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Gatifloxacin Anhydrous

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Synopsis

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6EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 112811-59-3, Tequin, Gatiflo, Zymar, Am-1155, Zymaxid

Molecular Formula

C₁₉H₂₂FN₃O₄

Molecular Weight

375.4 g/mol

InChI Key

XUBOMFCQGDBHNK-UHFFFAOYSA-N

FDA UNII

81485Y3A9A

A fluoroquinolone antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used as an ophthalmic solution for the treatment of BACTERIAL CONJUNCTIVITIS.

Gatifloxacin anhydrous is a Quinolone Antimicrobial.

1 2D Structure

Gatifloxacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)

2.1.3 InChI Key

XUBOMFCQGDBHNK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F

2.2 Other Identifiers

2.2.1 UNII

81485Y3A9A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

2. Am 1155

3. Am-1155

4. Bms 206584

5. Bms-206584

6. Bms206584

7. Cg 5501

8. Gatifloxacine

9. Tequin

10. Zymar

2.3.2 Depositor-Supplied Synonyms

1. 112811-59-3

2. Tequin

3. Gatiflo

4. Zymar

5. Am-1155

6. Zymaxid

7. Gatifloxacin Anhydrous

8. Am 1155

9. Zymer

10. Cg 5501

11. 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

12. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

13. Bms-206584

14. Gtfx

15. Bms 206584-01

16. Pd 135432

17. 1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

18. Gatifloxacin Hydrate

19. Gatifloxacin (inn)

20. Chembl31

21. 3-quinolinecarboxylic Acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-

22. Nsc-758701

23. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic Acid

24. Pd-135432

25. Chebi:5280

26. Gatilox

27. Gatiquin

28. Gatispan

29. 160738-57-8

30. Gaity

31. Cg5501

32. Mfcd00895399

33. 81485y3a9a

34. Gatifloxin

35. Ncgc00068236-02

36. Gatifloxacin 100 Microg/ml In Acetonitrile

37. Gatifloxacin [inn]

38. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic Acid

39. Dsstox_cid_25704

40. Dsstox_rid_81076

41. Dsstox_gsid_45704

42. Gatifloxacin [usan:inn]

43. Bms-206584-01

44. Bonoq

45. Gatifloxacin (sesquihydrate)

46. Tymer

47. 1-cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic Acid

48. 3-quinolinecarboxylic Acid,1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-

