Chemical Component Summary

NameRIFAPENTINE
Synonyms(2R,16S,17R,18R,19R,20S,21S,22S,23S)-8-{[(4-CYCLOPENTYLPIPERAZIN-1-YL)IMINO]METHYL}-5,6,9,17,19-PENTAHYDROXY-23-METHOXY-2,4,12,16,18,20,22-HEPTAMETHYL-1,11-DIOXO-1,2-DIHYDRO-2,7-(EPOXYPENTADECA[1,11,13]TRIENOIMINO)NAPHTHO[2,1-B]FURAN-21-YL ACETATE; 3-(((4-CYCLOPENTYL-1-PIPERAZINYL)IMINO)METHYL)RIFAMYCIN
Identifiersn/a
FormulaC47 H64 N4 O12
Molecular Weight877.031
TypeNON-POLYMER
Isomeric SMILESCc1c(c2c3c4c1O[C@@](C4=O)(O\C=C\[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](\C=C\C=C(/C(=O)Nc(c2O)c(c3O)\C=N\N5CCN(CC5)C6CCCC6)\C)C)O)C)O)C)OC(=O)C)C)OC)C)O
InChIInChI=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
InChIKeyWDZCUPBHRAEYDL-GZAUEHORSA-N

Chemical Details

Formal Charge0
Atom Count127
Chiral Atom Count9
Bond Count132
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB01201 
NameRifapentine
Groups
  • approved
  • investigational
DescriptionRifapentine is an antibiotic drug used in the treatment of tuberculosis. It inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme.
Synonyms
  • 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin
  • Rifapentin
  • Rifapentine hydrochloride
  • Rifapentine
  • Cyclopentylrifampicin
Brand NamesPriftin
IndicationFor the treatment of pulmonary tuberculosis.
Categories
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics, Antitubercular
  • Antiinfectives for Systemic Use
  • Antimycobacterials
ATC-CodeJ04AB05
CAS number61379-65-5

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA-directed RNA polymerase subunit beta'MLDVNFFDELRIGLATAEDIRQWSYGEVKKPETINYRTLKPEKDGLFCEK...unknowninhibitor
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninducer
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknowninducer
Cytochrome P450 3A SubfamilyMALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknowninducer
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknowninducer
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 135403821
ChEMBL CHEMBL1660
ChEBI CHEBI:45304