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Trovafloxacin Mesylate

Trovafloxacin Mesylate

Synopsis, Chemistry

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Also known as: Trovan, 147059-75-4, Trovafloxacin methanesulfonate, Trovafloxacin mesilate, Trovafloxacin monomethanesulfonate, Trovafloxacin (mesylate)

Molecular Formula

C₂₁H₁₉F₃N₄O₆S

Molecular Weight

512.5 g/mol

InChI Key

DYNZICQDCVYXFW-GIPYJWDTSA-N

FDA UNII

0P1LKO80WN

1 2D Structure

Trovafloxacin Mesylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid;methanesulfonic acid

2.1.2 InChI

InChI=1S/C20H15F3N4O3.CH4O3S/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24;1-5(2,3)4/h1-4,7,10-11,16H,5-6,24H2,(H,29,30);1H3,(H,2,3,4)/t10-,11+,16?;

2.1.3 InChI Key

DYNZICQDCVYXFW-GIPYJWDTSA-N

2.1.4 Canonical SMILES

CS(=O)(=O)O.C1C2C(C2N)CN1C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F

2.1.5 Isomeric SMILES

CS(=O)(=O)O.C1[C@@H]2[C@@H](C2N)CN1C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F

2.2 Other Identifiers

2.2.1 UNII

0P1LKO80WN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alatrofloxacin

2. Alatrofloxacin Mesylate

3. Cp 116,517

4. Cp 116517

5. Cp-116,517

6. Cp-116517

7. Trovan

2.3.2 Depositor-Supplied Synonyms

1. Trovan

2. 147059-75-4

3. Trovafloxacin Methanesulfonate

4. Trovafloxacin Mesilate

5. Trovafloxacin Monomethanesulfonate

6. Trovafloxacin (mesylate)

7. Cp-99219-27

8. Trovafloxacin Mesylate [usan]

9. 0p1lko80wn

10. Cp 99219

11. Chebi:77568

12. Cp-99,219-27

13. Dsstox_cid_25701

14. Dsstox_rid_81073

15. Dsstox_gsid_45701

16. 7-((1r,5s,6s)-6-amino-3-azabicyclo(3.1.0)hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, Monomethanesulfonate

17. Trovafloxacin Mesylate (usan)

18. 1,8-naphthyridine-3-carboxylic Acid, 7-[(1alpha,5alpha,6alpha)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-, Methanesulfonate (1:1)

19. Rel-7-((1r,5s,6s)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid Compound With Methanesulfonic Acid (1:1)

20. Cas-147059-75-4

21. Unii-0p1lko80wn

22. Turvel

23. Trovafloxacin Sulfate

24. Trovan (tn)

25. Cp 99219 Mesylate

26. Trovafloxacin Monomesylate

27. Ncgc00064532-02

28. Cp 99219-27

29. Schembl40874

30. Schembl40875

31. Chembl1200779

32. Dtxsid0045701

33. Hms3260e16

34. Tox21_110980

35. Tox21_500107

36. Trovafloxacin Mesylate [vandf]

37. Akos000280396

38. Akos015914051

39. Tox21_110980_1

40. Trovafloxacin Mesilate [mart.]

41. Ccg-221411

42. Trovafloxacin Mesilate [who-dd]

43. Trovafloxacin Mesylate, >98% (hplc)

44. Ncgc00260792-01

45. Ncgc00263538-01

46. 1,8-naphthyridine-3-carboxylic Acid, 7-(6-amino-3-azabicyclo(3.1.0)hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-(1alpha,5alpha,6alpha)-, Monomethanesulfonate

47. Trovafloxacin Methanesulfonate [mi]

48. Hy-103399

49. Trovafloxacin Mesylate [orange Book]

50. Cs-0027824

51. D02123

52. E98675

53. J-008308

54. J-690188

55. Q27147183

56. (1r,5s,6s)-3-[6-carboxy-8-(2,4-difluorophenyl)-3-fluoro-5-oxo-5,8-dihydro-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hexan-6-aminium Methanesulfonate

57. 1,8-naphthyridine-3-carboxylic Acid, 7-((1.alpha.,5.alpha.,6.alpha.)-6-amino-3-azabicyclo(3.1.0)hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-, Methanesulfonate (1:1)

58. 1,8-naphthyridine-3-carboxylic Acid, 7-(6-amino-3-azabicyclo(3.1.0)hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-(1.alpha.,5.alpha.,6.alpha.)- Monomethanesulfonate

59. 171335-83-4

60. 7-((1r,5s,6s)-6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid Compound With Methanesulfonic Acid (1:1)

61. 7-[(1?,5?,6?)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid Mesylate

62. 7-[(1r,5s,6s)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid Methanesulfonate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₉F₃N₄O₆S
Molecular Weight	512.5 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	3
Exact Mass	512.09774000 g/mol
Monoisotopic Mass	512.09774000 g/mol
Topological Polar Surface Area	163 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	863
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

Trovafloxacin is a synthetic broad spectrum quinolone antibacterial agent indicated for the treatment of the following infections in adults:

- Pneumonia: Community Acquired Pneumonia and Nosocomial Pneumonia (mild, moderate, and severe).

Note: Efficacy in patients with very severe nosocomial pneumonia and in particular infections due to less susceptible pathogens e. g. P. aeruginosa, has not been established. See also section 4. 2.

- Acute Exacerbations of Chronic Bronchitis

- Acute Sinusitis

- Complicated Intra-abdominal Infections and Acute Pelvic Infections

- Salpingitis

- Uncomplicated Gonococcal Urethritis and Cervicitis

- Chlamydial Cervicitis

- Complicated Skin and Soft Tissue Infections

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

Trovafloxacin is a synthetic broad spectrum quinolone antibacterial agent indicated for the treatment of the following infections in adults:

Pneumonia:

- Community Acquired Pneumonia and Nosocomial Pneumonia (mild, moderate, and severe).

Note: Efficacy in patients with very severe nosocomial pneumonia and in particular infections due to less susceptible pathogens e. g. P. aeruginosa, has not been established. See also section 4. 2.

- Acute Exacerbations of Chronic Bronchitis

- Acute Sinusitis

- Complicated Intra-abdominal Infections and Acute Pelvic Infections

- Salpingitis

- Uncomplicated Gonococcal Urethritis and Cervicitis

- Chlamydial Cervicitis

- Complicated Skin and Soft Tissue Infections

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

5 Pharmacology and Biochemistry

5.1 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.)

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.)

5.2 ATC Code

J01MA13