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Key Documents

SML0285

Sigma-Aldrich

Pleuromutilin

≥95%

Synonym(s):

Drosophilin B, Mutilin 14-glycolate, NSC 121145

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About This Item

Empirical Formula (Hill Notation):
C22H34O5
CAS Number:
Molecular Weight:
378.50
EC Number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥95%

form

powder

optical activity

[α]/D +30 to +40° (c=1; CH2Cl2)

color

white to beige

solubility

DMSO: >10 mg/mL (warmed)

shipped in

wet ice

storage temp.

−20°C

SMILES string

C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CO

InChI

1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21+,22+/m1/s1

InChI key

ZRZNJUXESFHSIO-BKUNHTPHSA-N

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Biochem/physiol Actions

Pleuromutilin is a diterpene that acts against gram positive bacteria and mycoplasm. It is present in Pleurotus mutilus and Pleurotus passecherianus. Pleuromutilin exhibits its antibacterial action by interfering with the prokaryotic 70S ribosomal subunit and inactivates initiation complex. Pleuromutilin is useful in treating mycoplasma infections in animals.
Pleuromutilin is an antibiotic natural product that inhibits bacterial protein synthesis by binding to bacterial ribosomes in the peptidyl transferase center and inhibiting peptide bond formation.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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The enterococcal ABC transporter gene lsa(E) confers combined resistance to lincosamides, pleuromutilins and streptogramin A antibiotics in methicillin-susceptible and methicillin-resistant Staphylococcus aureus.
Sarah Wendlandt et al.
The Journal of antimicrobial chemotherapy, 68(2), 473-475 (2012-10-11)
A dialdehyde cyclization cascade: an approach to pleuromutilin.
Matthew D Helm et al.
Angewandte Chemie (International ed. in English), 48(49), 9315-9317 (2009-11-11)
Izabela Karpiuk et al.
Przeglad epidemiologiczny, 66(4), 567-573 (2012-01-01)
Development of new mechanisms of resistance and relatively easy and fast transferring of resistance genes between cells have resulted in emergence of large number of multi-drug resistant bacteria in recent years. Therefore, it is important to intensively search for new
James E Ross et al.
Journal of clinical microbiology, 50(10), 3361-3364 (2012-07-21)
MIC and disk diffusion quality control (QC) ranges were established for two new pleuromutilin antimicrobials (BC-3205 and BC-3781) in an eight-laboratory study performed according to Clinical and Laboratory Standards Institute M23-A3 guidelines. Staphylococcus aureus ATCC 29213 and 25923, Streptococcus pneumoniae
Junjia Liu et al.
Chemical communications (Cambridge, England), 47(5), 1500-1502 (2010-11-17)
Two syntheses of the tricyclic carbon skeleton of pleuromutilin are reported. Diastereoselective 1,4-conjugate additions were used to elaborate bicyclic precursors at an early stage of each route, while ring-forming olefin metatheses were executed to complete the pleuromutilin carbon framework. The

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