CHEBI:4392 - demeclocycline

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ChEBI Name demeclocycline
ChEBI ID CHEBI:4392
Definition Tetracycline 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:554084
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Formula C21H21ClN2O8
Net Charge 0
Average Mass 464.85300
Monoisotopic Mass 464.099
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
InChIKey FMTDIUIBLCQGJB-SEYHBJAFSA-N
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
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via tetracyclines )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing demeclocycline (CHEBI:4392) has role antibacterial drug (CHEBI:36047)
demeclocycline (CHEBI:4392) is a tetracyclines (CHEBI:26895)
Incoming 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 Sources
demeclociclina ChemIDplus
demeclocycline ChemIDplus
demeclocyclinum ChemIDplus
Synonyms Sources
6-demethyl-7-chlorotetracycline ChemIDplus
7-chloro-6-demethyltetracycline ChEBI
[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-naphthacenecarboxamide ChEBI
Demeclocycline ChEMBL
demethylchlortetracycline KEGG DRUG
DMCT ChemIDplus
DMCTC KEGG DRUG
Manual Xrefs Databases
802 DrugCentral
D00290 KEGG DRUG
D03680 KEGG DRUG
DB00618 DrugBank
Demeclocycline Wikipedia
FR1344645 Patent
US2878289 Patent
US3012946 Patent
US3019172 Patent
US3050446 Patent
US3154476 Patent
View more database links
Registry Numbers Types Sources
127-33-3 CAS Registry Number ChemIDplus
127-33-3 CAS Registry Number KEGG DRUG
2230579 Beilstein Registry Number Beilstein
Last Modified
22 February 2017