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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 Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Applications:
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
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.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
anti-anaemic agent  A compound which increases either the number of red cells or the amount of haemoglobin in the blood.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
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.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
antispasmodic drug  A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
rifaximin (CHEBI:75246) has role anti-anaemic agent (CHEBI:75835)
rifaximin (CHEBI:75246) has role anti-HIV agent (CHEBI:64946)
rifaximin (CHEBI:75246) has role antibacterial agent (CHEBI:33282)
rifaximin (CHEBI:75246) has role antiinfective agent (CHEBI:35441)
rifaximin (CHEBI:75246) has role antimicrobial agent (CHEBI:33281)
rifaximin (CHEBI:75246) has role antineoplastic agent (CHEBI:35610)
rifaximin (CHEBI:75246) has role antiparkinson drug (CHEBI:48407)
rifaximin (CHEBI:75246) has role antispasmodic drug (CHEBI:53784)
rifaximin (CHEBI:75246) has role antiviral agent (CHEBI:22587)
rifaximin (CHEBI:75246) has role cardiovascular drug (CHEBI:35554)
rifaximin (CHEBI:75246) has role gastrointestinal drug (CHEBI:55324)
rifaximin (CHEBI:75246) has role hepatoprotective agent (CHEBI:62868)
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
L-105ChEMBL
NSC-758957ChEMBL
Rifamycin L 105DrugBank
Rifamycin L 105SVDrugBank
RifaxidinDrugBank
Brand Names  Source
NormixChEMBL
RifacolChEMBL
TargaxanChEMBL
XifaxantaChEMBL
XifaxsanKEGG DRUG
Manual XrefsDatabases
2379DrugCentral
D02554KEGG DRUG
DB01220DrugBank
HMDB0015351HMDB
RifaximinWikipedia
Registry NumbersSources
Reaxys:7790802Reaxys
CAS:80621-81-4KEGG DRUG
CAS:80621-81-4ChemIDplus
Citations