rifapentine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, rifamycin derivatives 2378 61379-65-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • rifapentine
  • DL473
Rifapentine, a cyclopentyl rifamycin, inhibits DNA-dependent RNA polymerase in susceptible strains of Mycobacterium tuberculosis but does not affect mammalian cells at concentrations that are active against these bacteria. At therapeutic levels, rifapentine inhibits RNA transcription by preventing the initiation of RNA chain formation. It forms a stable complex with bacterial DNA-dependent RNA polymerase, leading to repression of RNA synthesis and cell death. Rifapentine and its 25-desacetyl metabolite accumulate in human monocyte-derived macrophages and are bactericidal to both intracellular and extracellular M. tuberculosis bacilli.
  • Molecular weight: 877.05
  • Formula: C47H64N4O12
  • CLOGP: 5.09
  • LIPINSKI: 4
  • HAC: 16
  • HDO: 6
  • TPSA: 220.15
  • ALOGS: -4.61
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.11 g O

ADMET properties:

PropertyValueReference
BA (Bioavailability) 70 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
June 22, 1998 FDA SANOFI AVENTIS US

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC J04AB05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Antibiotics
FDA CS M0019113 Rifamycins
FDA EPC N0000175501 Rifamycin Antimycobacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000904 Antibiotics, Antitubercular
MeSH PA D000995 Antitubercular Agents
MeSH PA D007917 Leprostatic Agents
CHEBI has role CHEBI:33231 antitubercular
CHEBI has role CHEBI:35816 leprostatic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pulmonary tuberculosis indication 154283005 DOID:2957
Alcoholism contraindication 7200002
Hyperbilirubinemia contraindication 14783006 DOID:2741
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Pseudomembranous enterocolitis contraindication 397683000
Porphyria contraindication 418470004

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.06 acidic
pKa2 7.26 acidic
pKa3 11.03 acidic
pKa4 11.77 acidic
pKa5 12.55 acidic
pKa6 7.87 Basic
pKa7 2.32 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Bacterial DNA-directed RNA polymerase Enzyme INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
4021127 VUID
N0000148581 NUI
D00879 KEGG_DRUG
4021127 VANDF
C0073372 UMLSCUI
CHEBI:45304 CHEBI
RPT PDB_CHEM_ID
CHEMBL1660 ChEMBL_ID
DB01201 DRUGBANK_ID
135403821 PUBCHEM_CID
C018421 MESH_SUPPLEMENTAL_RECORD_UI
4765 INN_ID
XJM390A33U UNII
35617 RXNORM
7483 MMSL
d04327 MMSL
007675 NDDF
108686006 SNOMEDCT_US
410831004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Priftin HUMAN PRESCRIPTION DRUG LABEL 1 0088-2102 TABLET, FILM COATED 150 mg ORAL NDA 30 sections
Priftin HUMAN PRESCRIPTION DRUG LABEL 1 50090-5063 TABLET, FILM COATED 150 mg ORAL NDA 29 sections