rifampicin

CHEBI:28077 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

A member of the class of rifamycins that is a a semisynthetic antibiotic derived from Amycolatopsis rifamycinica (previously known as Amycolatopsis mediterranei and Streptomyces mediterranei). — 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:26580 CHEBI:26580
CHEBI:38532 CHEBI:38532
CHEBI:46847 CHEBI:46847
CHEBI:46920 CHEBI:46920
CHEBI:59779 CHEBI:59779
CHEBI:72588 CHEBI:72588
ARO:3000157 ARO:3000157

Chemical structure

Computed structure properties
Molecular formula	C43H58N4O12
Charge	0
Average mass	822.953 Da
Monoisotopic mass	822.40512 Da
Source	ChEBI
InChIKey	JQXXHWHPUNPDRT-WLSIYKJHSA-N

SMILES

CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(/C=N/N5CCN(C)CC5)c(O)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/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1

Also called

rifampicina (INN)— chebi
rifampicinum (INN)— chebi
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate (EXACT_SYNONYM)— chebi
3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV (EXACT_SYNONYM)— chebi
RFP (EXACT_SYNONYM)— chebi
Rifampicin (EXACT_SYNONYM)— chebi
Rifampin (EXACT_SYNONYM)— chebi
rifamcin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000169
cas:13292-46-1
drugbank:DB01045
hmdb:HMDB0015179
kegg.compound:C06688
kegg.drug:D00211
patent:NL6509961
patent:US3342810
pdb-ccd:RFP
reaxys:5723476
wikipedia.en:Rifampicin
chembl:CHEMBL374478
pubchem.compound:135398735

Activity roles

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

CHEBI:33231 CHEBI:33231
CHEBI:35816 CHEBI:35816

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:3000169`	rifampin	`antibioticmech:aro-9e3beda439`	2026-08-30
CHEBI	`CHEBI:28077`	rifampicin	`antibioticmech:chebi-8bf7b5d163`	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:3000169 (rifampin); database assertion, not a primary citation.)

Mechanism summary

Mode of action: MULTIPLE host shared target — Assigned from ChEBI roles CHEBI:37416 (EC 2.7.7.6 (RNA polymerase) inhibitor), CHEBI:48001 (protein synthesis inhibitor), CHEBI:59517 (DNA synthesis inhibitor), which map to NUCLEIC_ACID_SYNTHESIS_INHIBITION, PROTEIN_SYNTHESIS_INHIBITION. ChEBI asserts these roles on the compound; a curator should decide whether one is primary. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.
Clinical status: APPROVED

Resistance mechanisms

40 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 14

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
Nocardia farcinica rox	ARO:3007210	not organism-specific	—	ARO:3007210 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
Streptomyces venezuelae rox	ARO:3007209	not organism-specific	—	ARO:3007209 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
arr-1	ARO:3002846	not organism-specific	—	ARO:3002846 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
arr-2	ARO:3002847	not organism-specific	—	ARO:3002847 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
arr-3	ARO:3002848	not organism-specific	—	ARO:3002848 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
arr-4	ARO:3002849	not organism-specific	—	ARO:3002849 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
arr-5	ARO:3002850	not organism-specific	—	ARO:3002850 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
arr-7	ARO:3002852	not organism-specific	—	ARO:3002852 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
arr-8	ARO:3002853	not organism-specific	—	ARO:3002853 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
iri	ARO:3002884	not organism-specific	—	ARO:3002884 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
rgt1438	ARO:3002883	not organism-specific	—	ARO:3002883 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); 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:3000169 (rifampin); database assertion, not a primary citation.)
rphA	ARO:3000444	not organism-specific	—	ARO:3000444 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
rphB	ARO:3003992	not organism-specific	—	ARO:3003992 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_REPLACEMENT 10

ANTIBIOTIC_TARGET_REPLACEMENT
Determinant	ARO ID	Organism	Gene families	Evidence
Bacillus subtilis rpoB mutants conferring resistance to rifampin	ARO:3007073	not organism-specific	—	ARO:3007073 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
Bifidobacterium adolescentis rpoB mutants conferring resistance to rifampicin	ARO:3004480	not organism-specific	—	ARO:3004480 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
Clostridioides difficile rpoB with mutation conferring resistance to rifampicin	ARO:3004563	not organism-specific	—	ARO:3004563 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); 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:3000169 (rifampin); database assertion, not a primary citation.)
Helicobacter pylori rpoB mutation conferring resistance to rifampicin	ARO:3007051	not organism-specific	—	ARO:3007051 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); 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:3000169 (rifampin); 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:3000169 (rifampin); 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:3000169 (rifampin); database assertion, not a primary citation.)
Vibrio vulnificus rpoB mutants conferring resistance to rifampin	ARO:3007794	not organism-specific	—	ARO:3007794 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
rpoB2	ARO:3000501	not organism-specific	—	ARO:3000501 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 6

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
AcrAB-TolC	ARO:3000384	not organism-specific	—	ARO:3000384 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
AdeIJK	ARO:3000772	not organism-specific	—	ARO:3000772 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
EfrAB	ARO:3003947	not organism-specific	—	ARO:3003947 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnEF	ARO:3004585	not organism-specific	—	ARO:3004585 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
LptD	ARO:3005059	not organism-specific	—	ARO:3005059 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
efpA	ARO:3003955	not organism-specific	—	ARO:3003955 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 6

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium tuberculosis embB with mutation conferring resistance to rifampicin	ARO:3003465	not organism-specific	—	ARO:3003465 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
Mycobacterium tuberculosis ponA1 mutations conferring resistance to rifabutin	ARO:3004960	not organism-specific	—	ARO:3004960 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
Mycobacterium tuberculosis rpoA mutations confer resistance to rifampicin	ARO:3004999	not organism-specific	—	ARO:3004999 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); 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:3000169 (rifampin); database assertion, not a primary citation.)
rifampicin resistant rpoA	ARO:3004998	not organism-specific	—	ARO:3004998 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
rifampicin resistant rpoC	ARO:3004995	not organism-specific	—	ARO:3004995 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); 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:3000169 (rifampin); database assertion, not a primary citation.)
HelR	ARO:3007208	not organism-specific	—	ARO:3007208 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); database assertion, not a primary citation.)
RbpA	ARO:3000245	not organism-specific	—	ARO:3000245 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000169 (rifampin); 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:3000169 (rifampin); 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.