49. Smr000043336

50. Gatifloxacin (tn)

51. Cas-112811-59-3

52. Zymer (tn)

53. 1-cyclopropyl-6-fluoro-8-methoxy-7-

54. Sr-01000610458

55. (3-methylpiperazin-1-yl)-4-oxo-1,4-

56. Bms-20658401

57. Gatifloxacino

58. Gatifloxacinum

59. Gatifloxcin

60. Tequin In Dextrose 5% In Plastic Container

61. Am-1155 (*sesquihydrate*)

62. Gatifloxacin & Gamma Interferon

63. Unii-81485y3a9a

64. Gatifloxacin,(s)

65. (+-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

66. Cg-5501

67. Kinome_3137

68. Spectrum_001909

69. Cpd000043336

70. Pd135432

71. Spectrum2_000487

72. Spectrum3_000999

73. Spectrum4_001127

74. Spectrum5_001468

75. Gatifloxacin [mi]

76. Schembl22591

77. Bspbio_002697

78. Kbiogr_001613

79. Kbioss_002448

80. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

81. Mls000040259

82. Mls000759493

83. Mls006011836

84. Gatifloxacin [who-dd]

85. Spectrum1504272

86. Spbio_000353

87. Gatifloxacin Sesquihydrate,(s)

88. Dtxsid5045704

89. Gtpl10816

90. Kbio2_002442

91. Kbio2_005010

92. Kbio2_007578

93. Kbio3_001917

94. Hms1922j15

95. Hms2090k10

96. Hms2093g06

97. Hms2233d20

98. Hms3259p06

99. Hms3372j10

100. Hms3372j12

101. Hms3715n03

102. Pharmakon1600-01504272

103. Albb-028535

104. Amy17781

105. Bcp13408

106. Rkl10068

107. Tox21_110984

108. Bbl010485

109. Bdbm50117914

110. Ccg-39529

111. Nsc758701

112. S1340

113. Stk801620

114. C19h22fn3o4.1.5h2o

115. Akos004119932

116. Akos016340697

117. Tox21_110984_1

118. Ac-1944

119. Cs-1841

120. Db01044

121. Ks-1066

122. Nc00702

123. Nsc 758701

124. Gatifloxacin 100 Microg/ml In Methanol

125. Ncgc00068236-03

126. Ncgc00068236-04

127. Ncgc00068236-05

128. Ncgc00068236-06

129. Ncgc00068236-07

130. Ncgc00068236-08

131. Ncgc00095126-01

132. Ncgc00095126-02

133. Ncgc00178525-01

134. Hy-10581

135. Sbi-0206764.p001

136. Db-019145

137. Ft-0626635

138. Ft-0631189

139. Ft-0668952

140. G0325

141. C07661

142. D08011

143. G-2380

144. Ab00171654-13

145. Ab00171654-14

146. Ab00171654_16

147. Ab00171654_17

148. 811g593

149. A802657

150. Gatifloxacin, Antibiotic For Culture Media Use Only

151. Q2365016

152. Sr-01000610458-2

153. Sr-01000610458-3

154. Brd-a74980173-001-02-8

155. Brd-a74980173-001-06-9

156. (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

157. 1-cyclopropyl-6-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylic Acid

158. 1-cyclopropyl-6-6-fluoro-1,4-dihydro-8-methoxy-7-(3methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylic Acid

159. 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylic Acid

160. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

161. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylicacid

162. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic A

163. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic Acid

164. 1-cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₂FN₃O₄
Molecular Weight	375.4 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	375.15943435 g/mol
Monoisotopic Mass	375.15943435 g/mol
Topological Polar Surface Area	82.1 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	653
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Gatifloxacin
PubMed Health	Gatifloxacin (Into the eye)
Drug Classes	Antibiotic
Drug Label	ZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
Active Ingredient	Gatifloxacin
Dosage Form	Solution/drops; Solution
Route	Ophthalmic; ophthalmic
Strength	0.5%; 0.3%
Market Status	Tentative Approval; Prescription
Company	Hi-tech Pharma; Lupin; Hi-tech Pharmacal

2 of 6
Drug Name	Zymar
PubMed Health	Gatifloxacin (Into the eye)
Drug Classes	Antibiotic
Drug Label	ZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
Active Ingredient	Gatifloxacin
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.3%
Market Status	Prescription
Company	Allergan

3 of 6
Drug Name	Zymaxid
Active Ingredient	Gatifloxacin
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%
Market Status	Prescription
Company	Allergan

4 of 6
Drug Name	Gatifloxacin
PubMed Health	Gatifloxacin (Into the eye)
Drug Classes	Antibiotic
Drug Label	ZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
Active Ingredient	Gatifloxacin
Dosage Form	Solution/drops; Solution
Route	Ophthalmic; ophthalmic
Strength	0.5%; 0.3%
Market Status	Tentative Approval; Prescription
Company	Hi-tech Pharma; Lupin; Hi-tech Pharmacal

5 of 6
Drug Name	Zymar
PubMed Health	Gatifloxacin (Into the eye)
Drug Classes	Antibiotic
Drug Label	ZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
Active Ingredient	Gatifloxacin
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.3%
Market Status	Prescription
Company	Allergan

6 of 6
Drug Name	Zymaxid
Active Ingredient	Gatifloxacin
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%
Market Status	Prescription
Company	Allergan

4.2 Drug Indication

For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.

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.)

Anti-Bacterial Agents

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

Ophthalmic Solutions

Sterile solutions that are intended for instillation into the eye. It does not include solutions for cleaning eyeglasses or CONTACT LENS SOLUTIONS. (See all compounds classified as Ophthalmic Solutions.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

GATIFLOXACIN ANHYDROUS

5.3.2 FDA UNII

81485Y3A9A

5.3.3 Pharmacological Classes

Quinolones [CS]; Quinolone Antimicrobial [EPC]

5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01M - Quinolone antibacterials

J01MA - Fluoroquinolones

J01MA16 - Gatifloxacin

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AE - Fluoroquinolones

S01AE06 - Gatifloxacin

5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%

5.6 Metabolism/Metabolites

Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites

5.7 Biological Half-Life

7-14 hours

5.8 Mechanism of Action

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

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