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Chemistry

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Also known as: 100986-85-4, Levaquin, Quixin, (-)-ofloxacin, Cravit, Iquix
Molecular Formula
C18H20FN3O4
Molecular Weight
361.4  g/mol
InChI Key
GSDSWSVVBLHKDQ-JTQLQIEISA-N
FDA UNII
RIX4E89Y14

Levofloxacin
The L-isomer of Ofloxacin.
1 2D Structure

Levofloxacin

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 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
2.1.3 InChI Key
GSDSWSVVBLHKDQ-JTQLQIEISA-N
2.1.4 Canonical SMILES
CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
2.1.5 Isomeric SMILES
C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
RIX4E89Y14
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Anhydrous, Levofloxacin

2. Levaquin

3. Levofloxacin Anhydrous

4. Ofloxacin, (s)-isomer

5. Quixin

2.3.2 Depositor-Supplied Synonyms

1. 100986-85-4

2. Levaquin

3. Quixin

4. (-)-ofloxacin

5. Cravit

6. Iquix

7. Ofloxacin S-(-)-form

8. Tavanic

9. Levofloxacine

10. (s)-ofloxacin

11. L-ofloxacin

12. Levofloxacino

13. Levofloxacinum

14. Oftaquix

15. Floxacin

16. Levofloxacin Anhydrous

17. Dr-3355

18. Nofaxin

19. Volequin

20. Fluoroquinolone

21. Levofloxacin Hydrate

22. Mp-376

23. Levofloxacin (inn)

24. Levofloxacin (levaquin)

25. Rwj-25213

26. Levaquin (tn)

27. Elequine

28. (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

29. (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

30. Nsc-758709

31. Rix4e89y14

32. 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-, (3s)-

33. Chebi:63598

34. Quinsair

35. Mfcd00865049

36. (s)-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

37. Ofloxacin, (s)-

38. Levofloxacin [inn]

39. (s)-(-)-ofloxacin

40. (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

41. Lfx

42. Levofloxacine [inn-french]

43. Levofloxacinum [inn-latin]

44. Levofloxacino [inn-spanish]

45. Dr3355

46. Hr 355

47. Aeroquin

48. Unibiotic

49. Venaxan

50. Levofloxacin [usan:inn:jan]

51. Loxof

52. Levofloxacin (as Hemihydrate)

53. Rwj 25213-097

54. (2s)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic Acid

55. (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

56. (s)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-7h-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid

57. Smr000466387

58. Cravit (tn)

59. S-(-)-ofloxacin

60. Ccris 4074

61. (s)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2h-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic Acid

62. Levaquin In Dextrose 5% In Plastic Container

63. Unii-rix4e89y14

64. Levofiexacin

65. Ofloxcacin

66. S-ofloxacin

67. Hsdb 8028

68. Cravit Iv

69. Levofloxacin,(s)

70. Anhydrous Ofloxacin

71. Dr-3355: L-isomer Of Ofloxacin

72. (3s)-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

73. Hr-355

74. Mp 376

75. Spectrum_001719

76. Cpd000466387

77. Spectrum2_001676

78. Spectrum3_000995

79. Spectrum4_001123

80. Spectrum5_001438

81. Schembl15397

82. Bspbio_002689

83. Kbiogr_001605

84. Kbioss_002199

85. (-)-(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

86. Fluoro-methyl-(4-methylpiperazin-1-yl)-oxo-[?]carboxylic Acid

87. Mls000759524

88. Mls001165709

89. Mls001423977

90. Levofloxacin [who-dd]

91. Spectrum1504260

92. Spbio_001891

93. Dtxsid0041060

94. Gtpl10911

95. Kbio2_002199

96. Kbio2_004767

97. Kbio2_007335

98. Kbio3_001909

99. Ofloxacin S-(-)-form Hemihydrate

100. Hms1922j07

101. Hms2051g04

102. Hms2090o10

103. Hms2093e18

104. Hms2232g06

105. Pharmakon1600-01504260

106. Zinc538273

107. Ex-a1488

108. Hy-b0330

109. Levofloxacin, >=98.0% (hplc)

110. Bdbm50366826

111. Ccg-39093

112. De-108

113. Mmv687798

114. Nsc755604

115. Nsc758709

116. S1940

117. Ofloxacin S-(-)-form [mi]

118. Akos008901361

119. Akos015895104

120. Ac-7593

121. Db01137

122. Nc00094

123. Nsc 758709

124. Nsc-755604

125. Ncgc00178529-01

126. Ncgc00178529-02

127. Ncgc00178529-03

128. Ncgc00178529-06

129. 7h-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic Acid, 2,3-dihydro-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (s)-

