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Cinoxacin

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ANALYTICAL

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Synopsis

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Chemistry

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Also known as: 28657-80-9, Cinobac, Compound 64716, Cinoxacino, Cinoxacinum, Cinobactin

Molecular Formula

C₁₂H₁₀N₂O₅

Molecular Weight

262.22 g/mol

InChI Key

VDUWPHTZYNWKRN-UHFFFAOYSA-N

FDA UNII

LMK22VUH23

Synthetic antimicrobial related to OXOLINIC ACID and NALIDIXIC ACID and used in URINARY TRACT INFECTIONS.

1 2D Structure

Cinoxacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-ethyl-4-oxo-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)

2.1.3 InChI Key

VDUWPHTZYNWKRN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3

2.2 Other Identifiers

2.2.1 UNII

LMK22VUH23

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Azolinic

2. Azolinic Acid

3. Cinobac

4. Clinoxacin

5. Compound 64716

2.3.2 Depositor-Supplied Synonyms

1. 28657-80-9

2. Cinobac

3. Compound 64716

4. Cinoxacino

5. Cinoxacinum

6. Cinobactin

7. Cinoxacine

8. Uronorm

9. Cinx

10. 1-ethyl-6,7-methylenedioxy-4(1h)-oxocinnoline-3-carboxylic Acid

11. Nsc 304467

12. Mls000069630

13. 1-ethyl-4-oxo-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid

14. 1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylic Acid

15. Nsc-304467

16. Lmk22vuh23

17. 1-ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid

18. Smr000058232

19. [1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid, 1-ethyl-1,4-dihydro-4-oxo-

20. Chebi:3716

21. 1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid

22. 1-ethyl-4-oxo-1,4-dihydro[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid

23. Nsc304467

24. Ncgc00015277-02

25. Cas-28657-80-9

26. Dsstox_cid_2822

27. (1,3)dioxolo(4,5-g)cinnoline-3-carboxylic Acid, 1,4-dihydro-1-ethyl-4-oxo-

28. (1,3)dioxolo(4,5-g)cinnoline-3-carboxylic Acid, 1-ethyl-1,4-dihydro-4-oxo-

29. Dsstox_rid_76745

30. Cinoxacine [inn-french]

31. Cinoxacinum [inn-latin]

32. Dsstox_gsid_22822

33. Cinoxacino [inn-spanish]

34. Lilly 64716

35. 1-ethyl-4-oxo-1h,4h,7h-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid

