BEDAQUILINE

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

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 of BEDAQUILINE

Structure Search

SMILES

COC1=NC2=CC=C(Br)C=C2C=C1[C@@H](C3=CC=CC=C3)[C@@](O)(CCN(C)C)C4=CC=CC5=CC=CC=C45

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

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:23:58 UTC 2023` Edited by `admin` on `Fri Dec 15 16:23:58 UTC 2023`
Record UNII	78846I289Y
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BEDAQUILINE

Official 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

R-207910

Code

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

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

NDF-RT

N0000186775

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

WHO-VATC

QJ04AK05

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

NCI_THESAURUS

C280

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

WHO-ATC

J04AK05

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

FDA ORPHAN DRUG

199304

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

LIVERTOX

NBK548859

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

Code System Code Type Description

ChEMBL

CHEMBL376488

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

USAN

XX-135

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

SMS_ID

100000126166

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

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DAILYMED

78846I289Y

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

MERCK INDEX

m2288

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

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Merck Index

EPA CompTox

DTXSID80903989

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

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WIKIPEDIA

Bedaquiline

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

EVMPD

SUB32824

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

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DRUG BANK

DB08903

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

PUBCHEM

5388906

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

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DRUG CENTRAL

4741

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

NCI_THESAURUS

C87658

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

RXCUI

1364504

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

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RxNorm

HSDB

8217

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

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EU-Orphan Drug

EU/3/05/314 POSITIVE

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

On 26 August 2005, orphan designation (EU/3/05/314) was granted by the European Commission to Tibotec Pharmaceuticals Ltd., Ireland, for (1R,2S) 6-bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-(1-naphthyl)-beta-phenyl-3-quinolineethanol for the treatment of tuberculosis.

LACTMED

Bedaquiline

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

CHEBI

72292

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

NDF-RT

N0000186774

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

Diarylquinolines [Chemical/Ingredient]

INN

9316

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

CAS

843663-66-1

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

FDA UNII

78846I289Y

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

MESH

C493870

Created by admin on Fri Dec 15 16:23:58 UTC 2023 , Edited by admin on Fri Dec 15 16:23:58 UTC 2023

PRIMARY

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Qualification:

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Amount:


					78846I289Y

EXCRETED UNCHANGED

Qualification:

FECAL

Amount:


					P04QX2C1A5

BEDAQUILINE FUMARATE

SALT/SOLVATE -> PARENT


					R0EM8D5HFD

MYCOBACTERIUM TUBERCULOSIS

TARGET ORGANISM->INHIBITOR


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

Related Record Type Details


					W96L2O9I1E

N-MONODESMETHYL BEDAQUILINE

METABOLITE LESS ACTIVE -> PARENT

Comments:

CYP3A4 METABOLITE; 4-5 TIMES LESS ACTIVE; RESPONSIBLE FOR QT PROLONGATION DUE TO LONG TERMINAL HALF LIFE

Interaction Type:

MAJOR

Qualification:

FECAL

Amount:

Related Record Type Details


					78846I289Y

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC

Volume of Distribution	PHARMACOKINETIC