Pleuromutilin

Names

[ CAS No. ]:
125-65-5

[ Name ]:
Pleuromutilin

[Synonym ]:
Acetic acid, 2-hydroxy-, 6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester
Pleuromulin
Valnemulin impurity E
5-Hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate
Drosophilin B,Mutilin 14-glycolate
EINECS 204-747-5
3-Hydroxy-2,4,7,14-tetramethyl-9-oxo-4-vinyltricyclo[5.4.3.0]tetradec-6-yl glycolate

Biological Activity

[Description]:

pleuromutilin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of bacteria.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Shang RF et al. Synthesis and biological evaluation of new pleuromutilin derivatives as antibacterial agents. Molecules. 2014 Nov 19;19(11):19050-65.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
482.8±45.0 °C at 760 mmHg

[ Melting Point ]:
170-171ºC

[ Molecular Formula ]:
C₂₂H₃₄O₅

[ Molecular Weight ]:
378.502

[ Flash Point ]:
158.7±22.2 °C

[ Exact Mass ]:
378.240631

[ PSA ]:
83.83000

[ LogP ]:
2.63

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.538

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MC5408000

CHEMICAL NAME :: Glycolic acid, 8-ester with octahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-vinyl- 3a,9- propano-3aH-cyclopentacycloocten-1(4H)-one

CAS REGISTRY NUMBER :: 125-65-5

LAST UPDATED :: 199806

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H34-O5

MOLECULAR WEIGHT :: 378.56

WISWESSER LINE NOTATION :: T568/EN 2AE N BV EXTJ H1 I1 JOV1Q L1U1 L1 MQ N1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 6,123,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 6,123,1981

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
MC5408000

[ HS Code ]:
2918199090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2918199090

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

Articles

Novel ABC transporter gene, vga(C), located on a multiresistance plasmid from a porcine methicillin-resistant Staphylococcus aureus ST398 strain.

Antimicrob. Agents Chemother. 53 , 3589-91, (2009)

A novel ABC transporter gene, vga(C), was identified on the 14,365-bp multiresistance plasmid pKKS825 in a porcine methicillin (meticillin)-resistant Staphylococcus aureus isolate of sequence type 398...

Design, synthesis, and antibacterial activity of novel pleuromutilin derivatives bearing an amino thiazolyl ring.

Arch. Pharm. (Weinheim) 345(8) , 638-46, (2012)

A series of novel pleuromutilin derivatives containing the amino thiazolyl ring were designed, synthesized, and evaluated for their antibacterial activities in vitro against Gram-positive clinical bac...

Single 23S rRNA mutations at the ribosomal peptidyl transferase centre confer resistance to valnemulin and other antibiotics in Mycobacterium smegmatis by perturbation of the drug binding pocket.

Mol. Microbiol. 71(5) , 1218-27, (2009)

Tiamulin and valnemulin target the peptidyl transferase centre (PTC) on the bacterial ribosome. They are used in veterinary medicine to treat infections caused by a variety of bacterial pathogens, inc...