rifabutin

CHEBI:45367 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Rifabutin is a semisynthetic rifamycin used in tuberculosis therapy. It inhibits DNA-dependent RNA synthesis. — PMID:15700959

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.

rifamycin antibiotic ARO:3000157

Chemical structure

Computed structure properties
Molecular formula	C46H62N4O11
Charge	0
Average mass	847.019 Da
Monoisotopic mass	846.44151 Da
Source	ChEBI
InChIKey	ATEBXHFBFRCZMA-VXTBVIBXSA-N

SMILES

CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C2=NC3(CCN(CC(C)C)CC3)NC2=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)C4=O

InChI

InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1

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.

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:3000530`	rifabutin	`antibioticmech:aro-091952d65e`	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:3000530 (rifabutin); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

268 observations · Browse all observations · Complete record (JSON.gz)

Observations 1–20 of 268

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	118 source isolates 118 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	69 source isolates 69 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; not specified	—	3 source isolates 3 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; not specified	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	INTERMEDIATE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; solid media	—	8 source isolates 8 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	7 source isolates 7 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2023; not specified	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	249 source isolates 249 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	63 source isolates 63 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	45 source isolates 45 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	147 source isolates 147 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	31 source isolates 31 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	18 source isolates 18 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.5 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	106 source isolates 106 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.5 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	30 source isolates 30 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.5 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	15 source isolates 15 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	1.0 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	162 source isolates 162 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	1.0 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	41 source isolates 41 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	1.0 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.12 mg/L	—	33 source isolates 33 measurements	Evidence Page data (JSON.gz)

Resistance mechanisms

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

ANTIBIOTIC_INACTIVATION 5

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
iri	ARO:3002884	not organism-specific	—	ARO:3002884 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); database assertion, not a primary citation.)
rgt1438	ARO:3002883	not organism-specific	—	ARO:3002883 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); 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:3000530 (rifabutin); database assertion, not a primary citation.)
rphA	ARO:3000444	not organism-specific	—	ARO:3000444 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); database assertion, not a primary citation.)
rphB	ARO:3003992	not organism-specific	—	ARO:3003992 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_REPLACEMENT 5

ANTIBIOTIC_TARGET_REPLACEMENT
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli rpoB mutants conferring resistance to rifampicin	ARO:3003288	not organism-specific	—	ARO:3003288 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); 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:3000530 (rifabutin); 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:3000530 (rifabutin); 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:3000530 (rifabutin); database assertion, not a primary citation.)
rpoB2	ARO:3000501	not organism-specific	—	ARO:3000501 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); 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:3000530 (rifabutin); database assertion, not a primary citation.)
HelR	ARO:3007208	not organism-specific	—	ARO:3007208 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); database assertion, not a primary citation.)
RbpA	ARO:3000245	not organism-specific	—	ARO:3000245 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); 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:3000530 (rifabutin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 3

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium tuberculosis ponA1 mutations conferring resistance to rifabutin	ARO:3004960	not organism-specific	—	ARO:3004960 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); database assertion, not a primary citation.)
Mycobacterium tuberculosis rpoC mutations confer resistance to rifampicin	ARO:3004994	not organism-specific	—	ARO:3004994 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); database assertion, not a primary citation.)
rifampicin resistant rpoC	ARO:3004995	not organism-specific	—	ARO:3004995 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000530 (rifabutin); 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 2026-09-26 · seed_from_sources
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
RESEEDED_FROM_SOURCES 2026-10-05 · seed_from_sources
Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

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