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doxycycline

Go to external page http://purl.obolibrary.org/obo/CHEBI_50845

Tetracycline in which the 5beta-hydrogen is replaced by a hydroxy group, while the 6alpha-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis.

Term info

Label

doxycycline

Synonyms
  • (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
  • Doxycycline
database cross reference
Subsets

3_STAR

BRAND NAME
Jenacyclin [ DrugBank ]

BRAND NAME
Supracyclin [ DrugBank ]

INN
doxycyclinum [ ChemIDplus ]

IUPAC NAME
(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide [ IUPAC ]

INN
doxycycline [ KEGG_DRUG ]

INN
doxiciclina [ ChemIDplus ]

BRAND NAME
Vibramycin [ DrugBank ]

charge

0

formula

C22H24N2O8

has alternative id

CHEBI:42135, CHEBI:4713

has obo namespace

chebi_ontology

has related synonym

Supracyclin, (4S,4AR,5S,5AR,6R,12AS)-4-(DIMETHYLAMINO)-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE, Doxycyclin, doxycyclinum, doxycycline (anhydrous), doxiciclina, 6alpha-deoxy-5-oxytetracycline, Vibramycin, doxycycline, Jenacyclin, 5-hydroxy-alpha-6-deoxytetracycline

id

CHEBI:50845

inchi

InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1

inchikey

JBIWCJUYHHGXTC-AKNGSSGZSA-N

mass

444.43464

monoisotopicmass

444.15327

smiles

[H][C@@]12[C@@H](C)c3cccc(O)c3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O