Fidaxomicinmacrocyclic antibiotic CAS# 873857-62-6 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 873857-62-6 | SDF | Download SDF |
| PubChem ID | 10034073 | Appearance | Powder |
| Formula | C52H74Cl2O18 | M.Wt | 1058.04 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 33 mg/mL (31.19 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical 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-methylpropanoyloxy)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 | ||
| 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 | ||
| Standard InChIKey | ZVGNESXIJDCBKN-UUEYKCAUSA-N | ||
| Standard 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Fidaxomicin(OPT-80; PAR-101) is a new class of narrow spectrum macrocyclic antibiotic drug; selective eradication of pathogenic Clostridium difficile with minimal disruption to the multiple species of bacteria that make up the normal, healthy intestinal flora. References: | |||||
Fidaxomicin Dilution Calculator
Fidaxomicin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 0.9451 mL | 4.7257 mL | 9.4514 mL | 18.9029 mL | 23.6286 mL |
| 5 mM | 0.189 mL | 0.9451 mL | 1.8903 mL | 3.7806 mL | 4.7257 mL |
| 10 mM | 0.0945 mL | 0.4726 mL | 0.9451 mL | 1.8903 mL | 2.3629 mL |
| 50 mM | 0.0189 mL | 0.0945 mL | 0.189 mL | 0.3781 mL | 0.4726 mL |
| 100 mM | 0.0095 mL | 0.0473 mL | 0.0945 mL | 0.189 mL | 0.2363 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Fidaxomicin is a macrocyclic antibiotic that inhibits RNA polymerase sigma subunit [1].
Antibiotics are a type of antimicrobial used in the treatment of bacterial infection. They can inhibit the growth of bacteria. Bacterial RNA polymerase mediates RNA synthesis.
Fidaxomicin is a narrow spectrum antibiotic that inhibits RNA polymerase sigma subunit. Fidaxomicin was a macrocyclic-lactone antibiotic produced by Actinomycete species. Fidaxomicin inhibited RNA polymerase in Clostridium difficile [1].
In patients infected with Clostridium difficile, fidaxomicin exhibited a higher clinical cure rate and a lower recurrence rate. In rats, fidaxomicin was safe by the intravenous route and exhibited LD50 value of 200 mg/kg. Fidaxomicin for the treament of Clostridium difficile infection (CDI) had entered Phase III trials [2]. In patients with CDI, fidaxomicin exhibited a lower reappearance of toxin in fecal filtrates and inhibited recurrence of CDI. Also, fidaxomicin preserved the intestinal microbiome during the treatment of CDI [3].
References:
[1]. Srivastava A, Talaue M, Liu S, et al. New target for inhibition of bacterial RNA polymerase: 'switch region'. Curr Opin Microbiol, 2011, 14(5): 532-543.
[2]. Poxton IR. Fidaxomicin: a new macrocyclic, RNA polymerase-inhibiting antibiotic for the treatment of Clostridium difficile infections. Future Microbiol, 2010, 5(4): 539-548.
[3]. Louie TJ, Cannon K, Byrne B, et al. Fidaxomicin preserves the intestinal microbiome during and after treatment of Clostridium difficile infection (CDI) and reduces both toxin reexpression and recurrence of CDI. Clin Infect Dis, 2012, 55 Suppl 2: S132-S142.
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Final Demonstration of the Co-Identity of Lipiarmycin A3 and Tiacumicin B (Fidaxomicin) through Single Crystal X-ray Analysis.[Pubmed:28208717]
Antibiotics (Basel). 2017 Feb 8;6(1). pii: antibiotics6010007.
Lipiarmycin A3 and tiacumicin B possess the same chemical structure and have been considered identical till recently, when some authors have suggested the possibility of a minor difference between the chemical structures of the two antibiotics. In this work we performed a comparative X-ray analysis of lipiarmycin A3 and tiacumicin B. Although the commercial samples of the aforementioned compounds crystallize into two different crystal systems-evidently due to the different crystallization conditions-their chemical structures are identical. These results confirmed the previous assigned chemical structure of lipiarmycin A3 and its absolute configuration as well as its co-identity with the chemical structure of tiacumicin B, providing the definitive proof that these pharmaceutical compounds are identical in all respects.
