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CAS 57-62-5

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Chlortetracycline

Description:
Chlortetracycline is a broad-spectrum antibiotic belonging to the tetracycline class, primarily used to treat bacterial infections in both humans and animals. It is characterized by its yellow crystalline appearance and is soluble in water, which facilitates its use in various formulations. The chemical structure of chlortetracycline includes a naphthacene core with multiple hydroxyl and dimethylamino groups, contributing to its antibacterial activity by inhibiting protein synthesis in bacteria. Its mechanism of action involves binding to the 30S ribosomal subunit, preventing the attachment of aminoacyl-tRNA and thereby disrupting the translation process. Chlortetracycline is effective against a wide range of Gram-positive and Gram-negative bacteria, as well as some protozoa. However, its use has declined due to the emergence of antibiotic resistance and the availability of newer antibiotics with improved efficacy and safety profiles. Additionally, it is important to note that chlortetracycline can cause side effects, including gastrointestinal disturbances and photosensitivity, and its use is regulated in food-producing animals to minimize antibiotic residues in food products.
Formula:C22H23ClN2O8
InChI:InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1
InChI key:InChIKey=CYDMQBQPVICBEU-XRNKAMNCSA-N
SMILES:O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)(C[C@]3(C(=C2O)C(=O)C=4C([C@@]3(C)O)=C(Cl)C=CC4O)[H])[H]
Synonyms:
  • (4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
  • 10,12,12A-Pentahydroxy-6-Methyl-1,11-Dioxo-Ydro-6
  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-
  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-
  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, [4S-(4α,4aα,5aα,6β,12aα)]-
  • 4-(Dimethylamino)-7-chloro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,5,6,12a,4a,5a-hexahydronaphthacene-2-carboxamide
  • 7-Chloro-4-(Dimethylamino)-3,6,10,12,12A-Pentahydroxy-6-Methyl-1,11-Dioxo-1,4,4A,5,5A,6,11,12A-Octahydrotetracene-2-Carboxamide
  • 7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
  • 7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-naphthacenecarboxamide
  • 7-Chloro-4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
  • See more synonyms
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