rifapentine

CHEBI:45304 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

Rifapentine is a semisynthetic rifamycin that inhibits DNA-dependent RNA synthesis. It is often used in the treatment of tuberculosis and leprosy. — PMID:15700959

Classification

rifamycin antibioticARO:3000157

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:26580
• Label unavailable CHEBI:46845
• Label unavailable CHEBI:46847
• 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(C6CCCC6)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/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1

Also called

• (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-{(E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl}-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-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-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin (EXACT_SYNONYM)— chebi
• Cyclopentylrifampicin (EXACT_SYNONYM)— chebi
• Priftin (TN) (EXACT_SYNONYM)— chebi
• Rifapentine (EXACT_SYNONYM)— chebi
• priftin (EXACT_SYNONYM)— aro

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.

• rifapentineARO:3000534
• cas:61379-65-5
• kegg.compound:C08059
• chembl:CHEMBL1660
• pubchem.compound:135403821

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:DB01201
• kegg.drug:D00879

Patents and articles

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

• wikipedia.en:Rifapentine

Activity roles

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

• 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:3000534 (rifapentine); database assertion, not a primary citation.)

Mechanism summary

Clinical status

APPROVED

Resistance mechanisms

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

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. 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).

Explore across X-Mech: MediaIngredientMech (rifapentine) · CultureMech · NaturalProductMech · PathwayMech · TraitMech