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CHEBI:4392 - demeclocycline

Default Structure
ChEBI IDCHEBI:4392
ChEBI Namedemeclocycline
Stars
DefinitionTetracycline which lacks the methyl substituent at position 7 and in which the hydrogen para- to the phenolic hydroxy group is substituted by chlorine. Like tetracycline, it is an antibiotic, but being excreted more slowly, effective blood levels are maintained for longer. It is used (mainly as the hydrochloride) for the treatment of Lyme disease, acne and bronchitis, as well as for hyponatraemia (low blood sodium concentration) due to the syndrome of inappropriate antidiuretic hormone (SIADH) where fluid restriction alone has been ineffective.
Secondary ChEBI IDCHEBI:554084
Last Modified20 February 2023
DownloadsMolfile
FormulaC21H21ClN2O8
Net Charge0
Average Mass464.858
Monoisotopic Mass464.09864
SMILES[H][C@]12C[C@@]3([H])[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C(=O)c1c(O)ccc(Cl)c1[C@H]2O
InChIInChI=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
InChIKeyFMTDIUIBLCQGJB-SEYHBJAFSA-N
Wikipedia
Roles Classification
Biological Roles:
antibacterial drug  A drug used to treat or prevent bacterial infections.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
aquaretic  A class of diuretics which promote aquaresis (the excretion of water without electrolyte loss).
antibacterial drug  A drug used to treat or prevent bacterial infections.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
demeclocycline (CHEBI:4392) has role antibacterial agent (CHEBI:33282)
demeclocycline (CHEBI:4392) has role antibacterial drug (CHEBI:36047)
demeclocycline (CHEBI:4392) has role aquaretic (CHEBI:194423)
demeclocycline (CHEBI:4392) has role geroprotector (CHEBI:176497)
demeclocycline (CHEBI:4392) is a tetracyclines (CHEBI:26895)
Incoming Relation(s)
demeclocycline hydrochloride (CHEBI:59725) has part demeclocycline (CHEBI:4392)
IUPAC Name 
(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
INNs  Source
demeclociclinaChemIDplus
demeclocyclineChemIDplus
demeclocyclinumChemIDplus
Synonyms  Source
[4S-(4α,4aα,5aα,6β,12aα)]-7-chloro-4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamideChEBI
6-demethyl-7-chlorotetracyclineChemIDplus
7-chloro-6-demethyltetracyclineChEBI
DemeclocyclineChEMBL
demethylchlortetracyclineKEGG DRUG
DMCTChemIDplus
Manual XrefsDatabases
10482117ChemSpider
802DrugCentral
D00290KEGG DRUG
D03680KEGG DRUG
DB00618DrugBank
DemeclocyclineWikipedia
FR1344645Patent
US2878289Patent
US3012946Patent
US3019172Patent
US3050446Patent
US3154476Patent
Registry NumbersSources
Beilstein:2230579Beilstein
CAS:127-33-3KEGG COMPOUND
CAS:127-33-3ChemIDplus
CAS:127-33-3KEGG DRUG
Citations