CHEBI:149836 - tigecycline

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ChEBI Name tigecycline
ChEBI ID CHEBI:149836
Definition Tetracycline in which the hydroxy group at position 5 and the methyl group at position 6 are replaced by hydrogen, and with a dimethylamino substituent and an (N-tert-butylglycyl)amino substituent at positions 7 and 9, respectively. A glycylcycline antibiotic, it has activity against a broad range of Gram-positive and Gram-negative bacteria, including tetracycline-resistant organisms. It is used for the intravenous treatment of complicated skin and skin structure infections caused by susceptible organisms.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:473970, CHEBI:29696
Supplier Information
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Formula C29H39N5O8
Net Charge 0
Average Mass 585.64870
Monoisotopic Mass 585.280
InChI InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1
InChIKey FPZLLRFZJZRHSY-HJYUBDRYSA-N
SMILES [H][C@@]12Cc3c(cc(NC(=O)CNC(C)(C)C)c(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])C2)N(C)C
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 tigecycline (CHEBI:149836) has role antibacterial drug (CHEBI:36047)
tigecycline (CHEBI:149836) is a tertiary α-hydroxy ketone (CHEBI:139592)
tigecycline (CHEBI:149836) is a tetracyclines (CHEBI:26895)
IUPAC Name
(4S,4aS,5aR,12aS)-9-[(N-tert-butylglycyl)amino]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Synonym Source
(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide ChemIDplus
Manual Xrefs Databases
2661 DrugCentral
C12012 KEGG COMPOUND
D01079 KEGG DRUG
DB00560 DrugBank
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Registry Numbers Types Sources
220620-09-7 CAS Registry Number KEGG COMPOUND
220620-09-7 CAS Registry Number ChemIDplus
8379453 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17194827 PubMed citation ChEMBL
17210772 PubMed citation ChEMBL
17220399 PubMed citation ChEMBL
17307973 PubMed citation ChEMBL
17353238 PubMed citation ChEMBL
17353249 PubMed citation ChEMBL
Last Modified
07 February 2018