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bedaquiline 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	4741	843663-66-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: bedaquiline sirturo TMC207 bedaquiline fumarate	Bedaquiline is a diarylquinoline antimycobacterial drug that inhibits mycobacterial ATP (adenosine 5'-triphosphate) synthase, by binding to subunit c of the enzyme that is essential for the generation of energy in M. tuberculosis. Molecular weight: 555.52 Formula: C32H31BrN2O2 CLOGP: 7.25 LIPINSKI: 2 HAC: 4 HDO: 1 TPSA: 45.59 ALOGS: -6.46 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

bedaquiline
sirturo
TMC207
bedaquiline fumarate

Bedaquiline is a diarylquinoline antimycobacterial drug that inhibits mycobacterial ATP (adenosine 5'-triphosphate) synthase, by binding to subunit c of the enzyme that is essential for the generation of energy in M. tuberculosis.

Molecular weight: 555.52
Formula: C32H31BrN2O2
CLOGP: 7.25
LIPINSKI: 2
HAC: 4
HDO: 1
TPSA: 45.59
ALOGS: -6.46
ROTB: 8

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
86	mg	O

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
Dec. 28, 2012	FDA	JANSSEN THERAP
Jan. 19, 2018	PMDA	Janssen Pharmaceutical KK

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Electrocardiogram QT prolonged	458.24	31.38	156	3230	59374	63426262
Neuropathy peripheral	128.10	31.38	78	3308	113589	63372047
Hepatotoxicity	127.02	31.38	54	3332	36987	63448649
Anaemia	115.60	31.38	107	3279	293323	63192313
Off label use	90.65	31.38	142	3244	674320	62811316
Intentional product use issue	86.60	31.38	64	3322	127828	63357808
Drug-induced liver injury	59.49	31.38	33	3353	40189	63445447
Vomiting	55.23	31.38	103	3283	559514	62926122
Immune reconstitution inflammatory syndrome associated tuberculosis	52.32	31.38	10	3376	360	63485276
Polyneuropathy	49.04	31.38	21	3365	14568	63471068

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Electrocardiogram QT prolonged	709.24	31.96	233	3431	40719	34912548
Hepatotoxicity	451.41	31.96	142	3522	21343	34931924
Intentional product use issue	190.04	31.96	102	3562	59714	34893553
Neuropathy peripheral	178.89	31.96	110	3554	83153	34870114
Off label use	172.67	31.96	214	3450	419310	34533957
Anaemia	106.45	31.96	126	3538	233209	34720058
Optic neuritis	68.04	31.96	22	3642	3552	34949715
Drug resistance	62.49	31.96	37	3627	25890	34927377
Tuberculosis	59.11	31.96	25	3639	8552	34944715
Aspartate aminotransferase increased	49.13	31.96	47	3617	67736	34885531

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Electrocardiogram QT prolonged	1102.71	31.42	377	6509	90009	79647493
Hepatotoxicity	542.29	31.42	193	6693	51159	79686343
Neuropathy peripheral	297.17	31.42	172	6714	141133	79596369
Intentional product use issue	259.75	31.42	162	6724	151950	79585552
Off label use	250.09	31.42	345	6541	906870	78830632
Anaemia	211.85	31.42	224	6662	444791	79292711
Polyneuropathy	95.45	31.42	45	6841	24106	79713396
Aspartate aminotransferase increased	92.01	31.42	84	6802	138557	79598945
Vomiting	87.53	31.42	183	6703	665645	79071857
Optic neuritis	86.07	31.42	32	6854	9488	79728014

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J04AK05	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF TUBERCULOSIS Other drugs for treatment of tuberculosis
CHEBI has role	CHEBI:33231	antitubercular agents
FDA CS	M0582947	Diarylquinolines
FDA EPC	N0000186775	Diarylquinoline Antimycobacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000995	Antitubercular Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Pulmonary tuberculosis	indication	154283005	DOID:2957
Drug resistant tuberculosis	indication	423709000

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.93	acidic
pKa2	8.89	Basic
pKa3	2.19	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
EQ 100MG BASE	SIRTURO	JANSSEN THERAP	N204384	Dec. 28, 2012	RX	TABLET	ORAL	7498343	Dec. 1, 2026	TREATMENT OF PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS
EQ 100MG BASE	SIRTURO	JANSSEN THERAP	N204384	Dec. 28, 2012	RX	TABLET	ORAL	8546428	March 19, 2029	TREATMENT OF PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS
EQ 20MG BASE	SIRTURO	JANSSEN THERAP	N204384	May 27, 2020	RX	TABLET	ORAL	7498343	Dec. 1, 2026	TREATMENT OF PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS
EQ 20MG BASE	SIRTURO	JANSSEN THERAP	N204384	May 27, 2020	RX	TABLET	ORAL	8546428	March 19, 2029	TREATMENT OF PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 100MG BASE	SIRTURO	JANSSEN THERAP	N204384	Dec. 28, 2012	RX	TABLET	ORAL	Aug. 9, 2026	INDICATED AS PART OF COMBINATION THERAPY IN THE TREATMENT OF PEDIATRIC PATIENTS (12 TO LESS THAN 18 YEARS OF AGE AND WEIGHING AT LEAST 30 KG) WITH PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS
EQ 100MG BASE	SIRTURO	JANSSEN THERAP	N204384	Dec. 28, 2012	RX	TABLET	ORAL	May 27, 2027	INDICATED AS PART OF COMBINATION THERAPY IN THE TREATMENT OF PEDIATRIC PATIENTS 5 YEARS AND OLDER TO LESS THAN 12 YEARS OF AGE AND WEIGHING AT LEAST 15 KG WITH PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS (MDR-TB)
EQ 20MG BASE	SIRTURO	JANSSEN THERAP	N204384	May 27, 2020	RX	TABLET	ORAL	May 27, 2027	INDICATED AS PART OF COMBINATION THERAPY IN THE TREATMENT OF PEDIATRIC PATIENTS 5 YEARS AND OLDER TO LESS THAN 12 YEARS OF AGE AND WEIGHING AT LEAST 15 KG WITH PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS (MDR-TB)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	6.43	CHEMBL
ATP synthase	Enzyme		ATPL_MYCTU ATPB_MYCTU ATPA_MYCTU ATPG_MYCTU ATPE_MYCTU ATPFD_MYCTU ATPF_MYCTU ATP6_MYCTU	INHIBITOR			CHEMBL	CHEMBL
ATP synthase subunit c	Enzyme		Q5TIX5_MYCSM		IC50	8.60	CHEMBL
ATP synthase subunit c	Enzyme		ATPL_BACP3		Kd	6.30	CHEMBL

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External reference:

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ID	Source
BQ1	PDB_CHEM_ID
014821	NDDF
014822	NDDF
1010553003	SNOMEDCT_US
11171	IUPHAR_LIGAND_ID
1364503	RXNORM
196758	MMSL
29035	MMSL
30320	MMSL
4032353	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
SIRTURO	HUMAN PRESCRIPTION DRUG LABEL	1	59676-701	TABLET	100 mg	ORAL	NDA	35 sections
SIRTURO	HUMAN PRESCRIPTION DRUG LABEL	1	59676-702	TABLET	20 mg	ORAL	NDA	35 sections

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