Fidaxomicin

Fidaxomicin
Clinical data
Trade names	Dificid, Dificlir
Other names	Clostomicin B1, lipiarmicin, lipiarmycin, lipiarmycin A3, OPT-80, PAR 01, PAR-101, tiacumicin B
AHFS/Drugs.com	Monograph
License data	US DailyMed: Fidaxomicin;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
ATC code	A07AA12 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	Minimal systemic absorption
Elimination half-life	11.7 ± 4.80 hours
Excretion	Urine (<1%), faeces (92%)
Identifiers
	IUPAC name 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	873857-62-6 ;
PubChem CID	10034073;
DrugBank	DB08874 ;
ChemSpider	8209640 ;
UNII	Z5N076G8YQ;
KEGG	D09394 ;
ChEBI	CHEBI:68590 ;
ChEMBL	ChEMBL1255800 ;
ECHA InfoCard	100.220.590
Chemical and physical data
Formula	C52H74Cl2O18
Molar mass	1058.05 g·mol−1
3D model (JSmol)	Interactive image;
	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 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 ; Key:ZVGNESXIJDCBKN-UUEYKCAUSA-N ;
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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]

^ "Dificlir EPAR". European Medicines Agency (EMA). September 17, 2018. Retrieved January 18, 2021.
^ ^a ^b ^c "Dificid" (PDF). TGA eBusiness Services. Specialised Therapeutics Australia Pty Ltd. April 23, 2013. Retrieved March 31, 2014.
^ Revill P, Serradell N, Bolos J (2006). "Tiacumicin B". Drugs of the Future. 31 (6): 494. doi:10.1358/dof.2006.031.06.1000709.
^ "Dificid- fidaxomicin tablet, film coated Dificid- fidaxomicin granule, for suspension". DailyMed. February 18, 2020. Retrieved March 26, 2020.
^ "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.
^ 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.
^ 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.
^ "First-Time Generic Drug Approvals 2024". U.S. Food and Drug Administration (FDA). March 8, 2024. Retrieved March 9, 2024.

[1] "Dificlir EPAR". European Medicines Agency (EMA). September 17, 2018. Retrieved January 18, 2021.

[TGA-2] "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.

[PrescribingInfo-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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