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

Stem definitionDrug idCAS RN
4741 843663-66-1

Description:

MoleculeDescription

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:

DoseUnitRoute
86 mg O

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
Dec. 28, 2012 FDA JANSSEN THERAP
Jan. 19, 2018 PMDA Janssen Pharmaceutical KK

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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
Butterfly rash 46.24 31.38 12 3374 1761 63483875
Aspartate aminotransferase increased 45.48 31.38 38 3348 90239 63395397
Respiratory failure 43.48 31.38 39 3347 101819 63383817
Meningitis tuberculous 41.90 31.38 9 3377 584 63485052
Pyelonephritis chronic 36.98 31.38 7 3379 239 63485397
Disturbance in social behaviour 36.61 31.38 12 3374 3981 63481655
Herbal toxicity 34.33 31.38 5 3381 31 63485605
Cardiopulmonary failure 33.70 31.38 11 3375 3601 63482035
Hypomagnesaemia 32.96 31.38 20 3366 28717 63456919
Product use in unapproved indication 32.94 31.38 44 3342 179036 63306600
Deafness 32.90 31.38 17 3369 17940 63467696
Psychotic disorder 32.36 31.38 19 3367 25693 63459943
Gastroenteritis 31.77 31.38 19 3367 26571 63459065
Alanine aminotransferase increased 31.57 31.38 33 3353 103737 63381899
Hypokalaemia 31.56 31.38 33 3353 103771 63381865

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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
Polyneuropathy 45.97 31.96 25 3639 14871 34938396
Vomiting 43.48 31.96 86 3578 247535 34705732
Incorrect product administration duration 43.35 31.96 17 3647 4794 34948473
Drug-induced liver injury 39.69 31.96 29 3635 28803 34924464
Myelosuppression 35.03 31.96 23 3641 19242 34934025
Toxic optic neuropathy 32.64 31.96 9 3655 841 34952426
Psychotic disorder 32.31 31.96 24 3640 24428 34928839

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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
Drug-induced liver injury 84.71 31.42 59 6827 66058 79671444
Drug resistance 79.52 31.42 48 6838 42165 79695337
Incorrect product administration duration 72.01 31.42 30 6856 11992 79725510
Psychotic disorder 70.14 31.42 44 6842 41358 79696144
Tuberculosis 65.25 31.42 30 6856 15168 79722334
Myelosuppression 61.26 31.42 40 6846 40256 79697246
Meningitis tuberculous 59.68 31.42 15 6871 1190 79736312
Product use in unapproved indication 57.47 31.42 88 6798 250271 79487231
Alanine aminotransferase increased 53.54 31.42 68 6818 162502 79575000
Deafness 53.21 31.42 29 6857 21008 79716494
Respiratory failure 50.83 31.42 70 6816 180841 79556661
Hypokalaemia 50.21 31.42 62 6824 143978 79593524
Cardiopulmonary failure 47.67 31.42 19 6867 6782 79730720
Hepatitis toxic 41.80 31.42 16 6870 5131 79732371
Optic neuropathy 40.08 31.42 14 6872 3470 79734032
Pulmonary tuberculosis 38.44 31.42 17 6869 7848 79729654
Treatment noncompliance 37.23 31.42 33 6853 52235 79685267
Pain 36.76 31.42 8 6878 703794 79033708
Butterfly rash 36.66 31.42 11 6875 1685 79735817
Hypomagnesaemia 36.19 31.42 31 6855 46880 79690622
Pneumothorax 35.60 31.42 25 6861 28298 79709204
Drug ineffective 34.44 31.42 26 6860 1080887 78656615
Fatigue 32.75 31.42 20 6866 929707 78807795
Pyelonephritis chronic 32.44 31.42 7 6879 284 79737218
Blood sodium decreased 32.01 31.42 25 6861 33230 79704272
Toxic optic neuropathy 31.64 31.42 9 6877 1144 79736358
Electrolyte imbalance 31.43 31.42 24 6862 30857 79706645

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
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|

DiseaseRelationSNOMED_IDDOID
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 levelDissociation constantType (acidic/basic)
pKa1 11.93 acidic
pKa2 8.89 Basic
pKa3 2.19 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent 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 strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.43 CHEMBL
ATP synthase Enzyme INHIBITOR CHEMBL CHEMBL
ATP synthase subunit c Enzyme IC50 8.60 CHEMBL
ATP synthase subunit c Enzyme Kd 6.30 CHEMBL

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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