1
4	Unknown Status	Treatment	Community Acquired Pneumonia (CAP)	1
4	Unknown Status	Treatment	Eradication Rate for Helicobacter	1
4	Unknown Status	Treatment	Urinary Tract Infections (UTIs)	1
4	Withdrawn	Treatment	Helicobacter Pylori Gastrointestinal Tract Infection	1
Not Available	Active Not Recruiting	Other	Anti-Bacterial Agents / Microbiota	1
Not Available	Completed	Not Available	Acute maxillary sinusitis caused by M. catarrhalis	1
Not Available	Completed	Not Available	End Stage Renal Disease (ESRD) / Infection NOS	1
Not Available	Completed	Prevention	Endophthalmitis	1
Not Available	Completed	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	3
Not Available	Completed	Treatment	Chronic Endometritis	1
Not Available	Completed	Treatment	Gastritis	1
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
Not Available	Completed	Treatment	Osteoarticular Infections	1
Not Available	Enrolling by Invitation	Treatment	Appendicitis Acute	1
Not Available	Not Yet Recruiting	Treatment	Antibiotics / Infection NOS / Percutaneous Nephrolithotomy / Sepsis	1
Not Available	Recruiting	Not Available	Tuberculosis Infection	1
Not Available	Recruiting	Treatment	Appendicitis Acute	1
Not Available	Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	2
Not Available	Recruiting	Treatment	Bronchiectasis	1
Not Available	Recruiting	Treatment	Prosthetic Joint Infection	1
Not Available	Terminated	Treatment	Acute Watery Diarrhea / Dysentery/Febrile Diarrhea	1
Not Available	Unknown Status	Not Available	Asymptomatic Infections / Bacteriuria / Transplantation Infection / Urinary Tract Infections (UTIs)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Advanced Pharmaceutical Services Inc.
Apotheca Inc.
A-S Medication Solutions LLC
Atlantic Biologicals Corporation
Cardinal Health
Comprehensive Consultant Services Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
H.J. Harkins Co. Inc.
Hospira Inc.
Innoviant Pharmacy Inc.
Janssen-Ortho Inc.
Lake Erie Medical and Surgical Supply
Letco Medical Inc.
Liberty Pharmaceuticals
McNeil Laboratories
Medisca Inc.
Murfreesboro Pharmaceutical Nursing Supply
Neuman Distributors Inc.
Nucare Pharmaceuticals Inc.
OMJ Pharmaceuticals
Ortho Mcneil Janssen Pharmaceutical Inc.
Ortho-McNeil-Janssen Pharmaceuticals Inc.
PD-Rx Pharmaceuticals Inc.
Physicians Total Care Inc.
Prepackage Specialists
Rebel Distributors Corp.
Redpharm Drug
Remedy Repack
Santen Inc.
Southwood Pharmaceuticals
Stat Rx Usa
Teva Pharmaceutical Industries Ltd.
Vistakon Pharmaceuticals LLC
Yuhan Chemical Industrial Co. Ltd.

Dosage forms

Form	Route	Strength
Solution	Ophthalmic	15 mg/1mL
Injection, solution	Intravenous	5 mg/1mL
Injection, solution, concentrate	Intravenous	25 mg/1mL
Solution	Oral	25 mg/1mL
Tablet, film coated	Oral	250 mg/1
Tablet, film coated	Oral	500 mg/1
Tablet, film coated	Oral	750 mg/1
Solution	Intravenous	25 mg
Solution	Intravenous	5 mg
Injection	Intravenous	25 mg/1mL
Injection	Intravenous	5 mg/1mL
Injection, solution	Intravenous	25 mg/1mL
Injection, solution	Intravenous	250 mg/50mL
Injection, solution	Intravenous	500 mg/100mL
Injection, solution	Intravenous	750 mg/200mL
Injection, solution	Intravenous	750 mg/150mL
Injection, solution, concentrate	Intravenous	500 mg/20mL
Injection, solution, concentrate	Intravenous	750 mg/30mL
Solution / drops	Ophthalmic	15 mg/1mL
Solution / drops	Ophthalmic	5 mg/1mL
Solution / drops	Topical	5 mg/1mL
Tablet	Oral	250 mg/1
Tablet	Oral	500 mg/1
Tablet	Oral	750 mg/1
Tablet	Oral	250 mg
Tablet	Oral	500 mg
Solution	Respiratory (inhalation)	240 mg
Solution	Ophthalmic	5 mg/1mL
Tablet	Oral	750 mg

