Compound ID | 1858

Update compound information

Rifapentine

Synonym(s): DL 473

Class: Rifamycin

Spectrum of activity: Gram-positive
Details of activity: Inhibits bacterial DNA-dependent RNA polymerase, thus inhibiting bacterial RNA synthesis
Combined with other compounds: Yes
Propensity to select resistant mutants: Yes
Description: Semisynthetic, derived from rifamycin. Used mainly for the treatment of tuberculosis in combination
Institute where first reported: Sanofi Aventis US
Year first mentioned: 1965
Highest development stage: Approved by FDA in 1998
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 877.03
Iso. SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N5CCN(CC5)C6CCCC6)/C
InChI Key: WDZCUPBHRAEYDL-GZAUEHORSA-N
Can. SMILES: C[C@H]1/C=C/C=C(/C)\C(=O)NC2=C(C3=C(C(=C4C(=C3C(=C2/C=N/N5CCN(CC5)C6CCCC6)O)C(=O)[C@@](C)(O/C=C/[C@@H]([C@@H](C)[C@H]([C@H](C)[C@@H]([C@H](C)[C@H]1O)O)OC(=O)C)OC)O4)C)O)O
InChI: InChI=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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135403821
Guide to Pharmacology: rifapentine
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/35294822/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8597776/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9186306/
  • https://pubmed.ncbi.nlm.nih.gov/9806107/

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