CHEBI:75246 - rifaximin

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ChEBI Name rifaximin
ChEBI ID CHEBI:75246
Definition A semisynthetic member of the class of rifamycins and non-systemic gastrointestinal site-specific broad spectrum antibiotic. Used in the treatment of traveller's diarrhoea, hepatic encephalopathy and irritable bowel syndrome.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C43H51N3O11
Net Charge 0
Average Mass 785.87850
Monoisotopic Mass 785.352
InChI InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
InChIKey NZCRJKRKKOLAOJ-XRCRFVBUSA-N
SMILES CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c1c(nc5cc(C)ccn15)c4c3C2=O
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application(s): orphan drug
Any drug that has been developed specifically for treatment of a rare medical condition, the condition itself being known as an orphan disease.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
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ChEBI Ontology
Outgoing rifaximin (CHEBI:75246) has role antimicrobial agent (CHEBI:33281)
rifaximin (CHEBI:75246) has role gastrointestinal drug (CHEBI:55324)
rifaximin (CHEBI:75246) has role orphan drug (CHEBI:71031)
rifaximin (CHEBI:75246) is a acetate ester (CHEBI:47622)
rifaximin (CHEBI:75246) is a cyclic ketal (CHEBI:59779)
rifaximin (CHEBI:75246) is a lactam (CHEBI:24995)
rifaximin (CHEBI:75246) is a macrocycle (CHEBI:51026)
rifaximin (CHEBI:75246) is a organic heterohexacyclic compound (CHEBI:51914)
rifaximin (CHEBI:75246) is a rifamycins (CHEBI:26580)
rifaximin (CHEBI:75246) is a semisynthetic derivative (CHEBI:72588)
IUPAC Name
(2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-1,15-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)furo[2'',3'':7',8']naphtho[1',2':4,5]imidazo[1,2-a]pyridin-25-yl acetate
INNs Sources
rifaximin KEGG DRUG
rifaximina DrugBank
rifaximine DrugBank
rifaximinun DrugBank
Synonyms Sources
Rifamycin L 105 DrugBank
Rifamycin L 105SV DrugBank
Rifaxidin DrugBank
Brand Name Source
Xifaxsan KEGG DRUG
Database Links Databases
2379 DrugCentral
D02554 KEGG DRUG
DB01220 DrugBank
HMDB0015351 HMDB
Rifaximin Wikipedia
View more database links
Registry Numbers Types Sources
7790802 Reaxys Registry Number Reaxys
80621-81-4 CAS Registry Number ChemIDplus
80621-81-4 CAS Registry Number KEGG DRUG
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Last Modified
22 February 2017