| Identification | Back Directory | [Name]
FidaxoMicin | [CAS]
873857-62-6 | [Synonyms]
OPT-80
CS-741
Dificid
PAR-101
fedamycin
FidaxoMicin
Fidaxomycin
FidaxoMicinr
Not for drug
Lipiarmycin A3
Clostomicin B1
R-Tiacumicin B
Fidaxomicin, >=98%
US-DMF No.: 028803
fidaxomicin,Dificid
Fidaxomicin (OPT-80)
FidaxoMicin USP/EP/BP
Fidaxomicin Crystalline
FidaxoMicin(LipiarMycin)
Fidaxomicin
R-Tiacumicin B
OPT-80;PAR-101;CLOSTOMICIN B1;TIACUMICIN B
ClostoMicin B1, LipiarMycin A3, TiacuMicin B, OPT 80
FidaxomicinQ: What is
Fidaxomicin Q: What is the CAS Number of
Fidaxomicin Q: What is the storage condition of
Fidaxomicin Q: What are the applications of
Fidaxomicin
Fidaxomicin D7Q: What is
Fidaxomicin D7 Q: What is the CAS Number of
Fidaxomicin D7 Q: What is the storage condition of
Fidaxomicin D7 Q: What are the applications of
Fidaxomicin D7
3-(((6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-b-D-mannopyranosyl)oxy)-methyl)-12(R)-[(6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-b-D-lyxo-hexopyranosyl)oxy]-11(S)-eth
3-(((6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-b-D-mannopyranosyl)oxy)-methyl)-12(R)-[(6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-b-D-lyxo-hexopyranosyl)oxy]-11(S)-ethyl-8(S)-hydro
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)-hydroxy
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
3-(((6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-b-D-mannopyranosyl)oxy)-methyl)-12(R)-[(6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-b-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
Oxacyclooctadeca-3,5,9,13,15-pentaen-2-one, 3-[[[6-deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-β-D-mannopyranosyl]oxy]methyl]-12-[[6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-β-D-lyxo-hexopyranosyl]oxy]-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-, (3E,5E,8S,...
Oxacyclooctadeca-3,5,9,13,15-pentaen-2-one, 3-[[[6-deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-β-D-mannopyranosyl]oxy]methyl]-12-[[6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-β-D-lyxo-hexopyranosyl]oxy]-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-, (3E,5E,8S,9E,11S,12R,13E,15E,18S)-
(2R,3S,4S,5S,6R)-6-(((3E,5E,8S,9E,11S,12R,13E,15E,18S)-12-(((2R,3S,4R,5S)-3,4-Dihydroxy-5-(isobutyryloxy)-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-11-ethyl-8-hydroxy-18-((R)-1-hydroxyethyl)-9,13,15-trimethyl-2-oxooxacyclooctadeca-3,5,9,13,15-pentaen-3-yl)methoxy)-4-hydroxy-5-methoxy-2-methyltetrahydro-2H-pyran-3-yl 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate | [Molecular Formula]
52H74Cl2O18 | [MDL Number]
MFCD27976367 | [MOL File]
873857-62-6.mol | [Molecular Weight]
1058.04 |
| Chemical Properties | Back Directory | [Melting point ]
161 °C | [Boiling point ]
1046.4±65.0 °C(Predicted) | [density ]
1.33 | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly) | [form ]
powder | [pka]
5.09±0.35(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Description]
Fidaxomicin (OPT-80) was approved by the U.S. FDA in May 2011 for
the treatment of Clostridium difficile-associated diarrhea (CDAD), joining
metronidazole and vancomycin as drugs recommended for treatment of
C. difficile infections (CDI). Fidaxomicin, also known as
lipiarmycin and tiacumicin, is an 18-membered macrolide natural
product that was first reported in mid-1970s and is produced by
fermentation. Fidaxomicin and its primary metabolite OP-1118,
which results from hydrolysis of the isobutyryl ester, are narrowspectrum
antibacterial agents with activity against gram-positive aerobic
and anaerobic organisms, but not against gram-negative organisms.
Fidaxomicin and OP-1118 exert their antibacterial activity by inhibiting
bacterial RNA polymerase, thereby inhibiting bacterial protein
synthesis.
