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

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:46845 CHEBI:46845
CHEBI:46847 CHEBI:46847
ARO:3000157 ARO:3000157

Chemical structure

Computed structure properties
Molecular formula	C47H64N4O12
Charge	0
Average mass	877.045 Da
Monoisotopic mass	876.45207 Da
Source	ChEBI
InChIKey	WDZCUPBHRAEYDL-GZAUEHORSA-N

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

Equivalent identifiers for this same structure in other resources.

Activity roles

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

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:3000534`	rifapentine	`antibioticmech:aro-541de42362`	2026-08-30
CHEBI	`CHEBI:45304`	rifapentine	`antibioticmech:chebi-80097be7f3`	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:3000534 (rifapentine); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

14 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 6

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
Streptomyces venezuelae rox	ARO:3007209	not organism-specific	—	ARO:3007209 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000534 (rifapentine); database assertion, not a primary citation.)
iri	ARO:3002884	not organism-specific	—	ARO:3002884 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000534 (rifapentine); database assertion, not a primary citation.)
rgt1438	ARO:3002883	not organism-specific	—	ARO:3002883 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000534 (rifapentine); 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:3000534 (rifapentine); database assertion, not a primary citation.)
rphA	ARO:3000444	not organism-specific	—	ARO:3000444 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000534 (rifapentine); database assertion, not a primary citation.)
rphB	ARO:3003992	not organism-specific	—	ARO:3003992 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000534 (rifapentine); 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:3000534 (rifapentine); 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:3000534 (rifapentine); 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:3000534 (rifapentine); 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:3000534 (rifapentine); database assertion, not a primary citation.)
rpoB2	ARO:3000501	not organism-specific	—	ARO:3000501 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000534 (rifapentine); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 3

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:3000534 (rifapentine); database assertion, not a primary citation.)
RbpA	ARO:3000245	not organism-specific	—	ARO:3000245 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000534 (rifapentine); 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:3000534 (rifapentine); 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.