| Identification | Back Directory | [Name]
Virginiamycin S1 | [CAS]
23152-29-6 | [Synonyms]
Antibiotic 899
Staphylomycin S
Virginiamycin S1
Verginiamycin S1
Antibiotic 1754Z3B
VirginiaMycin coMplex
Antibiotic 899, Staphylomycin S
StaphyloMycin S, PA 114B2, 899, A1745Z3B, Factor S
N-[(3-Hydroxy-2-pyridinyl)carbonyl]cyclo[L-Thr*-D-Abu-L-Pro-N-methyl-L-Phe-4-oxo-L-pipecoloyl-L-phenyl Gly-]
N-[(3-Hydroxy-2-pyridyl)carbonyl]cyclo(L-Thr*-D-Abu-L-Pro-N-methyl-L-Phe-4-oxo-L-2-piperidinecarbonyl-L-phenyl Gly-)
Cebin V, Eskalin V, EskaMicin, Stafac, StephyloMycin, MikaMycin, Ostreogrycin, Patricin, PristinaMycin, StreptograMin, VernaMycin. | [EINECS(EC#)]
245-462-6 | [Molecular Formula]
C43H49N7O10 | [MDL Number]
MFCD00864857 | [MOL File]
23152-29-6.mol | [Molecular Weight]
823.899 |
| Chemical Properties | Back Directory | [Melting point ]
240-242° | [alpha ]
D20 -28° (c = 1 in ethanol) | [storage temp. ]
?20°C | [solubility ]
methanol: soluble5mg/mL | [form ]
powder | [color ]
white | [Contact allergens]
Like the other streptogramin, pristinamycin, virginiamycin
is made of two subunits, virginiamycin S1 and
virginiamycin M1. Dermatitis was quite common in
people using the formerly available topical virginiamycin.
Occupational dermatitis was observed in the
pharmaceutical industry, in breeders, and in a surgeon
who used topical virginiamycin on postoperative
wounds (personal observation). |
| Hazard Information | Back Directory | [Uses]
Virginiamycin complex is defined as a mixture of 75% ostreogrycin A (virginamycin M1) and 25% virginiamycin S1, together with the less abundant S analogues. As the two major components have quite different solubilities, these proportions are not readily achieved or used. BioAustralis has isolated and re-combined the individual components to provide the defined components of virginiamycin complex. The composition of the complex is important as Virginiamycin S1 acts a synergist, binding to the conformational change of the peptidyl transferase centre of the 50S ribosome induced by ostreogrycin A. | [Uses]
Virginiamycin S1 is one of a family of depsipeptide antibiotics co-produced with ostreogrycin A and used as a synergistic mixture. Virginiamycin S1, also known as Staphylomycin S and Factor S among other synonyms, was discovered independently and named by several groups, leading to considerable confusion in the literature. Virginiamycin S1 acts a synergist, binding to the conformational change of the peptidyl transferase centre of the 50S ribosome induced by ostreogrycin A. Virginiamycin S1 differs from virginiamycin B in lacking the dimethylamino moiety on the phenyl ring. | [Biological Activity]
virginiamycin s1 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 s1 is a member of the streptogramin b group of antibiotics, which bind the peptide exit tunnel to inhibit the elongation stage of translation. 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 s1 acted synergistically with virginiamycin m1 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]. | [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. |
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