Compound ID | 2007

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Fidaxomicin

Synonym(s): Tiacumicin B  |  lipiarmycin  |  OPT-80  |  PAR-101  |  dificlir  |  dificid

Class: Macrolide (18-membered macrolide, tiacumicin)

Spectrum of activity: Gram-positive
Details of activity: Binds to the DNA template-RNA polymerase complex and inhibits the initiation of RNA chain synthesis and transcription. It is active against Clostridioides difficile.
Description: Macrocylic natural product produced by Dactylosporangium. Oral application without relevant absorption for C. difficile associated diarrhea
Year first mentioned: 1980
Development status: Approved
Chemical structure(s):
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Molecular weight: 1058.04
Iso. SMILES: CC[C@H]1/C=C(/[C@H](C/C=C/C=C(/C(=O)O[C@@H](C/C=C(/C=C(/[C@@H]1O[C@H]2[C@H]([C@H]([C@@H](C(O2)(C)C)OC(=O)C(C)C)O)O)\C)\C)[C@@H](C)O)\CO[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)\C
InChI Key: ZVGNESXIJDCBKN-UUEYKCAUSA-N
Can. SMILES: CC[C@H]1/C=C(\C)/[C@H](C/C=C/C=C(\CO[C@H]2[C@H]([C@H]([C@@H]([C@@H](C)O2)OC(=O)C3=C(C(=C(C(=C3CC)Cl)O)Cl)O)O)OC)/C(=O)O[C@@H](C/C=C(\C)/C=C(\C)/[C@@H]1O[C@H]4[C@H]([C@H]([C@@H](C(C)(C)O4)OC(=O)C(C)C)O)O)[C@@H](C)O)O
InChI: InChI=1S/C52H74Cl2O18/c1-13-30-22-26(6)33(56)18-16-15-17-31(23-66-51-45(65-12)42(61)44(29(9)67-51)69-49(64)35-32(14-2)36(53)39(58)37(54)38(35)57)48(63)68-34(28(8)55)20-19-25(5)21-27(7)43(30)70-50-41(60)40(59)46(52(10,11)72-50)71-47(62)24(3)4/h15-17,19,21-22,24,28-30,33-34,40-46,50-51,55-61H,13-14,18,20,23H2,1-12H3/b16-15+,25-19+,26-22+,27-21+,31-17+/t28-,29-,30+,33+,34+,40-,41+,42+,43+,44-,45+,46+,50-,51-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/10034073
Guide to Pharmacology: fidaxomicin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/35964806/
  • https://pubmed.ncbi.nlm.nih.gov/36057672/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC284295/
  • https://www.jstage.jst.go.jp/article/antibiotics1968/41/3/41_3_308/_pdf/-char/en

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