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Also known as: 70458-92-3, Pefloxacine, Pefloxacino, Pefloxacinum, Pflx, 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Molecular Formula

C₁₇H₂₀FN₃O₃

Molecular Weight

333.36 g/mol

InChI Key

FHFYDNQZQSQIAI-UHFFFAOYSA-N

FDA UNII

2H52Z9F2Q5

A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria.

1 2D Structure

Pefloxacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)

2.1.3 InChI Key

FHFYDNQZQSQIAI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCN(CC3)C)F)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

2H52Z9F2Q5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2589 R.b.

2. Abactal

3. Dihydrate, Pefloxacin Mesylate

4. Mesylate Dihydrate, Pefloxacin

5. Mesylate, Pefloxacin

6. Peflacine

7. Pefloxacin Mesylate

8. Pefloxacin Mesylate Dihydrate

9. Pefloxacin, Silver

10. Pefloxacine

11. R.b., 2589

12. Silver Pefloxacin

2.3.2 Depositor-Supplied Synonyms

1. 70458-92-3

2. Pefloxacine

3. Pefloxacino

4. Pefloxacinum

5. Pflx

6. 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

7. Pefloxacinium

8. Eu-5306

9. 1589 Rb

10. 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic Acid

11. Eu 5306

12. Pefloxacinium Mesylate

13. Chebi:50199

14. 2h52z9f2q5

15. 3-quinolinecarboxylic Acid, 1,4-dihydro-1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-

16. 3-quinolinecarboxylic Acid,1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-

17. 1589-rb

18. Pefloxacin [inn-french]

19. Pefloxacinum [inn-latin]

20. Pefloxacino [inn-spanish]

21. Perfloxacin

22. Am-725

23. Labocton

24. Mls001049009

25. 1584rb

26. Smr000273037

27. Sr-01000356843

28. Pefloxacin (usan/inn)

29. Smr000387024

30. Einecs 274-611-8

31. Brn 0567618

32. Pefloxacin [usan:inn:ban]

33. Unii-2h52z9f2q5

34. Ccris 8210

35. Pefloxacin,(s)

36. 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-quinolinecarboxylic Acid

37. 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

38. Bas 00463355

39. Pefloxacin [mi]

40. Pefloxacin [inn]

41. Spectrum2_000034

42. Spectrum3_001971

43. Pefloxacin [usan]

44. 3-quinolinecarboxylic Acid, 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo

45. 3-quinolinecarboxylic Acid, 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-

46. Pefloxacin [who-dd]

47. Oprea1_063677

48. Oprea1_546341

49. Schembl34292

50. Bspbio_003571

51. Mls000713556

52. Mls006011797

53. Spbio_000127

54. Chembl267648

55. Cid_119525

56. Zinc1894

57. Dtxsid3048493

58. Bdbm57936

59. Kbio3_002945

60. Hms1613e05

61. Hms2090h09

62. Hms3713g04

63. Bcp20511

64. Hy-b0147

65. Bbl008795

66. Mfcd00865015

67. Stk169677

68. Akos000280245

69. Ccg-111464

70. Cs-1961

71. Db00487

72. Ncgc00177986-04

73. Vs-01991

74. Sbi-0206758.p001

75. Db-055417

76. Ft-0630798

77. Vu0243371-6

78. D02306

79. P-1198

80. Ab00600922-12

81. Ab00600922-14

82. Ab00600922_15

83. Ab00600922_16

84. 458p923

85. Pefloxacin, Antibiotic For Culture Media Use Only

86. Q2601859

87. Sr-01000356843-1

88. Sr-01000356843-6

89. Brd-k55034111-001-02-0

90. Brd-k55034111-066-02-3

91. Brd-k55034111-066-07-2

92. F5577-0091

93. 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methylpiperazinyl)quinoline-3-carboxylic Acid

94. 1-ethyl-6-fluoro-1,4-dihydro-7-(4-methyl-1- Piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

95. 1-ethyl-6-fluoro-4-keto-7-(4-methylpiperazino)quinoline-3-carboxylic Acid;mesylic Acid

96. 1-ethyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carbo

97. 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylicacid

98. 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate

99. 1-ethyl-6-fluoranyl-7-(4-methylpiperazin-1-yl)-4-oxidanylidene-quinoline-3-carboxylic Acid;methanesulfonic Acid

100. 1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid;methanesulfonic Acid

2.4 Create Date

2005-07-07

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₀FN₃O₃
Molecular Weight	333.36 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	333.14886967 g/mol
Monoisotopic Mass	333.14886967 g/mol
Topological Polar Surface Area	64.1 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	545
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of uncomplicated gonococcal urethritis in males and for gram-negative-bacterial infections in the gastrointestinal system and the genitourinary tract.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pefloxacin is a fluoroquinolone antibiotic. Flouroquinolones such as pefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.

5.2 MeSH Pharmacological Classification

Topoisomerase II Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

Cytochrome P-450 CYP1A2 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01M - Quinolone antibacterials

J01MA - Fluoroquinolones

J01MA03 - Pefloxacin

5.4 Absorption, Distribution and Excretion

Absorption

Well absorbed by the oral route.

5.5 Metabolism/Metabolites

Hepatic. Primary metabolites are pefloxacin N-oxide and norfloxacin.

5.6 Biological Half-Life

8.6 hours

5.7 Mechanism of Action

The bactericidal action of pefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.

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