Rifapentine (T3D3018)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-07-21 20:28:37 UTC
Update Date2014-12-24 20:25:55 UTC
Accession NumberT3D3018
Identification
Common NameRifapentine
ClassSmall Molecule
DescriptionRifapentine is only found in individuals that have used or taken this drug. It is an antibiotic drug used in the treatment of tuberculosis. Rifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages. Rifapentine inhibits DNA-dependent RNA polymerase in susceptible strains of M. tuberculosis. Rifapentine acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death.
Compound Type
  • Amide
  • Amine
  • Antibiotic, Antitubercular
  • Antimycobacterial
  • Drug
  • Ester
  • Ether
  • Hydrazine
  • Leprostatic Agent
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin
Cyclopentyl rifampin
Cyclopentylrifampicin
Priftin
Chemical FormulaC47H64N4O12
Average Molecular Mass877.031 g/mol
Monoisotopic Mass876.452 g/mol
CAS Registry Number61379-65-5
IUPAC Name(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,21Z)-26-[(1E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl]-2,15,17,23,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6-oxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-13-yl acetate
Traditional Name(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,21Z)-26-[(1E)-[(4-cyclopentylpiperazin-1-yl)imino]methyl]-2,15,17,23,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6-oxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-13-yl acetate
SMILES[H]\C(=N/N1CCN(CC1)C1CCCC1)C1=C(O)C2=C3C(O)=C(C)C4=C2C(=O)[C@](C)(O4)O\C([H])=C([H])/[C@]([H])(OC)[C@@]([H])(C)[C@@]([H])(OC(C)=O)[C@]([H])(C)[C@]([H])(O)[C@]([H])(C)[C@@]([H])(O)[C@@]([H])(C)C([H])=C([H])\C([H])=C(C)/C(O)=NC1=C3O
InChI IdentifierInChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17-,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
InChI KeyInChIKey=WDZCUPBHRAEYDL-IWVAIHGYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthofurans
Sub ClassNot Available
Direct ParentNaphthofurans
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility2.13e-02 g/L
LogP4
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.74ALOGPS
logP3.82ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
pKa (Strongest Basic)15.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area223.64 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity242.75 m³·mol⁻¹ChemAxon
Polarizability93.79 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0300000190-d118c1ac8e3c60e6452b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-2100002290-b441d6ad4afc88a626242016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9700006020-ee8161658ea49259d1682016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0100001290-6aa51e29ae4edc2dea4f2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-2500003190-ac076b0cb13b991b003a2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9200008320-465071920392bca6a7792016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0000000390-f812402cd842a853749c2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0690-0000000190-f6ddb4327cad4885918e2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cfr-7600001490-17f0e57624f1de4d2dee2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1000000290-3b4cef67ccc26d401a392021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000010-4e966171b9c3614260a02021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9500006520-7a1bb51257442c63c7842021-10-11View Spectrum
Toxicity Profile
Route of ExposureRapidly and well absorbed from the gastrointestinal tract.
Mechanism of ToxicityRifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages. Rifapentine inhibits DNA-dependent RNA polymerase in susceptible strains of M. tuberculosis. Rifapentine acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death.
MetabolismHepatic Route of Elimination: Following a single 600 mg oral dose of radiolabeled rifapentine to healthy volunteers (n=4), 87% of the total 14C rifapentine was recovered in the urine (17%) and feces (70%).
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of pulmonary tuberculosis.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01201
HMDB IDHMDB15332
PubChem Compound ID6323497
ChEMBL IDCHEMBL1660
ChemSpider ID4883449
KEGG IDC08059
UniProt IDNot Available
OMIM ID
ChEBI ID8861
BioCyc IDNot Available
CTD IDNot Available
Stitch IDRifapentine
PDB IDRPT
ACToR IDNot Available
Wikipedia LinkRifapentine
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Drugs.com [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available