BEDAQUILINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H31BrN2O2
Molecular Weight	555.505
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=NC2=CC=C(Br)C=C2C=C1[C@@H](C3=CC=CC=C3)[C@@](O)(CCN(C)C)C4=C5C=CC=CC5=CC=C4

InChI

InChIKey=QUIJNHUBAXPXFS-XLJNKUFUSA-N

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

HIDE SMILES / InChI

Molecular Formula	C32H31BrN2O2
Molecular Weight	555.505
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204384s006lbl.pdf

Bedaquiline (trade name Sirturo, code names TMC207 and R207910) is a diarylquinoline anti-tuberculosis drug, which was discovered by a team led by Koen Andries at Janssen Pharmaceutica. When it was approved by the FDA on the 28th December 2012, it was the first new medicine to fight TB in more than forty years, and is specifically approved to treat multi-drug-resistant tuberculosis. Bedaquiline is a diarylquinoline antimycobacterial drug that inhibits the proton pump of mycobacterial ATP (adenosine 5'-triphosphate) synthase, an enzyme that is essential for the generation of energy in Mycobacterium tuberculosis. Bacterial death occurs as a result of bedaquiline.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
ATP synthase subunit c 2 Target ID: P9WPS0 Gene ID: NA Gene Symbol: atpE Target Organism: Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh) Sources: http://www.ncbi.nlm.nih.gov/pubmed/17496888	Inhibitor 8504
ATP synthase subunit c 2 Target ID: P9WPS1 Gene ID: 886937.0 Gene Symbol: atpE Target Organism: Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Sources: http://www.ncbi.nlm.nih.gov/pubmed/17496888	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis, multidrug-resistant 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204384s006lbl.pdf	Curative		Approved 8583	SIRTURO Approved Use Indicated as part of combination therapy in the treatment of adults (18 years and older) with pulmonary multi-drug resistant tuberculosis (MDR-TB). Reserve SIRTURO for use when an effective treatment regimen cannot otherwise be provided. Administer SIRTURO by directly observed therapy (DOT). This indication is approved under accelerated approval based on time to sputum culture conversion Launch Date 2012

C_max

Value	Dose	Co-administered	Analyte	Population
3.755 mg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered:		BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.547 mg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
64.53 mg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered:		BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
38.737 mg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
24 h REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered:		BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
24 h REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Analyte	Population
0.01% REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered:	BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.01% REVIEW https://pubmed.ncbi.nlm.nih.gov/24860154/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	BEDAQUILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.01% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf	400 mg 1 times / day unknown, oral dose: 400 mg route of administration: Oral experiment type: UNKNOWN co-administered:	BEDAQUILINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
400 mg 4 times / week multiple, oral Overdose Dose: 400 mg, 4 times / week Route: oral Route: multiple Dose: 400 mg, 4 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/30951878	unhealthy, 21 years Health Status: unhealthy Age Group: 21 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/30951878	Sources: https://pubmed.ncbi.nlm.nih.gov/30951878
400 \| 200 mg\|mg 1\|3 times / day\|week multiple, oral Recommended Dose: 400 \| 200 mg\|mg, 1\|3 times / day\|week Route: oral Route: multiple Dose: 400 \| 200 mg\|mg, 1\|3 times / day\|week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf	unhealthy, 34 years Health Status: unhealthy Age Group: 34 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf	Other AEs: Death... Other AEs: Death (11.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf

AEs

AE	Significance	Dose	Population
Death	11.4%	400 \| 200 mg\|mg 1\|3 times / day\|week multiple, oral Recommended Dose: 400 \| 200 mg\|mg, 1\|3 times / day\|week Route: oral Route: multiple Dose: 400 \| 200 mg\|mg, 1\|3 times / day\|week Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf	unhealthy, 34 years Health Status: unhealthy Age Group: 34 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	inhibitor 2438 inducer 440	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP3A4/5 296 CYP4A 20 P-gp 1741	P-gp 2052	CYP1A2 832 CYP2C19 329

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
CYP4A 34	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 8.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/204384Orig1s000ClinPharmR.pdf Page: 23.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 5.0	major		yes (co-administration study) Comment: ketoconazole increased bedaquiline exposure 22%, rifampin decreased bedaquiline exposure 52% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/204384s000lbl.pdf Page: 5.0
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/204384Orig1s000ClinPharmR.pdf Page: 2.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/204384Orig1s000SumR.pdf Page: 5.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:72292	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72292
MolPort	MolPort-035-683-920	https://www.molport.com/shop/molecule-link/MolPort-035-683-920
ZINC	ZINC000004655029	http://zinc15.docking.org/substances/ZINC000004655029

PubMed

Title	Date	PubMed
Efflux inhibition with verapamil potentiates bedaquiline in Mycobacterium tuberculosis.	2014	24126586
Short-course chemotherapy with TMC207 and rifapentine in a murine model of latent tuberculosis infection.	2011-09-15	21659613
Bactericidal activity of the diarylquinoline TMC207 against Mycobacterium tuberculosis outside and within cells.	2010-09	20732832
In vitro interactions between new antitubercular drug candidates SQ109 and TMC207.	2010-07	20385864
TMC207: the first compound of a new class of potent anti-tuberculosis drugs.	2010-06	20521931
In vitro antimycobacterial spectrum of a diarylquinoline ATP synthase inhibitor.	2007-11	17709466
New drugs being developed for the treatment of tuberculosis.	2005-07	16022581
New small-molecule synthetic antimycobacterials.	2005-06	15917508

Patents

Sample Use Guides

In Vivo Use Guide

400 mg once daily for 2 weeks followed by 200 mg 3 times per week for 22 weeks with food. Swallow SIRTURO (bedaquiline) tablets whole with water.

Route of Administration: Oral

In Vitro Use Guide

Modification of the atpE target gene, and/or upregulation of the MmpS5-MmpL5 efflux pump have been associated with increased bedaquiline MIC values in isolates of M. tuberculosis. Target-based mutations generated in preclinical studies lead to 8- to 133-fold increases in bedaquiline MIC, resulting in MICs ranging from 0.25 to 4.0 ug/mL. Efflux-based mutations have been seen in preclinical and clinical isolates. These lead to 2- to 8-fold increases in bedaquiline MICs, resulting in bedaquiline MICs ranging from 0.25 to 0.50 ug/ mL.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:26:47 GMT 2025` Edited by `admin` on `Mon Mar 31 18:26:47 GMT 2025`
Record UNII	78846I289Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BEDAQUILINE

Official Name

English

R-207910

Preferred Name

English

bedaquiline [INN]

Common Name

English

(1R,2S) 6-BROMO-ALPHA-(2-(DIMETHYLAMINO)ETHYL)-2-METHOXY-ALPHA-(1-NAPHTHYL)-BETA-PHENYL-3-QUINOLINEETHANOL

Systematic Name

English

BEDAQUILINE [VANDF]

Common Name

English

TMC207

Code

English

BEDAQUILINE [USAN]

Common Name

English

(1R,2S)-1-(6-BROMO-2-METHOXYQUINOLIN-3-YL)-4-(DIMETHYLAMINO)-2-(NAPHTHALEN-1-YL)-1- PHENYLBUTAN-2-OL

Systematic Name

English

3-QUINOLINEETHANOL, 6-BROMO-.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)-2-METHOXY-.ALPHA.-1-NAPHTHALENYL-.BETA.-PHENYL-, (.ALPHA.S,.BETA.R)-

Common Name

English

TMC-207

Code

English

BEDAQUILINE [MI]

Common Name

English

R207910

Code

English

Bedaquiline [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

589917