Skip to Content
Merck
All Photos(1)

Documents

SML1750

Sigma-Aldrich

Fidaxomicin

≥95% (HPLC)

Synonym(s):

Clostomicin B1, Lipiarmycin A3, OPT 80, Tiacumicin B

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C52H74Cl2O18
CAS Number:
873857-62-6
Molecular Weight:
1058.04
MDL number:
MFCD27976367
UNSPSC Code:
12352200
PubChem Substance ID:
329826053
NACRES:
NA.77

biological source

(Actinoplanes deccanensis)

Quality Level

200

Assay

≥95% (HPLC)

form

powder

solubility

DMSO: soluble 1 mg/mL
chloroform: soluble 10 mg/mL
methanol: soluble 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

ClC1=C(CC)C(C(O[C@H]2[C@H](O)[C@H](OC)[C@H](OC/C3=C\C=C\C[C@H](O)/C(C)=C/[C@H](CC)[C@@H](O[C@]4([H])OC(C)(C)[C@@H](OC(C(C)C)=O)[C@H](O)[C@@H]4O)/C(C)=C/C(C)=C/C[C@]([C@H](O)C)([H])OC3=O)O[C@@H]2C)=O)=C(O)C(Cl)=C1O

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

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.
Therapeutic dosage of fidaxomicin is found have less bactericidal effect on the bowel microbiota and reduces the recurrence of C. difficile infection.

Other Notes

Chemical name: [(2R,3S,4S,5S,6R)-6-[[(3E,5E,8S,9Z,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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

M S Osburne et al.
Journal of virology, 33(3), 945-953 (1980-03-01)
We have used lipiarmycin, a specific inhibitor of initiation of transcription, to study the role of host RNA polymerase in the transcription programs of various phages of Bacillus subtilis. Unlike rifampin, lipiarmycin preferentially inhibits transcription dependent on the sigma subunit
Alan P Johnson
Current opinion in investigational drugs (London, England : 2000), 8(2), 168-173 (2007-03-03)
Optimer Pharmaceuticals Inc, in collaboration with Par Pharmaceutical Companies Inc, is developing OPT-80, a narrow-spectrum macrocyclic antibiotic secreted by the actinomycete Dactylosporangium aurantiacum, for the potential treatment of Clostridium difficile-associated diarrhea (CDAD) and vancomycin-resistant Enterococcus infection. A phase IIb/III clinical
A new macrocyclic antibiotic, fidaxomicin (OPT-80), causes less alteration to the bowel microbiota of Clostridium difficile-infected patients than does vancomycin.
Tannock G W, et al.
Microbiology, 156(11), 3354-3359 (2010)
Irina Artsimovitch et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 55 Suppl 2, S127-S131 (2012-07-07)
Fidaxomicin was recently approved for the treatment of Clostridium difficile infection. It inhibits transcription by bacterial RNA polymerase. Because transcription is a multistep process, experiments were conducted in which fidaxomicin was added at different stages of transcriptional initiation to identify
Farah Babakhani et al.
Antimicrobial agents and chemotherapy, 58(5), 2934-2937 (2014-02-20)
Fidaxomicin (FDX) is a narrow-spectrum antibiotic for the treatment of Clostridium difficile-associated diarrhea. While FDX and rifamycins share the same target (RNA polymerase), FDX exhibits a unique mode of action distinct from that of rifamycins. In comparative microbiological studies with
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service