rifampicin

CHEBI:28077 ·resolve ·ANTIMYCOBACTERIAL ·EXACT REVIEWED

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

Classification

rifamycin antibioticARO:3000157

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:26580
• Label unavailable CHEBI:38532
• Label unavailable CHEBI:46847
• Label unavailable CHEBI:46920
• Label unavailable CHEBI:59779
• Label unavailable CHEBI:72588
• rifamycin antibiotic ARO:3000157

Chemical structure

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

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.

• rifampinARO:3000169
• cas:13292-46-1
• hmdb:HMDB0015179
• kegg.compound:C06688
• pdb-ccd:RFP
• reaxys:5723476
• chembl:CHEMBL374478
• pubchem.compound:135398735

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.

• drugbank:DB01045
• kegg.drug:D00211

Patents and articles

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

• patent:NL6509961
• patent:US3342810
• wikipedia.en:Rifampicin

Activity roles

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

• antitubercular agent CHEBI:33231
• leprostatic drug 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.

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.)

bacterial RNA polymerase beta-subunit channel PROTEIN_COMPLEX DIRECT_BINDING_TARGET

A T. aquaticus core-RNAP cocrystal directly localized rifampicin in the beta-subunit DNA/RNA channel, where biochemical results support steric occlusion of transcripts after two to three nucleotides. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2001-03 (retrieved 2026-09-02).

Thermus aquaticus NCBITaxon:271

• PMID:11290327 (Primary rifampicin-bound bacterial RNAP structural mechanism study (DOI:10.1016/S0092-8674(01)00286-0).)

Mechanism summary

Mode of action

NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:11290327 resolved rifampicin bound to Thermus aquaticus core RNA polymerase. It occupies a beta-subunit pocket in the DNA/RNA channel more than 12 angstrom from the active site and sterically blocks extension once nascent RNA reaches two to three nucleotides. This primary transcription mechanism replaces the source-seeded MULTIPLE bucket.

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.

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

Observations 1–20 of 363

Resistance mechanisms

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

Record-level evidence

• PMID:11290327 (Primary exact-rifampicin bacterial RNA-polymerase cocrystal and biochemical study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

7. REVIEWED 2026-09-03 · codex · LLM-assisted

   Verified exact ChEBI/CARD rifampicin/rifampin identity, structure, roles, antimycobacterial class, FDA provenance, and retained CARD assertions; replaced the ambiguous seeded MULTIPLE mode with transcription inhibition and added the directly bound RNAP complex.

8. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

9. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank rifampin-resistant Enterococcus faecium isolate MIC observation.

10. CURATED_RESISTANT_TAXA 2026-09-19 · codex · LLM-assisted

    Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 rifampicin-resistant Enterococcus faecium MIC observation for AR-0500; preserved source Blood, BioSample SAMN11953784, and Study ID NEW-13 in evidence notes.

11. STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted

    Structured BioSample accessions on 2 activity_spectrum observation(s) where evidence notes already named exactly one accession.

12. 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.

13. 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.

14. CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted

    Added curated Thermus aquaticus RpoB (Q9KWU6) and M. tuberculosis H37Rv RpoB (P9WGY9) UniProtKB protein examples on the PRIMARY_LITERATURE bacterial RNA polymerase beta-subunit channel molecular target.

Provenance

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

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