Prices

Unit description	Cost	Unit
Iquix 1.5% Solution 5ml Bottle	81.68USD	bottle
Levofloxacin hemihydr 100% powder	42.69USD	g
Levaquin 750 mg tablet	28.06USD	each
Levaquin 750 mg leva-pak tablet	27.51USD	tablet
Levaquin 500 mg tablet	16.57USD	tablet
Iquix 1.5% eye drops	15.71USD	ml
Levaquin 250 mg tablet	13.71USD	tablet
Quixin 0.5% eye drops	12.21USD	ml
Quixin 0.5% Solution	11.4USD	ml
Levaquin i.v. 25 mg/ml vial	1.94USD	ml
Levaquin 500 mg/100 ml d5w	0.44USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5053407	No	1991-10-01	2010-12-20
US6806256	Yes	2004-10-19	2022-08-26

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	Insoluble	Not Available
logP	2.1	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.44 mg/mL	ALOGPS
logP	-0.02	ALOGPS
logP	0.65	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.94 m³·mol^-1	ChemAxon
Polarizability	36.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
MS/MS Spectrum - Quattro_QQQ 10V, N/A	LC-MS/MS	splash10-00gm-1315975420-b0c4e6cdef799fda69b4
MS/MS Spectrum - Quattro_QQQ 25V, N/A	LC-MS/MS	splash10-0abc-3459425420-e8a4ecd2f8aea93fa660
MS/MS Spectrum - Quattro_QQQ 40V, N/A	LC-MS/MS	splash10-0h9p-3513893500-1d5c8069419fa2c37ebb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-03di-0009000000-63138044688fa3ab0792
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-02t9-0019000000-265eec70cbb77077fbfa
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-03di-1290000000-3ff2c315dfac97ded8c5
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0axr-1980000000-e31472e2487627c51cea
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0adl-1930000000-3cd445f16118ecf3f610
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-0049000000-3cbab894a4b0d1165e7d
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-2492000000-62b30ac9148b06791816
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Taxonomy

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.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Quinolines and derivatives
Sub Class: Quinoline carboxylic acids
Direct Parent: Quinoline carboxylic acids
Alternative Parents: Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Benzoxazines / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / N-methylpiperazines
show 15 more
Substituents: Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Benzoxazine / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives
show 34 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: quinolone antibiotic, fluoroquinolone antibiotic, ofloxacin (CHEBI:63598)

Targets

Details1. DNA topoisomerase 4 subunit A

Kind: Protein
Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function: Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name: parC
Uniprot ID: P43702
Uniprot Name: DNA topoisomerase 4 subunit A
Molecular Weight: 83366.24 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Zheng X, Johnson C, Lu Y, Yanagihara R, Hollingshead S, Crain M, Benjamin W Jr, Waites KB: Clinical isolates of Streptococcus pneumoniae resistant to levofloxacin contain mutations in both gyrA and parC genes. Int J Antimicrob Agents. 2001 Oct;18(4):373-8. [PubMed:11691571]
Schafer J, Hovde LB, Simonson D, Rotschafer JC: In vitro pharmacodynamics of moxifloxacin versus levofloxacin against 4 strains of Streptococcus pneumoniae: 1 wild type, 2 first-step parC mutants, and 1 pump mutant. Diagn Microbiol Infect Dis. 2008 Feb;60(2):155-61. Epub 2007 Oct 29. [PubMed:17910998]
Deryke CA, Du X, Nicolau DP: Evaluation of bacterial kill when modelling the bronchopulmonary pharmacokinetic profile of moxifloxacin and levofloxacin against parC-containing isolates of Streptococcus pneumoniae. J Antimicrob Chemother. 2006 Sep;58(3):601-9. Epub 2006 Jul 19. [PubMed:16857688]

Details2. DNA gyrase subunit A

Kind: Protein
Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function: DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
Gene Name: gyrA
Uniprot ID: P43700
Uniprot Name: DNA gyrase subunit A
Molecular Weight: 97817.145 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Schmitz FJ, Hofmann B, Hansen B, Scheuring S, Luckefahr M, Klootwijk M, Verhoef J, Fluit A, Heinz HP, Kohrer K, Jones ME: Relationship between ciprofloxacin, ofloxacin, levofloxacin, sparfloxacin and moxifloxacin (BAY 12-8039) MICs and mutations in grlA, grlB, gyrA and gyrB in 116 unrelated clinical isolates of Staphylococcus aureus. J Antimicrob Chemother. 1998 Apr;41(4):481-4. [PubMed:9598779]
Brisse S, Milatovic D, Fluit AC, Verhoef J, Martin N, Scheuring S, Kohrer K, Schmitz FJ: Comparative in vitro activities of ciprofloxacin, clinafloxacin, gatifloxacin, levofloxacin, moxifloxacin, and trovafloxacin against Klebsiella pneumoniae, Klebsiella oxytoca, Enterobacter cloacae, and Enterobacter aerogenes clinical isolates with alterations in GyrA and ParC proteins. Antimicrob Agents Chemother. 1999 Aug;43(8):2051-5. [PubMed:10428935]
Messina C, Cafiso V, Campanile F, Santagati M, Stefani S: Rapid method for detection of gyrA and grlA mutations in unrelated strains of Staphylococci susceptible and resistant to levofloxacin. New Microbiol. 2001 Oct;24(4):347-53. [PubMed:11718372]

Details3. DNA topoisomerase 2-alpha

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

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 segr...
Gene Name: TOP2A
Uniprot ID: P11388
Uniprot Name: DNA topoisomerase 2-alpha
Molecular Weight: 174383.88 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Details1. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: This drug is a fluoroquinolone, and these agents are known to inhibit CYP1A2.