130. As-31796

131. Lvx

132. Levofloxacin, Analytical Reference Material

133. Sbi-0206768.p001

134. L0193

135. C07660

136. D08120

137. Ab00171657-12

138. Ab00171657-13

139. Ab00171657_14

140. Ab00171657_15

141. 986l854

142. Q424193

143. Sr-05000001999

144. Levofloxacin, Antibiotic For Culture Media Use Only

145. Q-201295

146. Sr-05000001999-1

147. Brd-k09471561-001-06-7

148. Tert-butyl?2-(hydroxymethyl)pyrrolidine-1-carboxylate

149. Z1766089137

150. Levofloxacin Solution, 1.0 Mg/ml In Acetonitrile, Certified Reference Material

151. (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

152. (2s)-7-fluoro-2-methyl-6-(4-methylpiperazin-4-ium-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate

153. (s)-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

2.4 Create Date
2005-07-09
3 Chemical and Physical Properties
Molecular Weight 361.4 g/mol
Molecular Formula C18H20FN3O4
XLogP3-0.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Exact Mass361.14378429 g/mol
Monoisotopic Mass361.14378429 g/mol
Topological Polar Surface Area73.3 Ų
Heavy Atom Count26
Formal Charge0
Complexity634
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameLevaquin
PubMed HealthLevofloxacin (Injection)
Drug ClassesAntibiotic
Drug LabelLEVAQUIN is a synthetic broad-spectrum antibacterial agent for oral and intravenous administration. Chemically, levofloxacin, a chiral fluorinated carboxyquinolone, is the pure (-)-(S)-enantiomer of the racemic drug substance ofloxacin. The chemica...
Active IngredientLevofloxacin
Dosage FormTablet; Injectable; Solution
RouteInjection; Oral
Strength250mg; 250mg/10ml; 500mg; eq 500mg/20ml (eq 25mg/ml); eq 750mg/30ml (eq 25mg/ml); 750mg
Market StatusPrescription
CompanyJanssen Pharms

2 of 6  
Drug NameLevofloxacin
PubMed HealthLevofloxacin
Drug ClassesAntibiotic
Drug LabelLevofloxacin is a synthetic broad-spectrum antibacterial agent for oral and intravenous administration. Chemically, levofloxacin, a chiral fluorinated carboxyquinolone, is the pure (-)-(S)-enantiomer of the racemic drug substance ofloxacin. The chemi...
Active Ingredientsodium chloride; Levofloxacin
Dosage FormSolution/drops; Tablet; Injectable; Solution
Routeinjection; Ophthalmic; oral; Injection; Oral
Strength0.5%; 250mg; 250mg/10ml; 500mg; eq 500mg/20ml (eq 25mg/ml); eq 750mg/30ml (eq 25mg/ml); 25mg/ml; 5mg/ml; 750mg
Market StatusTentative Approval; Prescription
CompanyWockhardt; Mylan Pharma; Hospira; Teva; Apotex; Aurobindo Pharma; Torrent Pharms; Lupin; Sandoz; Cipla; Hikma Pharms; Watson Labs; Nexus Pharms; Glenmark Generics; Emcure Pharms; Hi Tech Pharma; Macleods Pharms; Claris Lifesciences; Sagent Pharms; Zydus P

3 of 6  
Drug NameQuixin
PubMed HealthLevofloxacin
Drug ClassesAntibiotic
Drug LabelQUIXIN (levofloxacin ophthalmic solution) 0.5% is a sterile topical ophthalmic solution. Levofloxacin is a fluoroquinolone antibacterial active against a broad spectrum of Gram-positive and Gram-negative ocular pathogens. Levofloxacin is the pure (...
Active IngredientLevofloxacin
Dosage FormSolution/drops
RouteOphthalmic
Strength0.5%
Market StatusPrescription
CompanySanten

