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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:
125-65-5
Molecular Weight:
378.50
EC Number:
204-747-5
UNSPSC Code:
12352200
PubChem Substance ID:
329825293
NACRES:
NA.77

Quality Level

100

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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H410

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)

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’.

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Thomas J K Findley et al.
Organic & biomolecular chemistry, 9(7), 2433-2451 (2011-02-18)
The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI(2)-mediated cyclisations. The strategy has been exploited in the first
Lykke H Hansen et al.
Antimicrobial agents and chemotherapy, 56(7), 3563-3567 (2012-05-02)
The cfr gene encodes the Cfr methyltransferase that methylates a single adenine in the peptidyl transferase region of bacterial ribosomes. The methylation provides resistance to several classes of antibiotics that include drugs of clinical and veterinary importance. This paper describes
Xinyang Wang et al.
Bioorganic & medicinal chemistry letters, 22(19), 6166-6172 (2012-08-31)
Owing to the increasingly serious problems caused by multidrug resistance in community-acquired infection pathogens, it has become an urgent need to develop new classes of antibiotics for overcoming the resistance. In this paper, we describe the design and synthesis of
Brigitte Malbruny et al.
Antimicrobial agents and chemotherapy, 55(4), 1470-1474 (2011-01-20)
Streptococcus agalactiae UCN70, isolated from a vaginal swab obtained in New Zealand, is resistant to lincosamides and streptogramins A (LS(A) phenotype) and also to tiamulin (a pleuromutilin). By whole-genome sequencing, we identified a 5,224-bp chromosomal extra-element that comprised a 1,479-bp
Helio S Sader et al.
The Journal of antimicrobial chemotherapy, 67(5), 1170-1175 (2012-01-31)
BC-3781 is an investigational semi-synthetic pleuromutilin antibiotic, which recently finished a clinical Phase 2 trial in acute bacterial skin and skin structure infections. BC-3781 binds to the 50S ribosomal subunit and cross-resistance with other antimicrobial classes is uncommon. We evaluated
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