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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: ONP 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: ONP

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)

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	409.46	32.37	139	2603	51747	50550635
Hepatotoxicity	131.62	32.37	51	2691	27175	50575207
Neuropathy peripheral	120.05	32.37	71	2671	96686	50505696
Intentional product use issue	102.08	32.37	59	2683	76859	50525523
Anaemia	96.23	32.37	91	2651	252365	50350017
Off label use	95.42	32.37	122	2620	474304	50128078
Drug-induced liver injury	58.13	32.37	29	2713	28066	50574316
Vomiting	53.79	32.37	92	2650	460666	50141716
Polyneuropathy	45.64	32.37	19	2723	12112	50590270
Product use in unapproved indication	44.35	32.37	42	2700	115777	50486605
Meningitis tuberculous	42.62	32.37	9	2733	530	50601852
Respiratory failure	40.62	32.37	36	2706	91145	50511237
Aspartate aminotransferase increased	39.20	32.37	33	2709	77965	50524417
Hypokalaemia	35.76	32.37	33	2709	87959	50514423
Psychotic disorder	35.01	32.37	19	2723	21793	50580589
Herbal toxicity	34.25	32.37	5	2737	31	50602351
Hypomagnesaemia	33.95	32.37	19	2723	23137	50579245

FDA Adverse Event Reporting System (Male)

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	641.53	38.30	207	2753	35930	29535637
Hepatotoxicity	449.21	38.30	134	2826	17733	29553834
Intentional product use issue	218.38	38.30	99	2861	42399	29529168
Off label use	177.73	38.30	181	2779	300619	29270948
Neuropathy peripheral	170.30	38.30	99	2861	70928	29500639
Anaemia	79.97	38.30	99	2861	200852	29370715
Optic neuritis	55.40	38.30	18	2942	3091	29568476
Tuberculosis	47.26	38.30	20	2940	7176	29564391
Incorrect product administration duration	47.01	38.30	17	2943	4024	29567543
Drug-induced liver injury	40.86	38.30	26	2934	21629	29549938
Aspartate aminotransferase increased	40.31	38.30	39	2921	59686	29511881
Vomiting	38.81	38.30	73	2887	212187	29359380

FDA Adverse Event Reporting System (Geriatric)

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	983.90	33.45	336	5306	79112	64413978
Hepatotoxicity	543.70	33.45	182	5460	39780	64453310
Intentional product use issue	305.25	33.45	154	5488	95210	64397880
Neuropathy peripheral	280.44	33.45	156	5486	117369	64375721
Off label use	257.45	33.45	294	5348	632512	63860578
Anaemia	168.41	33.45	185	5457	378495	64114595
Drug-induced liver injury	86.16	33.45	53	5589	47590	64445500
Vomiting	82.50	33.45	161	5481	550956	63942134
Aspartate aminotransferase increased	77.59	33.45	72	5570	119716	64373374
Psychotic disorder	74.31	33.45	43	5599	34535	64458555
Polyneuropathy	71.89	33.45	35	5607	19859	64473231
Incorrect product administration duration	70.65	33.45	28	5614	9730	64483360
Optic neuritis	64.80	33.45	25	5617	8091	64484999
Product use in unapproved indication	64.09	33.45	78	5564	176540	64316550
Meningitis tuberculous	55.70	33.45	14	5628	1097	64491993
Deafness	53.71	33.45	28	5614	18331	64474759
Tuberculosis	53.38	33.45	25	5617	13013	64480077
Hypokalaemia	51.09	33.45	58	5584	121845	64371245
Drug resistance	50.91	33.45	34	5608	35068	64458022
Myelosuppression	49.50	33.45	29	5613	23801	64469289
Alanine aminotransferase increased	48.13	33.45	60	5582	138971	64354119
Respiratory failure	45.62	33.45	63	5579	161120	64331970
Drug ineffective	43.91	33.45	10	5632	840237	63652853
Treatment noncompliance	40.03	33.45	32	5610	43450	64449640
Cardiopulmonary failure	38.79	33.45	16	5626	6154	64486936
Hypomagnesaemia	37.63	33.45	29	5613	37347	64455743
Pulmonary tuberculosis	36.32	33.45	16	5626	7228	64485862
Blood sodium decreased	34.41	33.45	25	5617	29457	64463633
Optic neuropathy	34.10	33.45	12	5630	2999	64490091
Pneumothorax	33.94	33.45	23	5619	24275	64468815

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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

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

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

🐶 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)

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 20MG BASE	SIRTURO	JANSSEN THERAP	N204384	May 27, 2020	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	8546428	March 19, 2029	TREATMENT OF PULMONARY MULTI-DRUG RESISTANT TUBERCULOSIS

Orange Book exclusivity data (new drug applications)

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, 2022	NEW PATIENT POPULATION
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)

Bioactivity Summary:

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

External reference:

ID	Source
78846I289Y	UNII
D09872	KEGG_DRUG
4032353	VUID
N0000187065	NUI
845533-86-0	SECONDARY_CAS_RN
4032353	VANDF
C1664205	UMLSCUI
CHEBI:72292	CHEBI
BQ1	PDB_CHEM_ID
CHEMBL376488	ChEMBL_ID
5388906	PUBCHEM_CID
DB08903	DRUGBANK_ID
CHEMBL2105700	ChEMBL_ID
9316	INN_ID
C493870	MESH_SUPPLEMENTAL_RECORD_UI
11171	IUPHAR_LIGAND_ID
1364503	RXNORM
196758	MMSL
29035	MMSL
30320	MMSL
d07941	MMSL
014821	NDDF
014822	NDDF
1010553003	SNOMEDCT_US
714086004	SNOMEDCT_US
714087008	SNOMEDCT_US

Pharmaceutical products:

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