rifaximin

CHEBI:75246 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

rifamycin antibioticARO:3000157

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:24995 CHEBI:24995
CHEBI:26580 CHEBI:26580
CHEBI:47622 CHEBI:47622
CHEBI:51026 CHEBI:51026
CHEBI:51914 CHEBI:51914
CHEBI:59779 CHEBI:59779
CHEBI:72588 CHEBI:72588
ARO:3000157 ARO:3000157

Chemical structure

Computed structure properties
Molecular formula	C43H51N3O11
Charge	0
Average mass	785.891 Da
Monoisotopic mass	785.35236 Da
Source	ChEBI
InChIKey	NZCRJKRKKOLAOJ-XRCRFVBUSA-N

SMILES

CO[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

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

Also called

Xifaxsan (BRAND_NAME)— chebi
rifaximina (INN)— chebi
rifaximine (INN)— chebi
rifaximinun (INN)— chebi
(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 (EXACT_SYNONYM)— chebi
Rifamycin L 105 (EXACT_SYNONYM)— chebi
Rifamycin L 105SV (EXACT_SYNONYM)— chebi
Rifaxidin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000517
cas:80621-81-4
drugbank:DB01220
drugcentral:2379
hmdb:HMDB0015351
kegg.drug:D02554
reaxys:7790802
wikipedia.en:Rifaximin
chembl:CHEMBL1617
pubchem.compound:6436173

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3000517`	rifaximin	`antibioticmech:aro-f950f96b1f`	2026-08-30
CHEBI	`CHEBI:75246`	rifaximin	`antibioticmech:chebi-ca0ee79f16`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

rifamycin sensitive beta-subunit of RNA polymerase (rpoB) PROTEIN_COMPLEX DIRECT_BINDING_TARGET

ARO:3000737

CARD/ARO database assertion; target organism, strain, and assay are not specified. RpoB is asserted as a target in the RNA polymerase complex. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000737 (CARD/ARO asserts targeted_by_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

16 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_INACTIVATION 6

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
Streptomyces venezuelae rox	ARO:3007209	not organism-specific	—	ARO:3007209 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
iri	ARO:3002884	not organism-specific	—	ARO:3002884 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
rgt1438	ARO:3002883	not organism-specific	—	ARO:3002883 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
rifampin ADP-ribosyltransferase (Arr)	ARO:3000390	not organism-specific	—	ARO:3000390 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
rphA	ARO:3000444	not organism-specific	—	ARO:3000444 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
rphB	ARO:3003992	not organism-specific	—	ARO:3003992 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_REPLACEMENT 6

ANTIBIOTIC_TARGET_REPLACEMENT
Determinant	ARO ID	Organism	Gene families	Evidence
Clostridioides difficile rpoB with mutation conferring resistance to rifampicin	ARO:3004563	not organism-specific	—	ARO:3004563 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
Escherichia coli rpoB mutants conferring resistance to rifampicin	ARO:3003288	not organism-specific	—	ARO:3003288 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
Mycobacterium leprae rpoB mutations conferring resistance to rifampicin	ARO:3003284	not organism-specific	—	ARO:3003284 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
Mycobacterium tuberculosis rpoB with mutations conferring resistance to rifampicin	ARO:3003283	not organism-specific	—	ARO:3003283 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
Staphylococcus aureus rpoB mutants conferring resistance to rifampicin	ARO:3003285	not organism-specific	—	ARO:3003285 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
rpoB2	ARO:3000501	not organism-specific	—	ARO:3000501 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 4

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
DnaA	ARO:3000248	not organism-specific	—	ARO:3000248 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
HelR	ARO:3007208	not organism-specific	—	ARO:3007208 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
RbpA	ARO:3000245	not organism-specific	—	ARO:3000245 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)
sigma factor conferring resistance to rifampin	ARO:3000261	not organism-specific	—	ARO:3000261 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000517 (rifaximin); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.