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Synopsis

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Chemistry

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Also known as: 79660-72-3, Megalone, Megalocin, Fleroxicin, Quinodis, Fleroxacino

Molecular Formula

C₁₇H₁₈F₃N₃O₃

Molecular Weight

369.34 g/mol

InChI Key

XBJBPGROQZJDOJ-UHFFFAOYSA-N

FDA UNII

N804LDH51K

A broad-spectrum antimicrobial fluoroquinolone. The drug strongly inhibits the DNA-supercoiling activity of DNA GYRASE.

1 2D Structure

Fleroxacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)

2.1.3 InChI Key

XBJBPGROQZJDOJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)C2=C(C=C3C(=C2F)N(C=C(C3=O)C(=O)O)CCF)F

2.2 Other Identifiers

2.2.1 UNII

N804LDH51K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Am 833

2. Am-833

3. Am833

4. Quinodis

5. Ro 23 6240

6. Ro 23-6240

7. Ro 236240

2.3.2 Depositor-Supplied Synonyms

1. 79660-72-3

2. Megalone

3. Megalocin

4. Fleroxicin

5. Quinodis

6. Fleroxacino

7. Fleroxacinum

8. 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

9. Fleroxacine

10. Am-833

11. Ro 23-6240

12. Ro 23-6240/000

13. Flrx

14. Fleroxacin (quinodis)

15. Ro-236240

16. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic Acid

17. Chebi:31810

18. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

19. Ro-236240000

20. N804ldh51k

21. 3-quinolinecarboxylic Acid, 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-

22. Ro-23-6240/000

23. Ncgc00167558-01

24. Fleroxacine [french]

25. Fleroxacinum [latin]

26. Fleroxacino [spanish]

27. Ro 23-6240;am-833

28. Am 833

29. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic Acid

30. Dsstox_cid_26714

31. Dsstox_rid_81846

32. Dsstox_gsid_46714

33. Megalosin

34. Megalocin (tn)

35. Megalone (tn)

36. Smr000466302

37. Cas-79660-72-3

38. Ccris 3972

39. Sr-01000759379

40. Brn 4300996

41. Unii-n804ldh51k

42. Fleroxacin (jan/usan/inn)

43. Fleroxacin,(s)

44. Fleroxacin [usan:inn:ban:jan]

45. Mfcd00864880

46. Fleroxacin [mi]

47. Fleroxacin [inn]

48. Fleroxacin [jan]

49. Fleroxacin [usan]

50. F0646

51. Fleroxacin [mart.]

52. Chembl6273

53. Fleroxacin [who-dd]

54. Schembl48145

55. Mls000759401

56. Mls006010715

57. Dtxsid1046714

58. Hms2090i08

59. Hms3715b11

60. Bcp28939

61. Hy-b0414

62. Rkl10075

63. Zinc3786299

64. Tox21_112553

65. Bdbm50247892

66. S2469

67. Zinc03786299

68. Akos015907011

69. Fleroxacin 100 Microg/ml In Methanol

70. Tox21_112553_1

71. Ccg-221125

72. Db04576

73. Ks-5124

74. Ncgc00167558-02

75. 3-quinolinecarboxylic Acid, 1,4-dihydro-6,8-difluoro-1-(2-fluoroethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-

76. Am-833;am833;am 833

77. Fleroxacin 100 Microg/ml In Acetonitrile

78. Ft-0630874

79. D01716

80. Fleroxacin, Vetranal(tm), Analytical Standard

81. Ab00640001-02

82. Ab00640001-03

83. Ab00640001_04

84. 660f723

85. A839732

86. Q3746573

87. Sr-01000759379-2

88. Sr-01000759379-3

89. 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid-

90. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylicacid

91. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic Acid;fleroxacin

92. 79660-53-0

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₈F₃N₃O₃
Molecular Weight	369.34 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	4
Exact Mass	369.13002593 g/mol
Monoisotopic Mass	369.13002593 g/mol
Topological Polar Surface Area	64.1 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	595
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

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone. It strongly inhibits the DNA-supercoiling activity of DNA gyrase.

5.2 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

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.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01M - Quinolone antibacterials

J01MA - Fluoroquinolones

J01MA08 - Fleroxacin

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly and well absorbed from the gastrointestinal tract after oral administration.

5.5 Mechanism of Action

The inhibition of DNA gyrase and DNA topoisomerase 2 leads ultimately to cell death as these enzymes are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.

Drugs in Development