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DSSTox_CID_3590

DSSTox_CID_3590

Synopsis, Chemistry

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Also known as: 110871-86-8, Zagam, At-4140, Ci-978, Spara, Ci 978

Molecular Formula

C₁₉H₂₂F₂N₄O₃

Molecular Weight

392.4 g/mol

InChI Key

DZZWHBIBMUVIIW-DTORHVGOSA-N

FDA UNII

Q90AGA787L

Sparfloxacin is a fluoroquinolone antibiotic that inhibits bacterial DNA gyrase, thereby inhibiting DNA replication and transcription. Sparfloxacin was withdrawn from the U.S. market due to a high incidence of phototoxicity.

1 2D Structure

DSSTox_CID_3590

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+

2.1.3 InChI Key

DZZWHBIBMUVIIW-DTORHVGOSA-N

2.1.4 Canonical SMILES

CC1CN(CC(N1)C)C2=C(C(=C3C(=C2F)N(C=C(C3=O)C(=O)O)C4CC4)N)F

2.1.5 Isomeric SMILES

C[C@@H]1CN(C[C@@H](N1)C)C2=C(C(=C3C(=C2F)N(C=C(C3=O)C(=O)O)C4CC4)N)F

2.2 Other Identifiers

2.2.1 UNII

Q90AGA787L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)- 6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

2. At 4140

3. At-4140

4. Ci 978

5. Ci-978

6. Pd 131501

7. Pd-131501

8. Zagam

2.3.2 Depositor-Supplied Synonyms

1. 110871-86-8

2. Zagam

3. At-4140

4. Ci-978

5. Spara

6. Ci 978

7. Spfx

8. Pd 131501

9. Pd-131501

10. At 4140

11. 111542-93-9

12. Chebi:9212

13. 5-amino-1-cyclopropyl-7-((3s,5r)-3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

14. 5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

15. 5-amino-1-cyclopropyl-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

16. Q90aga787l

17. 5-amino-1-cyclopropyl-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic Acid

18. Cis-5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

19. Esparfloxacino

20. Sparfloxacine

21. Sparfloxacinum

22. Nsc-759641

23. Mfcd00869619

24. Dsstox_cid_3590

25. Dsstox_rid_77097

26. Dsstox_gsid_23590

27. 3-quinolinecarboxylic Acid, 5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-, Cis-

28. 5-amino-1-cyclopropyl-7-((3r,5s)-3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

29. 5-amino-1-cyclopropyl-7-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic Acid

30. Sparfloxacine [inn-french]

31. Sparfloxacinum [inn-latin]

32. Drg-0143

33. Esparfloxacino [inn-spanish]

34. Parox

35. Cas-110871-86-8

36. Zagam (tn)

37. Cp 103826

38. Sr-05000001521

39. Brn 3658018

40. Unii-q90aga787l

41. Sparfloxacin & Ru 40555

42. Pd 1315-1

43. Sparfloxacin (jan/usan/inn)

44. Liposome-encapsulated Sparfloxacin

45. Sparfloxacin,(s)

46. Ncgc00159333-02

47. Sparfloxacin [usan:inn:ban:jan]

48. Sparfloxacinhydrochloride

49. Pd131501

50. Rp-64206

51. Cp-103826

52. Sparfloxacin [mi]

53. Sparfloxacin [inn]

54. Sparfloxacin [jan]

55. Chembl850

56. Epitope Id:119065

57. Sparfloxacin [usan]

58. Sparfloxacin [vandf]

59. Schembl41311

60. Sparfloxacin [mart.]

61. Mls000759417

62. Sparfloxacin [who-dd]

63. Dtxsid9023590

64. Gtpl10860

65. Ci978

66. Hms2090n19

67. Hms3715j13

68. Sparfloxacin [orange Book]

69. Zinc538362

70. Bcp23886

71. Hy-b0308

72. Rkl10082

73. Sparfloxacin, >=98.0% (hplc)

74. Tox21_111580

75. At4140

76. Bbl010957

77. Bdbm50366822

78. S1884

79. Stk802067

80. Akos005622503

81. Tox21_111580_1

82. Ccg-221166

83. Db01208

84. Ks-5009

85. Nsc 759641

86. Sparfloxacin 100 Microg/ml In Methanol

87. Ncgc00166294-01

88. Ncgc00166294-02

89. Ncgc00166294-03

90. 3-quinolinecarboxylic Acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-7-(3,5-dimethyl-1-piperazinyl)-4-oxo-, Cis-

