| Identification | Back Directory | [Name]
VIRGINIAMYCIN M1 | [CAS]
21411-53-0 | [Synonyms]
C11299
PA 114A
Factor M
NSC 87432
NSC 244426
MIKAMYCIN A
Vernamycin A
AVirginiaMyci
STAPHYLOMYCIN
VIRGINIAMYCINE
Ostreogrycin A
Streptogramin A
Staphylomycin M1
VIRGINIAMYCIN M1
Pristinamycin II
Pristinamycin IIA
Antibiotic PA 114A
Antibiotic PA-114A1
Factor M (antibiotic)
VirginiaMycin M1 (90%)
(3R,4R,5E,10E,12E,14S)-
MikamycinA, Staphylomycin
VirginiaMycin M1
DISCONTINUED
VirginiaMycin M1, froM StreptoMyces virginiae
Virginiamycin M1, 98%, from Streptomyces virginiae
Verginiamycin M1 Ostreogrycin A Antibiotic PA 114A NSC 244426 NSC 87432
MikaMycin A, PristinaMycin IIA, StephyloMycin M1, StreptograMin A, Syncothrecin A, Synergistin A1, VirginiaMycin M1, VernaMycin A, 14752-2, E129A, PA 114A, 1745Z3A, 547C, Factor M | [EINECS(EC#)]
244-376-6 | [Molecular Formula]
C28H35N3O7 | [MDL Number]
MFCD00869411 | [MOL File]
21411-53-0.mol | [Molecular Weight]
525.59 |
| Chemical Properties | Back Directory | [Melting point ]
165-167℃ | [alpha ]
D20 -218° ( c = 0.34 in ethanol) | [Boiling point ]
825.2±65.0 °C(Predicted) | [density ]
1.26±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
chloroform/methanol: soluble10mg/mL | [form ]
powder | [pka]
13.18±0.70(Predicted) | [color ]
yellow to tan | [Stability:]
Light Sensitive | [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. | [InChIKey]
DAIKHDNSXMZDCU-QHKJSJJMSA-N | [SMILES]
CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow powder | [Uses]
Macrolactone antibiotic. Antibacterial; growth promotant. | [Uses]
Ostreogrycin A (virginiamycin M1, streptogramin A) is the major component of the virginamycin complex. In the 1950s this complex was independently discovered so many times that the literature became highly confusing. Ostreogrycin A is a macrocyclic lactone antibiotic that acts synergistically with the structurally unrelated cyclic depsipeptides, virginiamycin B (ostreogrycin B, streptogramin B) and virginiamycin S, to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Ostreogrycin A is highly active against Gram positive bacteria, particularly MRSA. | [Uses]
Ostreogrycin A (virginiamycin M1, streptogramin A) is the major component of the virginiamycin complex. In the 1950s this complex was independently discovered so many times that the literature became highly confusing. Ostreogrycin A is a macrocyclic lactone antibiotic that acts synergistically with the structurally unrelated cyclic depsipeptides, virginiamycin B (ostreogrycin B, streptogramin B) and virginiamycin S, to inhibit peptide elongation. This is achieved by blocking formation of a peptide bond between the growing peptide chain (peptidyl-tRNA) linked to the 50S ribosome and aminoacyl-tRNA. Ostreogrycin A is highly active against Gram positive bacteria, particularly MRSA. | [Definition]
ChEBI: A macrolide that is (together with pristinamycin IA) a component of pristinamycin, an oral streptogramin antibiotic produced by Streptomyces pristinaespiralis. Pristinamycin exhibits bactericidal activity against Gram positive organisms includ
ng methicillin-resistant Staphylococcus aureus. | [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]. | [storage]
Store at -20°C | [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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