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Merck
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資料

安全性情報

SML1750

Sigma-Aldrich

Fidaxomicin

≥95% (HPLC)

別名:

Clostomicin B1, Lipiarmycin A3, OPT 80, Tiacumicin B

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About This Item

実験式（ヒル表記法）:
C52H74Cl2O18
CAS番号:
873857-62-6
分子量:
1058.04
MDL番号:
MFCD27976367
UNSPSCコード:
12352200
PubChem Substance ID:
329826053
NACRES:
NA.77

由来生物

(Actinoplanes deccanensis)

品質水準

200

アッセイ

≥95% (HPLC)

形状

powder

溶解性

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

輸送温度

ambient

保管温度

2-8°C

SMILES記法

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

生物化学的／生理学的作用

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.

その他情報

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

保管分類コード

11 - Combustible Solids

WGK

WGK 3

引火点(°F)

Not applicable

引火点(℃)

Not applicable

適用法令

試験研究用途を考慮した関連法令を主に挙げております。化学物質以外については、一部の情報のみ提供しています。 製品を安全かつ合法的に使用することは、使用者の義務です。最新情報により修正される場合があります。WEBの反映には時間を要することがあるため、適宜SDSをご参照ください。

Jan Code

SML1750-BULK:
SML1750-VAR:
SML1750-1MG-PW:
SML1750-1MG:

試験成績書（COA）

製品のロット番号・バッチ番号を入力して、試験成績書（COA） を検索できます。ロット番号・バッチ番号は、製品ラベルに「Lot」または「Batch」に続いて記載されています。

以前この製品を購入いただいたことがある場合

文書ライブラリで、最近購入した製品の文書を検索できます。

文書ライブラリにアクセスする

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
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
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
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
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
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Human Microbiome Research Workflow: An Overview of the Role in Human Health and Disease

An overview of human microbiome research, workflow challenges, sequencing, library production, data analysis, and available microbiome reagents to support your research.

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