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Fidaxomicin

Fidaxomicin
Clinical data
Trade namesDificid, Dificlir
Other namesClostomicin B1, lipiarmicin, lipiarmycin, lipiarmycin A3, OPT-80, PAR 01, PAR-101, tiacumicin B
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityMinimal systemic absorption[2]
Elimination half-life11.7 ± 4.80 hours[2]
ExcretionUrine (<1%), faeces (92%)[2]
Identifiers
  • 3-(((6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-β-D-mannopyranosyl)oxy)-methyl)-12(R)-[(6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-β-D-lyxo-hexopyranosyl)oxy]-11(S)-ethyl-8(S)-hydroxy-18(S)-(1(R)-hydroxyethyl)-9,13,15-trimethyloxacyclooctadeca-3,5,9,13,15-pentaene-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.220.590 Edit this at Wikidata
Chemical and physical data
FormulaC52H74Cl2O18
Molar mass1058.05 g·mol−1
3D model (JSmol)
  • 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=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 ☒N
  • Key:ZVGNESXIJDCBKN-UUEYKCAUSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Fidaxomicin, sold under the brand name Dificid (by Merck) among others, is the first member of a class of narrow spectrum macrocyclic antibiotic drugs called tiacumicins.[3] It is a fermentation product obtained from the actinomycete Dactylosporangium aurantiacum subspecies hamdenesis.[4][5] Fidaxomicin is minimally absorbed into the bloodstream when taken orally, is bactericidal, and selectively eradicates pathogenic Clostridioides difficile with relatively little disruption to the multiple species of bacteria that make up the normal, healthy intestinal microbiota. The maintenance of normal physiological conditions in the colon may reduce the probability of recurrence of Clostridioides difficile infection.[6][7]

It is marketed by Merck, which acquired Cubist Pharmaceuticals in 2015, and had in turn bought the originating company, Optimer Pharmaceuticals. It is used for the treatment of Clostridioides difficile infection, which is also known as Clostridioides difficile-associated diarrhea or Clostridioides difficile-associated illness (CDI), and can develop into Clostridioides difficile colitis and pseudomembranous colitis.

It is approved as a generic medication.[8]

  1. ^ "Dificlir EPAR". European Medicines Agency (EMA). September 17, 2018. Retrieved January 18, 2021.
  2. ^ a b c "Dificid" (PDF). TGA eBusiness Services. Specialised Therapeutics Australia Pty Ltd. April 23, 2013. Retrieved March 31, 2014.
  3. ^ Revill P, Serradell N, Bolos J (2006). "Tiacumicin B". Drugs of the Future. 31 (6): 494. doi:10.1358/dof.2006.031.06.1000709.
  4. ^ "Dificid- fidaxomicin tablet, film coated Dificid- fidaxomicin granule, for suspension". DailyMed. February 18, 2020. Retrieved March 26, 2020.
  5. ^ "Fidaxomicin: Difimicin; Lipiarmycin; OPT 80; OPT-80; PAR 101; PAR-101". Drugs in R&D. 10 (1): 37–45. 2012. doi:10.2165/11537730-000000000-00000. PMC 3585687. PMID 20509714.
  6. ^ Louie TJ, Emery J, Krulicki W, Byrne B, Mah M (January 2009). "OPT-80 eliminates Clostridium difficile and is sparing of bacteroides species during treatment of C. difficile infection". Antimicrobial Agents and Chemotherapy. 53 (1): 261–263. doi:10.1128/AAC.01443-07. PMC 2612159. PMID 18955523.
  7. ^ Johnson S (June 2009). "Recurrent Clostridium difficile infection: a review of risk factors, treatments, and outcomes". The Journal of Infection. 58 (6): 403–410. doi:10.1016/j.jinf.2009.03.010. PMID 19394704.
  8. ^ "First-Time Generic Drug Approvals 2024". U.S. Food and Drug Administration (FDA). March 8, 2024. Retrieved March 9, 2024.
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