4 of 6  
Drug NameLevaquin
PubMed HealthLevofloxacin (Injection)
Drug ClassesAntibiotic
Drug LabelLEVAQUIN is a synthetic broad-spectrum antibacterial agent for oral and intravenous administration. Chemically, levofloxacin, a chiral fluorinated carboxyquinolone, is the pure (-)-(S)-enantiomer of the racemic drug substance ofloxacin. The chemica...
Active IngredientLevofloxacin
Dosage FormTablet; Injectable; Solution
RouteInjection; Oral
Strength250mg; 250mg/10ml; 500mg; eq 500mg/20ml (eq 25mg/ml); eq 750mg/30ml (eq 25mg/ml); 750mg
Market StatusPrescription
CompanyJanssen Pharms

5 of 6  
Drug NameLevofloxacin
PubMed HealthLevofloxacin
Drug ClassesAntibiotic
Drug LabelLevofloxacin is a synthetic broad-spectrum antibacterial agent for oral and intravenous administration. Chemically, levofloxacin, a chiral fluorinated carboxyquinolone, is the pure (-)-(S)-enantiomer of the racemic drug substance ofloxacin. The chemi...
Active Ingredientsodium chloride; Levofloxacin
Dosage FormSolution/drops; Tablet; Injectable; Solution
Routeinjection; Ophthalmic; oral; Injection; Oral
Strength0.5%; 250mg; 250mg/10ml; 500mg; eq 500mg/20ml (eq 25mg/ml); eq 750mg/30ml (eq 25mg/ml); 25mg/ml; 5mg/ml; 750mg
Market StatusTentative Approval; Prescription
CompanyWockhardt; Mylan Pharma; Hospira; Teva; Apotex; Aurobindo Pharma; Torrent Pharms; Lupin; Sandoz; Cipla; Hikma Pharms; Watson Labs; Nexus Pharms; Glenmark Generics; Emcure Pharms; Hi Tech Pharma; Macleods Pharms; Claris Lifesciences; Sagent Pharms; Zydus P

6 of 6  
Drug NameQuixin
PubMed HealthLevofloxacin
Drug ClassesAntibiotic
Drug LabelQUIXIN (levofloxacin ophthalmic solution) 0.5% is a sterile topical ophthalmic solution. Levofloxacin is a fluoroquinolone antibacterial active against a broad spectrum of Gram-positive and Gram-negative ocular pathogens. Levofloxacin is the pure (...
Active IngredientLevofloxacin
Dosage FormSolution/drops
RouteOphthalmic
Strength0.5%
Market StatusPrescription
CompanySanten

4.2 Therapeutic Uses

Anti-Bacterial Agents; Anti-Infective Agents, Urinary; Nucleic Acid Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 2012)


Levofloxacin is used for the treatment of acute bacterial sinusitis caused by susceptible Streptococcus pneumoniae, Haemophilus influenzae, or Moraxella catarrhalis. /Included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 385


Levofloxacin is used for the treatment of community-acquired pneumonia caused by susceptible S. aureus (oxacillin-susceptible strains), S. pneumoniae (including penicillin-resistant strains (penicillin MIC of 2 ug/mL or greater)), H. influenzae, H. parainfluenzae, Klebsiella pneumoniae, Legionella pneumophila, M. catarrhalis, Chlamydophila pneumoniae (formerly Chlamydia pneumoniae), or Mycoplasma pneumoniae. /Included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 385


Levofloxacin is used for the treatment of mild to moderate complicated urinary tract infections caused by susceptible E. faecalis, Enterobacter cloacae, E. coli, K. pneumoniae, P. mirabilis, or Ps. aeruginosa and acute pyelonephritis caused by susceptible E. coli, including cases with concurrent bacteremia. /Included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 386


For more Therapeutic Uses (Complete) data for Levofloxacin (23 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ WARNING: Fluoroquinolones, including Levaquin, are associated with an increased risk of tendinitis and tendon rupture in all ages. This risk is further increased in older patients usually over 60 years of age, in patients taking corticosteroid drugs, and in patients with kidney, heart or lung transplants.