IVIG - A cure to severe refractory NAP-1 Clostridium difficile colitis? A case of successful treatment of severe infection, which failed standard therapy including fecal microbiota transplants and fidaxomicin.[Pubmed:28331803]
IDCases. 2017 Mar 6;8:27-28.
The mainstay treatment of Clostridium difficile infections (CDI) is antimicrobials with growing support for fecal microbiota transplants. We report the first case of an elderly man with severe refractory NAP-1 pseudomembranous CDI who failed all medical therapy and two fecal transplants with response only seen after administration of intravenous immunoglobulin.
Cost-effectiveness analysis on the use of fidaxomicin and vancomycin to treat Clostridium difficile infection in France.[Pubmed:28299963]
J Med Econ. 2017 Jul;20(7):678-686.
BACKGROUND: Fidaxomicin is a macrocyclic antibiotic with proven efficacy against Clostridium difficile infection (CDI) in adults. It was licensed in France in 2012, but, due to higher acquisition costs compared with existing treatments, healthcare providers require information on its cost/benefit profile. OBJECTIVE: To compare healthcare costs and health outcomes of Fidaxomicin and vancomycin, as reference treatment for CDI. METHODS: A Markov model was used to simulate the treatment pathway, over 1 year, of adult patients with CDI receiving Fidaxomicin or vancomycin. Several patient sub-groups (severe CDI; recurrent CDI; concomitant antibiotics; cancer; renal failure; elderly) were evaluated. Cost-effectiveness was analyzed based on cure and recurrence rates derived from published randomized clinical trials comparing Fidaxomicin and vancomycin, and costs calculated from the payer perspective using French hospitalization data and drug cost databases. Model outputs included costs in euros (reference year 2014) and health outcomes (recurrence; sustained cure rates). Alternative scenario and sensitivity analyses were performed using data from other clinical trials in CDI, including one conducted in real-life clinical practice in France. RESULTS: Drug acquisition costs were euro1,692 higher in Fidaxomicin-treated patients, but this was offset by the lower hospitalization costs with Fidaxomicin, which were reduced by euro1,722. The reduction in the cost of hospitalization was driven by the significantly lower number of recurrences in Fidaxomicin-treated patients, offsetting the acquisition cost of Fidaxomicin in all sub-groups except recurrent CDI and concomitant antibiotics. CONCLUSION: This study demonstrated that, despite higher acquisition costs, the lower recurrence rate with Fidaxomicin resulted in cost savings or low incremental costs compared with vancomycin.
Fidaxomicin for treatment of Clostridium difficile infection in clinical practice: a prospective cohort study in a French University Hospital.[Pubmed:28120176]
Infection. 2017 Aug;45(4):425-431.
PURPOSE: Two randomized controlled trials (RCTs) showed the non-inferiority of Fidaxomicin compared with vancomycin for Clostridium difficile infection (CDI) treatment and its superiority regarding recurrence rate. The aim of this study was to evaluate Fidaxomicin's efficacy in clinical practice. METHODS: This single-center prospective cohort study included hospitalized patients treated with Fidaxomicin for CDI. Demographic, clinical and biological data were collected. Primary outcome was efficacy of Fidaxomicin (clinical cure, recurrence and global cure) at 10 weeks. Secondary outcome was efficacy among different subgroups. RESULTS: Ninety-nine patients were included: 42 severe CDI, 16 complicated CDI and 41 recurrent CDI. Rates of clinical cure, recurrence and global cure were 87, 15 and 59%, respectively. Subgroup analysis showed a higher recurrence rate for patients with recurrent CDI compared with first episode (8 vs. 26%; p = 0.04). Binary toxin was associated with severe/complicated CDI (80 vs. 50%; p < 0.01) and recurrence (32 vs. 7%; p < 0.01). Fidaxomicin was used as a first line for 83% of the patients with recurrence and for only 52% of first episodes even though 86% had recurrence's risk factors. CONCLUSION: Compared with RCTs, Fidaxomicin in real world is used for patients with more severe and recurrent CDI, but clinical cure and recurrence rates were similar. Comparative studies are needed in these specific subgroups. Our data also illustrate clinicians' difficulty to define a "patient at risk for recurrence" among the first episodes. Finally, we showed that binary toxin could be important in the screening for severity and recurrence risks.
