125-65-5 Usage
Description
Pleuromutilin is an antibiotic substance produced by the basidiomycetes Pleurotus mutilus, a type of fungus. It is a diterpene with potent and highly selective activity against a range of Gram-positive bacteria, offering a unique mode of action with no cross-resistance to existing antibiotic classes. Pleuromutilin inhibits protein synthesis by binding to domain V of 23S rRNA, leading to the development of many semi-synthetic analogues as new generation antibiotics. It is a crystalline solid, known for its effectiveness in treating various infections.
Uses
Used in Veterinary Medicine:
Pleuromutilin is used as an antibiotic for treating swine infections, with semisynthetic pleuromutilins such as tiamulin and valnemulin being employed for this purpose.
Used in Human Medicine:
A semisynthetic pleuromutilin, retapamulin, has been introduced as a topical treatment for Gram-positive infections in humans.
Used in Antibacterial Agents:
Pleuromutilin is used as a potent and selective antibiotic agent for inhibiting the peptidyl transferase activity of the bacterial 50S ribosomal subunit by binding to the A site, thus preventing peptide bond formation and bacterial protein synthesis.
Used in Development of New Generation Antibiotics:
Pleuromutilin serves as a basis for the development of semi-synthetic analogues, which are part of the new generation of antibiotics, such as tiamulin and retapamulin, offering alternative treatment options for various bacterial infections.
references
[1]. kilaru s, collins cm, hartley aj, et al. establishing molecular tools for genetic manipulation of the pleuromutilin-producing fungus clitopilus passeckerianus. appl environ microbiol. 2009 nov;75(22):7196-204.[2]. long ks, hansen lh, jakobsen l, et al. interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center. antimicrob agents chemother. 2006 apr;50(4):1458-62.
Check Digit Verification of cas no
The CAS Registry Mumber 125-65-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 5 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 125-65:
(5*1)+(4*2)+(3*5)+(2*6)+(1*5)=45
45 % 10 = 5
So 125-65-5 is a valid CAS Registry Number.
InChI: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-/m0/s1
125-65-5Relevant articles and documents
SYNTHESE AB-TRANS-ANELLIERTER DERIVATE DES TRICYCLISCHEN DITERPENS PLEUROMUTILIN DURCH INTRAMOLEKULARE 1,5-HYDRID-VERSCHIEBUNG
Berner, H.,Schulz, G.,Schneider, H.
, p. 1807 - 1811 (1980)
The Diterpene Pleuromutilin(1) reacts with orthoformicacid-trimethylester at room temperature almost quantitatively to give the 11-keto-3-methylester 2 with AB-trans-configuration.This conversion is shown to occur through a 1,5-hydride-shift between C3 and C11.Treatment of 2 with Lewis acid (ZnCl2) initiated a retro-1,5-hydride-shift which resulted in the formation of Pleuromutilin(1).Mechanistic aspects and structure assignments, which are based on chemical and spectroscopic ((1)H- and (13)C-NMR) data are discussed.