US Natl Inst Health; DailyMed. Current Medication Information for LEVAQUIN (levofloxacin) tablet, film coated for oral use; LEVAQUIN (levofloxacin) solution for oral use; LEVAQUIN (levofloxacin) injection, solution, concentrate for intravenous use; LEVAQUIN (levofloxacin) injection, solution for intravenous use (October 2011). Available from, as of March 7, 2012: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1f01e8e-97e9-11de-b91d-553856d89593


/BOXED WARNING/ WARNING: Fluoroquinolones, including Levaquin may exacerbate muscle weakness in persons with myasthenia gravis. Avoid Levaquin in patients with a known history of myasthenia gravis

US Natl Inst Health; DailyMed. Current Medication Information for LEVAQUIN (levofloxacin) tablet, film coated for oral use; LEVAQUIN (levofloxacin) solution for oral use; LEVAQUIN (levofloxacin) injection, solution, concentrate for intravenous use; LEVAQUIN (levofloxacin) injection, solution for intravenous use (October 2011). Available from, as of March 7, 2012: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1f01e8e-97e9-11de-b91d-553856d89593


Other serious and sometimes fatal events, some due to hypersensitivity, and some due to uncertain etiology, have been reported rarely in patients receiving therapy with fluoroquinolones, including Levaquin. These events may be severe and generally occur following the administration of multiple doses. Clinical manifestations may include one or more of the following: fever, rash, or severe dermatologic reactions (e.g., toxic epidermal necrolysis, Stevens-Johnson Syndrome); vasculitis; arthralgia; myalgia; serum sickness; allergic pneumonitis; interstitial nephritis; acute renal insufficiency or failure; hepatitis; jaundice; acute hepatic necrosis or failure; anemia, including hemolytic and aplastic; thrombocytopenia, including thrombotic thrombocytopenic purpura; leukopenia; agranulocytosis; pancytopenia; and/or other hematologic abnormalities. The drug should be discontinued immediately at the first appearance of skin rash, jaundice, or any other sign of hypersensitivity and supportive measures instituted.

US Natl Inst Health; DailyMed. Current Medication Information for LEVAQUIN (levofloxacin) tablet, film coated for oral use; LEVAQUIN (levofloxacin) solution for oral use; LEVAQUIN (levofloxacin) injection, solution, concentrate for intravenous use; LEVAQUIN (levofloxacin) injection, solution for intravenous use (October 2011). Available from, as of March 7, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=levofloxacin


Post-marketing reports of severe hepatotoxicity (including acute hepatitis and fatal events) have been received for patients treated with Levaquin No evidence of serious drug-associated hepatotoxicity was detected in clinical trials of over 7,000 patients. Severe hepatotoxicity generally occurred within 14 days of initiation of therapy and most cases occurred within 6 days. Most cases of severe hepatotoxicity were not associated with hypersensitivity. The majority of fatal hepatotoxicity reports occurred in patients 65 years of age or older and most were not associated with hypersensitivity. Levaquin should be discontinued immediately if the patient develops signs and symptoms of hepatitis.

US Natl Inst Health; DailyMed. Current Medication Information for LEVAQUIN (levofloxacin) tablet, film coated for oral use; LEVAQUIN (levofloxacin) solution for oral use; LEVAQUIN (levofloxacin) injection, solution, concentrate for intravenous use; LEVAQUIN (levofloxacin) injection, solution for intravenous use (October 2011). Available from, as of March 7, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=levofloxacin


For more Drug Warnings (Complete) data for Levofloxacin (19 total), please visit the HSDB record page.


4.4 Drug Indication

In oral and intravenous formulations, levofloxacin is indicated in adults for the treatment of various infections caused by susceptible bacteria, including infections of the upper respiratory tract, lower respiratory tract, skin, skin structures, urinary tract, and prostate. The oral formulation is also indicated in both adults and children 6 months of age and older for the post-exposure management of inhalational anthrax caused by _Bacillus anthracis_ and for the treatment and/or prophylaxis of plague caused by _Yersinia pestis_. In its ophthalmic formulation, levofloxacin is indicated for the treatment of bacterial conjunctivitis caused by susceptible organisms. An inhalational solution available in Canada is indicated for the management of cystic fibrosis patients aged 18 years or older with chronic pulmonary _Pseudomonas aeruginosa_ infections.


FDA Label


Quinsair is indicated for the management of chronic pulmonary infections due to Pseudomonas aeruginosa in adult patients with cystic fibrosis.

Consideration should be given to official guidance on the appropriate use of antibacterial agents.