36. Cinobac (tn)

37. Sr-01000000129

38. Einecs 249-133-8

39. Unii-lmk22vuh23

40. Brn 1084304

41. Noxigram

42. Ccris 8206

43. Tnp00246

44. Prestwick_239

45. Cinoxacin [usan:usp:inn:ban:jan]

46. Spectrum_000152

47. Cinoxacin [inn]

48. Cinoxacin [jan]

49. Cinoxacin [mi]

50. Cinoxacin [usan]

51. Opera_id_1392

52. Prestwick0_000780

53. Prestwick1_000780

54. Prestwick2_000780

55. Prestwick3_000780

56. Spectrum2_000570

57. Spectrum3_000352

58. Spectrum4_000289

59. Spectrum5_000749

60. Cinoxacin [vandf]

61. Lopac-c-8645

62. Cinoxacin [mart.]

63. C 8645

64. Cid_2762

65. Cinoxacin [who-dd]

66. Chembl1208

67. Lopac0_000309

68. Oprea1_131085

69. Schembl43770

70. Bspbio_000860

71. Bspbio_002043

72. Kbiogr_000818

73. Kbioss_000632

74. Mls001148076

75. Divk1c_000318

76. Spectrum1500190

77. Spbio_000360

78. Spbio_002799

79. Cinoxacin (jp17/usp/inn)

80. Bpbio1_000946

81. Cinoxacin [orange Book]

82. Cinoxacin [usp Impurity]

83. Dtxsid8022822

84. Bdbm39350

85. Hms500p20

86. Kbio1_000318

87. Kbio2_000632

88. Kbio2_003200

89. Kbio2_005768

90. Kbio3_001263

91. Zinc32350

92. Ninds_000318

93. Hms1570k22

94. Hms1920o11

95. Hms2091e18

96. Hms2097k22

97. Hms2235k07

98. Hms3260n20

99. Hms3370b19

100. Hms3714k22

101. Pharmakon1600-01500190

102. Hy-b1085

103. Tox21_110121

104. Tox21_500309

105. Ccg-39160

106. Nsc756695

107. 1-ethyl-4-oxohydro-7h-1,3-dioxoleno[4,5-g]cinnoline-3-carboxylic Acid

108. Akos022507372

109. Tox21_110121_1

110. Cs-4652

111. Db00827

112. Lp00309

113. Nsc-756695

114. Sdccgsbi-0050297.p005

115. Idi1_000318

116. Cinoxacin 100 Microg/ml In Acetonitrile

117. Ncgc00015277-01

118. Ncgc00015277-03

119. Ncgc00015277-04

120. Ncgc00015277-05

121. Ncgc00015277-06

122. Ncgc00015277-07

123. Ncgc00015277-08

124. Ncgc00015277-09

125. Ncgc00015277-10

126. Ncgc00015277-11

127. Ncgc00015277-12

128. Ncgc00015277-13

129. Ncgc00015277-14

130. Ncgc00015277-17

131. Ncgc00015277-21

132. Ncgc00023754-03

133. Ncgc00023754-04

134. Ncgc00023754-05

135. Ncgc00023754-06

136. Ncgc00023754-07

137. Ncgc00260994-01

138. As-73151

139. Sbi-0050297.p004

140. Db-047427

141. Eu-0100309

142. Ft-0602947

143. Sw196546-3

144. C08052

145. D00872

146. Ab00051948_17

147. Ab00051948_18

148. A819523

149. J-017182

150. Q1639588

151. Sr-01000000129-2

152. Sr-01000000129-4

153. Sr-01000000129-7

154. Brd-k14704277-001-05-1

155. Brd-k14704277-001-15-0

156. 1-ethyl-1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid

157. Cinoxacin, United States Pharmacopeia (usp) Reference Standard

158. [1,5-g]cinnoline-3-carboxylic Acid, 1-ethyl-1,4-dihydro-4-oxo-

159. 1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylicacid

160. 1-ethyl-4-oxidanylidene-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic Acid

161. (1,3)dioxolo(4,5-g)cinnoline-3-carboxylic Acid, 1-ethyl-1,4-dihydro-4-oxo

162. 5-ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylic Acid

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₀N₂O₅
Molecular Weight	262.22 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	262.05897142 g/mol
Monoisotopic Mass	262.05897142 g/mol
Topological Polar Surface Area	88.4 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	449
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 initial and recurrent urinary tract infections in adults caused by the following susceptible microorganisms: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella species (including K. pneumoniae), and Enterobacter species.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cinoxacin is a synthetic antibacterial agent with in vitro activity against many gram-negative aerobic bacteria, particularly strains of the Enterobacteriaceae family. Cinoxacin inhibits bacterial deoxyribonucleic acid (DNA) synthesis, is bactericidal, and is active over the entire urinary pH range. Cross resistance with nalidixic acid has been demonstrated.

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-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.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01M - Quinolone antibacterials

J01MB - Other quinolones

J01MB06 - Cinoxacin

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed after oral administration. While concurrent food intake may delay the drug absorption, the total drug absorption is not affected.

5.5 Metabolism/Metabolites

Hepatic, with approximately 30-40% metabolized to inactive metabolites.

5.6 Biological Half-Life

While the mean serum half-life is 1.5 hours, the half-life may exceed 10 hours in case of renal impairment.

5.7 Mechanism of Action

Evidence exists that cinoxacin binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis. It appears to also inhibit DNA gyrase. This enzyme is necessary for proper replicated DNA separation. By inhibiting this enzyme, DNA replication and cell division is inhibited.

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