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Fidaxomicin

CAS No.:
873857-62-6
Catalog Number:
AG00363N
Molecular Formula:
C52H74Cl2O18
Molecular Weight:
1058.0392
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
≥95%
1 week
United States
$123
- +
50mg
99%
1 week
United States
$182
- +
100mg
99%
1 week
United States
$265
- +
Product Description
Catalog Number:
AG00363N
Chemical Name:
Fidaxomicin
CAS Number:
873857-62-6
Molecular Formula:
C52H74Cl2O18
Molecular Weight:
1058.0392
MDL Number:
MFCD27976367
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-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
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
InChI Key:
ZVGNESXIJDCBKN-UUEYKCAUSA-N
SMILES:
CO[C@@H]1[C@H](OC/C/2=C\C=C\C[C@H](O)/C(=C/[C@H](CC)[C@H](/C(=C/C(=C/C[C@H](OC2=O)[C@H](O)C)/C)/C)O[C@@H]2OC(C)(C)[C@H]([C@@H]([C@@H]2O)O)OC(=O)C(C)C)/C)O[C@@H]([C@H]([C@@H]1O)OC(=O)c1c(O)c(Cl)c(c(c1CC)Cl)O)C
UNII:
Z5N076G8YQ
Properties
Complexity:
1970  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
14  
Defined Bond Stereocenter Count:
5  
Exact Mass:
1056.425g/mol
Formal Charge:
0
Heavy Atom Count:
72  
Hydrogen Bond Acceptor Count:
18  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0
Molecular Weight:
1058.046g/mol
Monoisotopic Mass:
1056.425g/mol
Rotatable Bond Count:
15  
Topological Polar Surface Area:
267A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.4  
Literature
Title Journal
Decreased cure and increased recurrence rates for Clostridium difficile infection caused by the epidemic C. difficile BI strain. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Relapse versus reinfection: recurrent Clostridium difficile infection following treatment with fidaxomicin or vancomycin. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Safety analysis of fidaxomicin in comparison with oral vancomycin for Clostridium difficile infections. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Reduced acquisition and overgrowth of vancomycin-resistant enterococci and Candida species in patients treated with fidaxomicin versus vancomycin for Clostridium difficile infection. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Fidaxomicin is an inhibitor of the initiation of bacterial RNA synthesis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Fidaxomicin preserves the intestinal microbiome during and after treatment of Clostridium difficile infection (CDI) and reduces both toxin reexpression and recurrence of CDI. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Renal failure and leukocytosis are predictors of a complicated course of Clostridium difficile infection if measured on day of diagnosis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Treatment of first recurrence of Clostridium difficile infection: fidaxomicin versus vancomycin. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Fidaxomicin inhibits spore production in Clostridium difficile. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
Fidaxomicin versus vancomycin for Clostridium difficile infection: meta-analysis of pivotal randomized controlled trials. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120801
New drugs 2012, part 2. Nursing 20120701
Fidaxomicin: a novel macrocyclic antibiotic for the treatment of Clostridium difficile infection. American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20120601
Efficacy and safety of fidaxomicin compared with oral vancomycin for the treatment of adults with Clostridium difficile-associated diarrhea: data from the OPT-80-003 and OPT-80-004 studies. Future microbiology 20120601
Fidaxomicin versus vancomycin for infection with Clostridium difficile in Europe, Canada, and the USA: a double-blind, non-inferiority, randomised controlled trial. The Lancet. Infectious diseases 20120401
Progress with a difficult infection. The Lancet. Infectious diseases 20120401
Fidaxomicin: a novel macrocyclic antibiotic approved for treatment of Clostridium difficile infection. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120215
Annual drug update: 2011 in review. The Nurse practitioner 20120212
Clostridium difficile infection in older adults: a review and update on its management. The American journal of geriatric pharmacotherapy 20120201
Fidaxomicin for the treatment of Clostridium difficile infections. The Annals of pharmacotherapy 20120201
Fidaxomicin, a new treatment for Clostridium difficile infections. Drugs of today (Barcelona, Spain : 1998) 20120201
Fidaxomicin: the newest addition to the armamentarium against Clostridium difficile infections. Clinical therapeutics 20120101
Fidaxomicin for Clostridium difficile-associated diarrhoea: epidemiological method for estimation of warranted price. Clinical drug investigation 20120101
Fidaxomicin: in Clostridium difficile infection. Drugs 20111224
Comparative effectiveness of Clostridium difficile treatments: a systematic review. Annals of internal medicine 20111220
Clostridium difficile infection: clinical spectrum and approach to management. Indian journal of gastroenterology : official journal of the Indian Society of Gastroenterology 20111201
Efficacy of fidaxomicin versus vancomycin as therapy for Clostridium difficile infection in individuals taking concomitant antibiotics for other concurrent infections. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20110901
Fidaxomicin: a macrocyclic antibiotic for the treatment of Clostridium difficile infection. Pharmacotherapy 20110901
Killing kinetics of fidaxomicin and its major metabolite, OP-1118, against Clostridium difficile. Journal of medical microbiology 20110801
Characterization of a sugar-O-methyltransferase TiaS5 affords new Tiacumicin analogues with improved antibacterial properties and reveals substrate promiscuity. Chembiochem : a European journal of chemical biology 20110725
Use of alternative or adjuvant pharmacologic treatment strategies in the prevention and treatment of Clostridium difficile infection. International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases 20110701
Fidaxomicin: first-in-class macrocyclic antibiotic. Expert review of anti-infective therapy 20110701
Fewer recurrent infections of C. difficile seen with fidaxomicin. This new class of antibiotic--the macrocycles--has a greater sustained response against re-infection than vancomycin. Managed care (Langhorne, Pa.) 20110701
Fidaxomicin for Clostridium difficile Infection. The New England journal of medicine 20110512
Fidaxomicin for Clostridium difficile infection. The New England journal of medicine 20110512
Fidaxomicin versus vancomycin for Clostridium difficile infection. The New England journal of medicine 20110203
The search for effective treatment of Clostridium difficile infection. The New England journal of medicine 20110203
Characterization of tiacumicin B biosynthetic gene cluster affording diversified tiacumicin analogues and revealing a tailoring dihalogenase. Journal of the American Chemical Society 20110202
'Game changer' antibiotic and others in works for superbug. Nature medicine 20110101
Rivaroxaban, ticagrelor, and fidaxomicin. Journal of the American Pharmacists Association : JAPhA 20110101
Management of Clostridium difficile infection: thinking inside and outside the box. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20101201
A new macrocyclic antibiotic, fidaxomicin (OPT-80), causes less alteration to the bowel microbiota of Clostridium difficile-infected patients than does vancomycin. Microbiology (Reading, England) 20101101
New antibiotics for selective treatment of gastrointestinal infection caused by Clostridium difficile. Expert opinion on therapeutic patents 20101001
Fidaxomicin (OPT-80) for the treatment of Clostridium difficile infection. Expert opinion on pharmacotherapy 20100601
Clostridium difficile infection: update on emerging antibiotic treatment options and antibiotic resistance. Expert review of anti-infective therapy 20100501
Fidaxomicin: a new macrocyclic, RNA polymerase-inhibiting antibiotic for the treatment of Clostridium difficile infections. Future microbiology 20100401
Chinese medicine tongxinluo significantly lowers serum lipid levels and stabilizes vulnerable plaques in a rabbit model. Journal of ethnopharmacology 20090706
Lipiarmycin targets RNA polymerase and has good activity against multidrug-resistant strains of Mycobacterium tuberculosis. The Journal of antimicrobial chemotherapy 20081001
Properties