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MedKoo Cat#: 571120 | Name: Pleuromulin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pleuromulin is an antibiotic that derives from a class of antibacterials with different mechanisms of action from clinically used antibacterials. It has been shown that there is rarely cross-resistance between pleuromutilin derivatives and other antimicrobial agents.

Chemical Structure

Pleuromulin
Pleuromulin
CAS#125-65-5

Theoretical Analysis

MedKoo Cat#: 571120

Name: Pleuromulin

CAS#: 125-65-5

Chemical Formula: C22H34O5

Exact Mass: 378.2406

Molecular Weight: 378.51

Elemental Analysis: C, 69.81; H, 9.05; O, 21.13

Price and Availability

Size Price Availability Quantity
25mg USD 550.00
50mg USD 950.00
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Related CAS #
No Data
Synonym
Pleuromulin; A 4014C; A-4014C; A4014C; NSC 121145; Drosopholin B; Pleuromutilin
IUPAC/Chemical Name
Acetic acid, hydroxy-, 6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester, (3aS-(3aalpha,4beta,5alpha,6alpha,8beta,9alpha,9abeta,10S*))- (9CI)
InChi Key
ZRZNJUXESFHSIO-FEOSZSLTSA-N
InChi Code
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 Code
O=C(O[C@H]1[C@]([C@H](C)CC2)(C)[C@@](C(CC3)=O)([H])[C@@]32[C@@H](C)[C@H](O)[C@](C)(C=C)C1)CO
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 378.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Tang YZ, Liu YH, Chen JX. Pleuromutilin and its derivatives-the lead compounds for novel antibiotics. Mini Rev Med Chem. 2012 Jan;12(1):53-61. Review. PubMed PMID: 22070694. 2: Rugna G, Bonilauri P, Carra E, Bergamini F, Luppi A, Gherpelli Y, Magistrali CF, Nigrelli A, Alborali GL, Martelli P, La T, Hampson DJ, Merialdi G. Sequence types and pleuromutilin susceptibility of Brachyspira hyodysenteriae isolates from Italian pigs with swine dysentery: 2003-2012. Vet J. 2015 Jan;203(1):115-9. doi: 10.1016/j.tvjl.2014.10.033. Epub 2014 Nov 7. PubMed PMID: 25486860. 3: Li J, Li B, Wendlandt S, Schwarz S, Wang Y, Wu C, Ma Z, Shen J. Identification of a novel vga(E) gene variant that confers resistance to pleuromutilins, lincosamides and streptogramin A antibiotics in staphylococci of porcine origin. J Antimicrob Chemother. 2014 Apr;69(4):919-23. doi: 10.1093/jac/dkt482. Epub 2013 Dec 8. PubMed PMID: 24324222. 4: van Duijkeren E, Greko C, Pringle M, Baptiste KE, Catry B, Jukes H, Moreno MA, Pomba MC, Pyörälä S, Rantala M, Ružauskas M, Sanders P, Teale C, Threlfall EJ, Torren-Edo J, Törneke K. Pleuromutilins: use in food-producing animals in the European Union, development of resistance and impact on human and animal health. J Antimicrob Chemother. 2014 Aug;69(8):2022-31. doi: 10.1093/jac/dku123. Epub 2014 May 3. Review. PubMed PMID: 24793902. 5: Shang R, Wang J, Guo W, Liang J. Efficient antibacterial agents: a review of the synthesis, biological evaluation and mechanism of pleuromutilin derivatives. Curr Top Med Chem. 2013;13(24):3013-25. Review. PubMed PMID: 24200363. 6: Hicklin RW, López Silva TL, Hergenrother PJ. Synthesis of bridged oxafenestranes from pleuromutilin. Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9880-3. doi: 10.1002/anie.201404765. Epub 2014 Jul 17. PubMed PMID: 25045118. 7: Liu H, Xiao S, Zhang D, Mu S, Zhang L, Wang X, Xue F. Synthesis and Antibacterial Activity of Novel Pleuromutilin Derivatives. Biol Pharm Bull. 2015;38(7):1041-8. doi: 10.1248/bpb.b15-00123. PubMed PMID: 26133714. 8: Yi Y, Yang G, Zhang C, Chen J, Liang J, Shang R. Synthesis and evaluation of novel pleuromutilin derivatives with a substituted pyrimidine moiety. Eur J Med Chem. 2015 Aug 28;101:179-84. doi: 10.1016/j.ejmech.2015.06.034. Epub 2015 Jun 22. PubMed PMID: 26134552. 