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CAS 127-33-3

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Demeclocycline

Description:
Demeclocycline is a tetracycline antibiotic that is primarily used to treat various bacterial infections. It is characterized by its broad-spectrum activity against both Gram-positive and Gram-negative bacteria, making it effective in treating conditions such as respiratory tract infections, urinary tract infections, and certain skin infections. The chemical structure of demeclocycline includes a naphthacene core, which is typical of tetracyclines, and it possesses a unique chloro substitution that enhances its antibacterial properties. Demeclocycline is also known for its ability to inhibit protein synthesis in bacteria by binding to the 30S ribosomal subunit. Additionally, it has been used off-label for the treatment of conditions like acne and as an adjunct therapy in the management of certain types of kidney disorders. However, its use has declined due to the emergence of antibiotic resistance and the availability of newer antibiotics with improved safety profiles. Side effects may include gastrointestinal disturbances, photosensitivity, and potential effects on bone and teeth development in children.
Formula:C21H21ClN2O8
InChI:InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1
InChI key:InChIKey=FMTDIUIBLCQGJB-SEYHBJAFSA-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@H]3O)=C(Cl)C=CC4O)[H])[H]
Synonyms:
  • (2E,4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
  • (2Z,4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
  • (4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide
  • (4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
  • (4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride (1:1)
  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-
  • 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-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-1,11-dioxo-, [4S-(4α,4aα,5aα,6β,12aα)]-
  • 6-Demethyl-7-chlorotetracycline
  • 6-Demethyl-7-chlortetracycline
  • See more synonyms
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