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Merck

SML0285

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
PubChem Substance ID:
329825293
UNSPSC Code:
12352200
NACRES:
NA.77
EC Number:
204-747-5

Key Documents

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InChI key

ZRZNJUXESFHSIO-BKUNHTPHSA-N

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

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

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

Quality Level

100

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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.
Pleuromutilin is an antibiotic natural product that inhibits bacterial protein synthesis.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H410

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000103768
0000035366
074M4737V
032M4709V

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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)
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
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
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
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