91. Ac-11574

92. Smr000466312

93. S0896

94. Sw199632-2

95. C07662

96. D00590

97. S-6990

98. Ab00639950-02

99. Ab00639950_03

100. Sparfloxacin, Vetranal(tm), Analytical Standard

101. 871s868

102. A802376

103. A894831

104. Q976559

105. Sr-01000759357

106. Sparfloxacin, Antibiotic For Culture Media Use Only

107. Sr-01000759357-2

108. Sr-05000001521-1

109. Sr-05000001521-2

110. Brd-k07612980-001-07-9

111. 4-bromo-1-(tert-butyl)-3-methyl-1h-pyrazole-5-carboxylicacid

112. 5-amino-1-cyclopropyl-6,8-difluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

113. 5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl)-6,8- Difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid & Ru 40555

114. 5-amino-1-cyclopropyl-7-(cis-3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

115. 5-amino-1-cyclopropyl-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic Acid

116. 5-amino-1-cyclopropyl-7-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic Acid

117. 5-amino-1-cyclopropyl-7-[(3s,5r)-3,5-dimethylpiperazin-4-ium-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylate

118. At-4140 Pound>>ci-978 Pound>>ci 978 Pound>>ci978 Pound>>at 4140 Pound>>at4140 Pound>>pd 131501 Pound>>pd131501 Pound>>pd-131501

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₂F₂N₄O₃
Molecular Weight	392.4 g/mol
XLogP3	0.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	392.16599690 g/mol
Monoisotopic Mass	392.16599690 g/mol
Topological Polar Surface Area	98.9 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	691
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	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of adults with the following infections caused by susceptible strains microorganisms: community-acquired pneumonia (caused by Chlamydia pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, or Streptococcus pneumoniae) and acute bacterial exacerbations of chronic bronchitis (caused by Chlamydia pneumoniae, Enterobacter cloacae, Haemophilus influenzae, Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis, Staphylococcus aureus, or Streptococcus pneumoniae).

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sparfloxacin is a synthetic fluoroquinolone broad-spectrum antimicrobial agent in the same class as ofloxacin and norfloxacin. Sparfloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription. Quinolones differ in chemical structure and mode of action from (beta)-lactam antibiotics. Quinolones may, therefore, be active against bacteria resistant to (beta)-lactam antibiotics. Although cross-resistance has been observed between sparfloxacin and other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to sparfloxacin. In vitro tests show that the combination of sparfloxacin and rifampin is antagonistic against Staphylococcus aureus.

5.2 MeSH Pharmacological Classification

Antitubercular Agents

Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular 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

J01MA09 - Sparfloxacin

5.4 Absorption, Distribution and Excretion

Absorption

Well absorbed following oral administration with an absolute oral bioavailability of 92%. Unaffected by administration with milk or food, however concurrent administration of antacids containing magnesium hydroxide and aluminum hydroxide reduces the oral bioavailability of sparfloxacin by as much as 50%.

5.5 Metabolism/Metabolites

Hepatic. Metabolized primarily by phase II glucuronidation to form a glucuronide conjugate. Metabolism does not utilize or interfere with the cytochrome P450 enzyme system.

5.6 Biological Half-Life

Mean terminal elimination half-life of 20 hours (range 16-30 hours). Prolonged in patients with renal impairment (creatinine clearance <50 mL/min).

5.7 Mechanism of Action

The bactericidal action of sparfloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.