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Bellon A, Perez-Garcia G, Coverdale JH, Chacko RC: Seizures associated with levofloxacin: case presentation and literature review. Eur J Clin Pharmacol. 2009 Oct;65(10):959-62. doi: 10.1007/s00228-009-0717-5. Epub 2009 Aug 26. [PubMed:19707748]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Shahzadi A, Javed I, Aslam B, Muhammad F, Asi MR, Ashraf MY, Zia-ur-Rahman: Therapeutic effects of ciprofloxacin on the pharmacokinetics of carbamazepine in healthy adult male volunteers. Pak J Pharm Sci. 2011 Jan;24(1):63-8. [PubMed:21190921]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Nakamura H, Ohtsuka T, Enomoto H, Hasegawa A, Kawana H, Kuriyama T, Ohmori S, Kitada M: Effect of levofloxacin on theophylline clearance during theophylline and clarithromycin combination therapy. Ann Pharmacother. 2001 Jun;35(6):691-3. doi: 10.1345/aph.10307. [PubMed:11408986]

Transporters

Details1. Multidrug resistance protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Ito T, Yano I, Tanaka K, Inui KI: Transport of quinolone antibacterial drugs by human P-glycoprotein expressed in a kidney epithelial cell line, LLC-PK1. J Pharmacol Exp Ther. 1997 Aug;282(2):955-60. [PubMed:9262363]
Yamaguchi H, Yano I, Hashimoto Y, Inui KI: Secretory mechanisms of grepafloxacin and levofloxacin in the human intestinal cell line caco-2. J Pharmacol Exp Ther. 2000 Oct;295(1):360-6. [PubMed:10992002]
Yamaguchi H, Yano I, Saito H, Inui K: Effect of cisplatin-induced acute renal failure on bioavailability and intestinal secretion of quinolone antibacterial drugs in rats. Pharm Res. 2004 Feb;21(2):330-8. [PubMed:15032316]

Details2. Solute carrier family 22 member 6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name: SLC22A6
Uniprot ID: Q4U2R8
Uniprot Name: Solute carrier family 22 member 6
Molecular Weight: 61815.78 Da

References

Uwai Y, Okuda M, Takami K, Hashimoto Y, Inui K: Functional characterization of the rat multispecific organic anion transporter OAT1 mediating basolateral uptake of anionic drugs in the kidney. FEBS Lett. 1998 Nov 6;438(3):321-4. [PubMed:9827570]

Details3. Solute carrier family 22 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Quaternary ammonium group transmembrane transporter activity
Specific Function: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name: SLC22A2
Uniprot ID: O15244
Uniprot Name: Solute carrier family 22 member 2
Molecular Weight: 62579.99 Da

References

Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365]
Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [PubMed:10082798]

Details4. Solute carrier family 22 member 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name: SLC22A4
Uniprot ID: Q9H015
Uniprot Name: Solute carrier family 22 member 4
Molecular Weight: 62154.48 Da

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651]

Details5. Multidrug and toxin extrusion protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

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 sulfat...
Gene Name: SLC47A1
Uniprot ID: Q96FL8
Uniprot Name: Multidrug and toxin extrusion protein 1
Molecular Weight: 61921.585 Da

References

Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]
Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [PubMed:22970772]
Ohta KY, Imamura Y, Okudaira N, Atsumi R, Inoue K, Yuasa H: Functional characterization of multidrug and toxin extrusion protein 1 as a facilitative transporter for fluoroquinolones. J Pharmacol Exp Ther. 2009 Feb;328(2):628-34. doi: 10.1124/jpet.108.142257. Epub 2008 Nov 12. [PubMed:19004926]

Details6. Multidrug and toxin extrusion protein 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: Data for this transporter inhibition are limited to an in vitro study.

General Function: Drug transmembrane transporter activity
Specific Function: Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name: SLC47A2
Uniprot ID: Q86VL8
Uniprot Name: Multidrug and toxin extrusion protein 2
Molecular Weight: 65083.915 Da

References

Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]

Drug created on June 13, 2005 07:24 / Updated on April 22, 2019 17:13

Levofloxacin

Identification

Structure for Levofloxacin (DB01137)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

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Enzymes

References

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Transporters

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