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SML1750

Fidaxomicin

Name: Fidaxomicin
Brand: SIGMA

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

Assay:

≥95% (HPLC)

Form:

powder

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Properties

Product Name

Fidaxomicin, ≥95% (HPLC)

biological source

(Actinoplanes deccanensis)

Quality Segment

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

Description

Biochem/physiol Actions

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

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.

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