21411-53-0 Usage
Description
VIRGINIAMYCIN M1, also known as Ostreogrycin A or Streptogramin A, is a macrocyclic lactone antibiotic that is a major component of the virginiamycin complex. It is a light yellow powder and exhibits bactericidal activity against Gram-positive organisms, including methicillin-resistant Staphylococcus aureus (MRSA). VIRGINIAMYCIN M1 acts synergistically with structurally unrelated cyclic depsipeptides, such as virginiamycin B (Ostreogrycin B, Streptogramin B) and virginiamycin S, to inhibit peptide elongation by blocking the formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA.
Uses
Used in Pharmaceutical Industry:
VIRGINIAMYCIN M1 is used as an antibiotic for its high activity against Gram-positive bacteria, particularly MRSA. It is employed in combination with other cyclic depsipeptides to enhance its antibacterial properties and combat antibiotic resistance.
Used in Agricultural Industry:
VIRGINIAMYCIN M1 is used as a growth promotant to improve the health and growth of livestock. Its antibacterial properties help prevent infections and promote overall well-being in animals, leading to better growth rates and productivity.
Biological Activity
virginiamycin m1 is a macrolide antibiotic that reversibly inhibits protein synthesis [1][2][3].virginiamycin complex contains two antibiotics, virginiamycin m1 and virginiamycin s1. streptogramins are divided into class a and class b based on their structures. virginiamycin m1, also known as streptogramin a, is a member of the streptogramin a group of antibiotics, which bind the 50s ribosomal subunit at the peptidyl transferase center to inhibit initiation and translocation. they show good bactericidal activity against methicillin-resistant s. aureus (mrsa), although resistance in mrsa is conferred by the cfr gene. virginiamycin m1 has activity against gram-positive and in select cases gram-negative bacteria. combination of group a and b streptogramins exhibit bactericidal activity [1]. virginiamycin m1 acted synergistically with virginiamycin s1 to irreversibly inhibit protein synthesis in bacteria. in cell-free systems, virginiamycin m1 and virginiamycin s1 bound to the large ribosomal subunit, and the affinity of ribosomes for vs is increased by vm [2][3].
Contact allergens
Pristinamycin is a systemic antibiotic of the synergistins/
streptogramins class, composed of two subunits: pristinamycin
IA and pristinamycin IIA. It induces several
types of drug reactions such as maculo-papular exanthema,
systemic dermatitis, or acute generalized exanthematous
pustulosis. Some patients have been previously
skin-sensitized by virginiamycin. Crossreactivity
is expected to virginiamycin and to the associated dalfopristin
and quinupristin.
references
[1]. fair rj, tor y. antibiotics and bacterial resistance in the 21st century. perspect medicin chem. 2014 aug 28;6:25-64.[2]. kehrenberg c, cuny c, strommenger b, et al. methicillin-resistant and -susceptible staphylococcus aureus strains of clonal lineages st398 and st9 from swine carry the multidrug resistance gene cfr. antimicrob agents chemother. 2009 feb;53(2):779-81.[3]. parfait r, cocito c. lasting damage to bacterial ribosomes by reversibly bound virginiamycin m. proc natl acad sci u s a. 1980 sep;77(9):5492-6.
Check Digit Verification of cas no
The CAS Registry Mumber 21411-53-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,4,1 and 1 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 21411-53:
(7*2)+(6*1)+(5*4)+(4*1)+(3*1)+(2*5)+(1*3)=60
60 % 10 = 0
So 21411-53-0 is a valid CAS Registry Number.
InChI:InChI=1/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5+,10-9+,18-13+/t19-,20-,26-/m1/s1
21411-53-0Relevant articles and documents
Synergy of streptogramin antibiotics occurs independently of their effects on translation
Noeske, Jonas,Huang, Jian,Olivier, Nelson B.,Giacobbe, Robert A.,Zambrowski, Mark,Cate, Jamie H. D.
, p. 5269 - 5279 (2014)
Streptogramin antibiotics are divided into types A and B, which in combination can act synergistically. We compared the molecular interactions of the streptogramin combinations Synercid (type A, dalfopristin; type B, quinupristin) and NXL 103 (type A, flopristin; type B, linopristin) with the Escherichia coli 70S ribosome by X-ray crystallography. We further analyzed the activity of the streptogramin components individually and in combination. The streptogramin A and B components in Synercid and NXL 103 exhibit synergistic antimicrobial activity against certain pathogenic bacteria. However, in transcription-coupled translation assays, only combinations that include dalfopristin, the streptogramin A component of Synercid, show synergy. Notably, the diethylaminoethylsulfonyl group in dalfopristin reduces its activity but is the basis for synergy in transcription-coupled translation assays before its rapid hydrolysis from the depsipeptide core. Replacement of the diethylaminoethylsulfonyl group in dalfopristin by a nonhydrolyzable group may therefore be beneficial for synergy. The absence of general streptogramin synergy in transcription-coupled translation assays suggests that the synergistic antimicrobial activity of streptogramins can occur independently of the effects of streptogramin on translation. Copyright
Modular, Scalable Synthesis of Group A Streptogramin Antibiotics
Li, Qi,Seiple, Ian B.
, p. 13304 - 13307 (2017/10/05)
Streptogramin antibiotics are used clinically to treat multidrug-resistant bacterial infections, but their poor physicochemical properties and narrow spectra of activity have limited their utility. New methods to chemically modify streptogramins would enable structural optimization to overcome these limitations as well as to combat growing resistance to the class. Here we report a modular, scalable synthesis of group A streptogramin antibiotics that proceeds in 6-8 linear steps from simple chemical building blocks. We have applied our route to the synthesis of four natural products in this class including two that have never before been accessed by fully synthetic routes. We anticipate that this work will lead to the discovery of new streptogramin antibiotics that overcome previous limitations of the class.
