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

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

diarylquinoline antibioticARO:3004491

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:25477
Label unavailable CHEBI:26513
Label unavailable CHEBI:26878
Label unavailable CHEBI:35618
Label unavailable CHEBI:37141
Label unavailable CHEBI:50996
diarylquinoline antibiotic 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

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.

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.

Patents and articles

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

Activity roles

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

antitubercular agent 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.

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

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

Observations 1–20 of 284

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; not specified	—	10 source isolates 10 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	INTERMEDIATE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; solid media	—	7 source isolates 7 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	79 source isolates 79 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2023; solid media	—	5 source isolates 5 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; solid media	—	5 source isolates 5 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.03 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	1704 source isolates 1704 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.03 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	227 source isolates 227 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.03 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	378 source isolates 378 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.06 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	1795 source isolates 1795 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.06 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	117 source isolates 117 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.06 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	371 source isolates 371 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	383 source isolates 383 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	42 source isolates 42 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	81 source isolates 81 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	77 source isolates 77 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	13 source isolates 13 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	7 source isolates 7 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.5 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	32 source isolates 32 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	0.5 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 0.25 mg/L	—	3 source isolates 3 measurements	Evidence Page data (JSON.gz)

Resistance mechanisms

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

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

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 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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.
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.

Provenance

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

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