AntibioticMech

bedaquiline

CHEBI:72292 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

A quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria. — ChEBI

Classification

diarylquinoline antibioticARO:3004491

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:25477 CHEBI:25477
• CHEBI:26513 CHEBI:26513
• CHEBI:26878 CHEBI:26878
• CHEBI:35618 CHEBI:35618
• CHEBI:37141 CHEBI:37141
• CHEBI:50996 CHEBI:50996
• ARO:3004491 ARO:3004491

Chemical structure

Computed structure properties

Molecular formula	C32H31BrN2O2
Charge	0
Average mass	555.516 Da
Monoisotopic mass	554.15689 Da
Source	ChEBI
InChIKey	QUIJNHUBAXPXFS-XLJNKUFUSA-N

SMILES

COc1nc2ccc(Br)cc2cc1[C@@H](c1ccccc1)[C@@](O)(CCN(C)C)c1cccc2ccccc12

InChI

InChI=1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1

Also called

• bedaquilina (INN)— chebi
• bedaquilinum (INN)— chebi
• bédaquiline (INN)— chebi
• (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol (EXACT_SYNONYM)— chebi
• 1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol (EXACT_SYNONYM)— chebi
• R 207910 (EXACT_SYNONYM)— chebi
• R207910 (EXACT_SYNONYM)— chebi
• TMC 207 (EXACT_SYNONYM)— chebi
• TMC-207 (EXACT_SYNONYM)— chebi
• TMC207 (EXACT_SYNONYM)— chebi
• Sirturo (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3004492
• cas:654653-93-7
• cas:843663-66-1
• drugbank:DB08903
• drugcentral:4741
• kegg.drug:D09872
• patent:WO2005117875
• patent:WO2006067048
• pdb-ccd:BQ1
• reaxys:10733008
• wikipedia.en:Bedaquiline
• chembl:CHEMBL376488
• pubchem.compound:5388906

Activity roles

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

• CHEBI:33231 CHEBI:33231

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:3004492	bedaquiline	antibioticmech:aro-147ef273d9	2026-08-30
CHEBI	CHEBI:72292	bedaquiline	antibioticmech:chebi-9b38ad9d40	2026-08-30

Mechanism summary

Mode of action

ENERGY_METABOLISM_INHIBITION host shared target — Assigned from ChEBI role CHEBI:20854 (ATP synthase inhibitor). ChEBI asserts the role on the compound. 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.

Resistance mechanisms

4 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_TARGET_ALTERATION 4

ANTIBIOTIC_TARGET_ALTERATION

Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium abscessus atpE with mutation conferring resistance to bedaquiline	ARO:3007476	not organism-specific	—	ARO:3007476 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004492 (bedaquiline); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv0678 with mutation conferring resistance to bedaquiline	ARO:3007674	not organism-specific	—	ARO:3007674 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004492 (bedaquiline); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv2535c with mutation conferring resistance to bedaquiline	ARO:3007692	not organism-specific	—	ARO:3007692 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004492 (bedaquiline); database assertion, not a primary citation.)
Mycobacterium tuberculosis atpE with mutation conferring resistance to bedaquiline	ARO:3007854	not organism-specific	—	ARO:3007854 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004492 (bedaquiline); database assertion, not a primary citation.)

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

Provenance

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