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Merck
CN

SML1750

Fidaxomicin

From Actinoplanes deccanensis, ≥95% (HPLC), bacterial transcription inhibitor, powder

Synonym(s):

Clostomicin B1, Lipiarmycin A3, OPT 80, Tiacumicin B

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About This Item

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

Key Documents

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Product Name

Fidaxomicin, ≥95% (HPLC)

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 key

ZVGNESXIJDCBKN-UUEYKCAUSA-N

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

biological source

(Actinoplanes deccanensis)

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

Quality Level

200

Related Categories

Biochem/physiol Actions

Fidaxomicin is a first-in-class macrocyclic antibacterial agent for gram positive bacteria treatment, notably Clostridium difficile infections.
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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000457187
0000457187
0000212512
0000246807
0000246807

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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
M M Wösten
FEMS microbiology reviews, 22(3), 127-150 (1998-11-18)
The initiation of transcription is the most important step for gene regulation in eubacteria. To initiate transcription, RNA polymerase has to associate with a small protein, known as a sigma-factor. The sigma-factor directs RNA polymerase to a specific class of
Mutation in the Bacillus subtilis RNA polymerase beta' subunit confers resistance to lipiarmycin.
Maxime Gualtieri et al.
Antimicrobial agents and chemotherapy, 50(1), 401-402 (2005-12-27)
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)
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