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.
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
Equivalent identifiers for this same structure in other resources.
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
Resistance mechanisms
17 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 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
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.