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CHEBI:75246 - rifaximin

Default Structure
ChEBI IDCHEBI:75246
ChEBI Namerifaximin
Stars
DefinitionA 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.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC43H51N3O11
Net Charge0
Average Mass785.891
Monoisotopic Mass785.35236
SMILESCO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c5c(nc6cc(C)ccn65)c4c3C2=O)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
InChIInChI=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
InChIKeyNZCRJKRKKOLAOJ-XRCRFVBUSA-N
Wikipedia
Roles Classification
Biological Role:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
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.
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
rifaximinKEGG DRUG
rifaximinaDrugBank
rifaximineDrugBank
rifaximinunDrugBank
Synonyms  Source
Rifamycin L 105DrugBank
Rifamycin L 105SVDrugBank
RifaxidinDrugBank
Brand Name  Source
XifaxsanKEGG DRUG
Manual XrefsDatabases
2379DrugCentral
D02554KEGG DRUG
DB01220DrugBank
HMDB0015351HMDB
RifaximinWikipedia
Registry NumbersSources
Reaxys:7790802Reaxys
CAS:80621-81-4ChemIDplus
CAS:80621-81-4KEGG DRUG
Citations