Pleuromutilin

Pleuromutilin
Names

IUPAC name (4R,5S,6S,8R,9aR,10R)-6-Ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate
Identifiers
CAS Number	125-65-5^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL497295^N
ChemSpider	8061754^N
ECHA InfoCard	100.004.316
KEGG	C09169^N
PubChem	9886081
UNII	3DE4A80MZ1^N
InChI 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^N Key: ZRZNJUXESFHSIO-BKUNHTPHSA-N^N InChI=1/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 Key: ZRZNJUXESFHSIO-BKUNHTPHBC
SMILES C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CO)C
Properties
Chemical formula	C₂₂H₃₄O₅
Molar mass	378.509 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Pleuromutilin and its derivatives are antibacterial drugs that inhibit protein synthesis in bacteria by binding to the peptidyl transferase component of the 50S subunit of ribosomes.^[1]^[2]

This class of antibiotics includes the licensed drugs retapamulin (approved for topical use in humans), valnemulin and tiamulin (approved for use in animals) and the investigational drugs azamulin and lefamulin (BC-3781).

History

Pleuromutilin was first discovered as an antibiotic in 1950.^[3] It is derived from the fungus Clitopilus passeckerianus (formerly Pleurotus passeckerianus), and has also been found in Drosophila subatrata, Clitopilus scyphoides, and some other Clitopilus species.^[4]

References

↑ Long, Katherine S; Lykke H. Hansen; Lene Jakobsen; Birte Vester (April 2006). "Interaction of Pleuromutilin Derivatives with the Ribosomal Peptidyl Transferase Center" (PDF). Antimicrobial Agents and Chemotherapy. 50 (4): 1458–1462. doi:10.1128/AAC.50.4.1458-1462.2006. PMC 1426994. PMID 16569865.
↑ Lolk, L.; Pøhlsgaard, J.; Jepsen, A. S.; Hansen, L. H.; Nielsen, H.; Steffansen, S. I.; Sparving, L.; Nielsen, A. B.; Vester, B.; Nielsen, P. (2008). "A Click Chemistry Approach to Pleuromutilin Conjugates with Nucleosides or Acyclic Nucleoside Derivatives and Their Binding to the Bacterial Ribosome". Journal of Medicinal Chemistry. 51 (16): 4957–4967. doi:10.1021/jm800261u. PMID 18680270.
↑ Novak, R; Shlaes DM (February 2010). "The pleuromutilin antibiotics: a new class for human use". Current Opinion in Investigational Drugs. 11 (2): 182–91. PMID 20112168.
↑ Kilaru, Sreedhar; Catherine M. Collins; Amanda J. Hartley; Andy M. Bailey; Gary D. Foster (2009-09-18). "Establishing Molecular Tools for Genetic Manipulation of the Pleuromutilin-Producing Fungus Clitopilus passeckerianus". Appl Environ Microbiol. American Society for Microbiology. 75 (22): 7196–7204. doi:10.1128/AEM.01151-09. PMC 2786515. PMID 19767458.

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Plazomicin^† Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

Fluorocyclines	Eravacycline^†

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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