2D 3D
	ID	DDInter734
	Drug Type	small molecule
	Molecular Formula	C52H74Cl2O18
	Molecular Weight	1058.050
	CAS Number	873857-62-6
	Description	Fidaxomicin is a novel macrolide antibiotic used in the treatment of diarrhea caused by _Clostridioides_ (formerly _Clostridium_) _difficile_ in adult and pediatric patients over the age of 6 months.[L11575] Fidaxomicin is a naturally-occurring 18-member macrocycle derived from fermentation.[A190501] Because fidaxomicin contains an 18-membered lactone ring in its structure, it is referred to as a macrocyclic lactone antibiotic drug.[A190492] The antibacterial activity of fidaxomicin is distinct from macrolides and rifamycins, as the bactericidal activity is time-dependent, and not concentration-dependent.[A190492] Fidaxomicin was the first macrocyclic lactone antibiotic with activity against _C. difficile_,[A190486] and it displays a narrow spectrum of activity against gram-positive anaerobes.[A7445] It mediates its potent bactericidal action on the bacteria by inhibiting the bacterial RNA synthase, thereby disrupting bacterial transcription.[A190486] The minimum inhibitory concentration (MIC90) for fidaxomicin is four times less than that of [vancomycin], which was the primary drug of choice for _C. difficile_ infection before the approval of fidaxomicin.[A190492] Unlike vancomycin, however, fidaxomicin has a negligible effect on normal colonic microflora.[A190516] The FDA initially approved fidaxomicin in May 2011 for the treatment of _C. difficile_-associated diarrhea in adult patients over the age of 18.[A190492] Later that year in December, the drug was also approved by the European Medicine Agency.[A190492] In June 2012, fidaxomicin was also granted approval by Health Canada.[A190486] The approved indication of fidaxomicin was expanded by the FDA in January 2020 to include pediatric patients over the age of 6 months in the treatment population.[L11575]
	ATC Classification	A07AA12
IUPAC Name	(2R,3S,4S,5S,6R)-6-{[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-12-{[(2R,3S,4R,5S)-3,4-dihydroxy-6,6-dimethyl-5-[(2-methylpropanoyl)oxy]oxan-2-yl]oxy}-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy}-4-hydroxy-5-methoxy-2-methyloxan-3-yl 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate
InChI	ZVGNESXIJDCBKN-UUEYKCAUSA-N
Canonical SMILES	[H][C@@]1(O[C@@H]2[C@@H](CC)\C=C(C)\[C@@H](O)C\C=C\C=C(CO[C@@H]3O[C@H](C)[C@@H](OC(=O)C4=C(CC)C(Cl)=C(O)C(Cl)=C4O)[C@H](O)[C@@H]3OC)\C(=O)O[C@@H](C\C=C(/C)\C=C2/C)[C@@H](C)O)OC(C)(C)[C@@H](OC(=O)C(C)C)[C@H](O)[C@@H]1O
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