CID 151383

Base Information

• Chemical Name: CID 151383
• CAS No.: 873857-62-6
• Molecular Formula: C52H74Cl2O18
• Molecular Weight: 1058.04
• Hs Code.: 2941900000
• European Community (EC) Number: 692-555-6
• Wikipedia: Fidaxomicin
• Wikidata: Q105384285,Q110204142
• NCI Thesaurus Code: C66979
• RXCUI: 1111103
• Mol file: 873857-62-6.mol

Synonyms:Dificid;fidaxomicin;lipiarmycin;lipiarmycin A3;lipiarmycin A4;lipiarmycin B;lipiarmycin B3;lipiarmycin B4;PAR 101;PAR-101;PAR101;tiacumicin B;tiacumicin C

Chemical Property of CID 151383

Chemical Property:

• Melting Point: 161 °C
• Boiling Point: 1046.4±65.0 °C(Predicted)
• PKA: 5.09±0.35(Predicted)
• PSA: 266.66000
• Density: 1.33
• LogP: 6.23440
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 15
• Exact Mass: 1056.4252209
• Heavy Atom Count: 72
• Complexity: 1970

Purity/Quality:

99%min ^*data from raw suppliers

Fidaxomicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CCC1C=C(C(CC=CC=C(C(=O)OC(CC=C(C=C(C1OC2C(C(C(C(O2)(C)C)OC(=O)C(C)C)O)O)C)C)C(C)O)COC3C(C(C(C(O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)C
• Recent EU Clinical Trials: A randomised, controlled, open-label phase III clinical trial in patients with recurrent Clostridioides difficile (CD) infection, to evaluate the efficacy and safety of capsules of lyophilised faecal microbiota vs fidaxomicin
• 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.
• Uses: Fidaxomicin is a nonabsorbed macrocyclic antibiotic, and is the first antimicrobial to be approved by the FDA for the treatment of Clostridium difficile infection (CDI) in 20 years. Fidaxomicin works by inhibiting sporulation by CDI, sustaining clinical response and reducing recurrences of this pathogen. 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. 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]
• 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.