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: ONP

  • 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 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 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 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 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 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:

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, 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:

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