The MIC90 (minimum inhibitory concentration to kill 90% of
bacteria) for fidaxomicin against C.difficile is 0.125–0.25 μg/mL; OP-
1118 is 4- to 16-fold less potent than the parent compound.
Fidaxomicin has been reported to spare native intestinal flora such as
Bacteroides spp. and as such, may prevent selection of drug-resistant
bacteria. Fidaxomicin is bactericidal to C. difficile and has a low
propensity for resistance development with no cross-resistance to
existing antibiotics. Fidaxomicin shows minimal systemic absorption following oral administration in preclinical studies and humans. | [Originator]
Optimer Pharmaceuticals (United States) | [Uses]
Fidaxomicin is a recently marketed antibiotic with a confusing history dating back to its original isolation in 1975. Fidaxomicin is the major analogue of a family of macrocyclic lactones, isolated independently by three different groups from cultures belonging to three different genera (Actinoplanes, Dactylosporangium and Micromonospora) known as lipiarmycin A3, tiacumicin B and clostomicin B1, respectively. Fidaxomicin is a narrow spectrum antibiotic with excellent activity against Gram positive bacteria, notably Clostridium difficile. Fidaxomicin acts in the gastrointestinal tract without undue disruption to gut microbial flora. | [Uses]
Fidaxomycin is a natural macrocyclic antibiotic that inhibits RNA polymerase with selectivity for Gram-positive bacteria over Gram-negative bacteria (IC50s = 0.4 and 6 μM, respectively). It has potent antibacterial activity against most Gram-positive bacteria and effectively targets the Gram-positive C. difficile (MIC = 12 ng/ml). Orally administered fidaxomycin exhibits minimal systemic bioavailability resulting in maximal gastrointestinal tract distribution. Fidaxomycin is effective in clearing C. difficile infections while sparing Gram-negative bacteria in the gut.[Cayman Chemical] | [Definition]
ChEBI: An 18-membered macrolide that is a fermentation product obtained from the Actinomycete Dactylosporangium aurantiacum. A narrow spectrum antibiotic used for treatment of Clostridium difficile-related infections. | [Brand name]
Dificid | [Pharmaceutical Applications]
Formerly known as difimicin. An 18-membered macrocyclic
compound related to the tiacumicin group of antibiotics
rather than conventional macrolides. It is active against
staphylococci (MIC 0.5–2 mg/L) and most anaerobic Grampositive
bacilli and cocci, but Gram-negative bacilli, including
Gram-negative anaerobes, are resistant. It is very poorly
absorbed when given orally and most interest surrounds its
activity against C. difficile (MIC 0.12–0.25 mg/L). Such data
as are presently available from clinical trials suggest that it is
as safe and effective in the treatment of C. difficile-associated
diarrhea as vancomycin. | [Biochem/physiol Actions]
Fidaxomicin is a first-in-class macrocyclic antibacterial agent for gram positive bacteria treatment, notably Clostridium difficile infections. Fidaxomicin produces its antibacterial effects by inhibiting bacterial RNA polymerase at transcription initiation. Furthermore, Fidaxomicin is an inhibitor of bacterial transcription. Fidaxomicin acts at an earlier step in the transcription initiation pathway. Specifically, Fidaxomicin binds to the DNA template-RNA polymerase complex and prevents the initial separation of DNA strands, which precedes messenger RNA synthesis by inhibiting the s subunit. Fidaxomicin′s unique target site may explain its limited spectrum of antimicrobial activity because s subunits differ among bacterial species. | [Clinical Use]
Macrolide antibacterial agentTreatment of Clostridium Difficile infection | [Drug interactions]
Potentially hazardous interactions with other drugs
Anti-arryhthmics: avoid concomitant use with
amiodarone and dronedarone.
Antibaterials: avoid concomitant use with
clarithromycin and erythromycin.
Antifungals: avoid concomitant use with
ketoconazole.
Calcium channel blockers: avoid concomitant use
with verapamil.
Ciclosporin: increased fidaxomicin levels, avoid
concomitant use. | [Metabolism]
Mainly metabolised by hydrolysis in the gut at the
isobutyryl ester to form its main and microbiologically
active metabolite, OP-1118. Over 92% of a dose is
excreted in the faeces as either fidaxomicin or OP-1118,
although very small amounts of OP-1118 have been
recovered in the urine | [storage]
Store at -20°C |
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