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    Technical details about MolPort-001-794-447, learn more about the structure, uses, toxicity, action, side effects and more

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    MolPort-001-794-447

    APIs // Active Pharmaceutical Ingredients

    INTERMEDIATES

    DOSSIERs // Finished Dosage Forms

    GLOBAL SALES INFORMATION

    ANALYTICAL SOLUTION(s)

    DIGITAL CONTENT

    PharmaCompass

    Phyton is a World Leader in Plant Cell Fermentation Technology and Commercial Manufacturing.

    Athena Pharmaceutiques is a Partner of Choice for Drug Delivery & Life Cycle Management.

    2D Structure
    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

    2D Structure

    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 Weight 262.22 g/mol
    Molecular Formula C12H10N2O5
    XLogP32.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass262.05897142 g/mol
    Monoisotopic Mass262.05897142 g/mol
    Topological Polar Surface Area88.4 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity449
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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