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.

Label unavailable CHEBI:24995
Label unavailable CHEBI:26580
Label unavailable CHEBI:47622
Label unavailable CHEBI:51026
Label unavailable CHEBI:51914
Label unavailable CHEBI:59779
Label unavailable CHEBI:72588
rifamycin antibiotic 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Rifaximin

Activity roles

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

antimicrobial agent 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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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