9: Chen L, Yang D, Pan Z, Lai L, Liu J, Fang B, Shi S. Synthesis and Antimicrobial Activity of the Hybrid Molecules between Sulfonamides and Active Antimicrobial Pleuromutilin Derivative. Chem Biol Drug Des. 2015 Aug;86(2):239-45. doi: 10.1111/cbdd.12486. Epub 2014 Dec 18. PubMed PMID: 25431015. 10: Wendlandt S, Kadlec K, Feßler AT, Schwarz S. Identification of ABC transporter genes conferring combined pleuromutilin-lincosamide-streptogramin A resistance in bovine methicillin-resistant Staphylococcus aureus and coagulase-negative staphylococci. Vet Microbiol. 2015 Jun 12;177(3-4):353-8. doi: 10.1016/j.vetmic.2015.03.027. Epub 2015 Apr 8. PubMed PMID: 25891423. 11: Dong YJ, Meng ZH, Mi YQ, Zhang C, Cui ZH, Wang P, Xu ZB. Synthesis of novel pleuromutilin derivatives. Part 1: preliminary studies of antituberculosis activity. Bioorg Med Chem Lett. 2015 Apr 15;25(8):1799-1803. doi: 10.1016/j.bmcl.2015.02.023. Epub 2015 Feb 17. PubMed PMID: 25736994. 12: Fazakerley NJ, Helm MD, Procter DJ. Total synthesis of (+)-pleuromutilin. Chemistry. 2013 May 17;19(21):6718-23. doi: 10.1002/chem.201300968. Epub 2013 Apr 15. PubMed PMID: 23589420. 13: Hillen S, Willems H, Herbst W, Rohde J, Reiner G. Mutations in the 50S ribosomal subunit of Brachyspira hyodysenteriae associated with altered minimum inhibitory concentrations of pleuromutilins. Vet Microbiol. 2014 Aug 6;172(1-2):223-9. doi: 10.1016/j.vetmic.2014.04.021. Epub 2014 May 5. PubMed PMID: 24948419. 14: Novak R. Are pleuromutilin antibiotics finally fit for human use? Ann N Y Acad Sci. 2011 Dec;1241:71-81. doi: 10.1111/j.1749-6632.2011.06219.x. Review. PubMed PMID: 22191527. 15: Dreier I, Kumar S, Søndergaard H, Rasmussen ML, Hansen LH, List NH, Kongsted J, Vester B, Nielsen P. A click chemistry approach to pleuromutilin derivatives, part 2: conjugates with acyclic nucleosides and their ribosomal binding and antibacterial activity. J Med Chem. 2012 Mar 8;55(5):2067-77. doi: 10.1021/jm201266b. Epub 2012 Feb 16. PubMed PMID: 22280300. 16: Wang XY, Chen M, Wang D, Chen XD, Ling Y, Wang XL, Wang H. [Synthesis and biological evaluation of novel pleuromutilin derivatives with nitrogen-containing heterocycles as antibacterial agents]. Yao Xue Xue Bao. 2015 Oct;50(10):1297-304. Chinese. PubMed PMID: 26837177. 17: Bailey AM, Alberti F, Kilaru S, Collins CM, de Mattos-Shipley K, Hartley AJ, Hayes P, Griffin A, Lazarus CM, Cox RJ, Willis CL, O'Dwyer K, Spence DW, Foster GD. Identification and manipulation of the pleuromutilin gene cluster from Clitopilus passeckerianus for increased rapid antibiotic production. Sci Rep. 2016 May 4;6:25202. doi: 10.1038/srep25202. PubMed PMID: 27143514; PubMed Central PMCID: PMC4855138. 18: Li B, Wendlandt S, Yao J, Liu Y, Zhang Q, Shi Z, Wei J, Shao D, Schwarz S, Wang S, Ma Z. Detection and new genetic environment of the pleuromutilin-lincosamide-streptogramin A resistance gene lsa(E) in methicillin-resistant Staphylococcus aureus of swine origin. J Antimicrob Chemother. 2013 Jun;68(6):1251-5. doi: 10.1093/jac/dkt015. Epub 2013 Feb 5. PubMed PMID: 23386262. 19: Dreier I, Hansen LH, Nielsen P, Vester B. A click chemistry approach to pleuromutilin derivatives. Part 3: extended footprinting analysis and excellent MRSA inhibition for a derivative with an adenine phenyl side chain. Bioorg Med Chem Lett. 2014 Feb 15;24(4):1043-6. doi: 10.1016/j.bmcl.2014.01.019. Epub 2014 Jan 15. PubMed PMID: 24486133. 20: Murphy SK, Zeng M, Herzon SB. A modular and enantioselective synthesis of the pleuromutilin antibiotics. Science. 2017 Jun 2;356(6341):956-959. doi: 10.1126/science.aan0003. PubMed PMID: 28572392.