A macrolide antibiotic
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Virginiamycin M1

Item No. 9002172

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,4R,5E,10E,12E,14S)-8,9,14,15,24,25-hexahydro-14-hydroxy-4,12-3H-21,18-nitrilo-1H,22H-pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone
CAS Number
21411-53-0
Synonyms
  • Mikamycin A
  • NSC 244426
  • NSC 87432
  • Ostreogrycin A
  • Pristinamycin IIA
  • RP 12536
  • Streptogramin A
Molecular Formula
C28H35N3O7
Formula Weight
525.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: Slightly solubleMethanol: Slightly soluble
SMILES
O=C(/C=C/[C@@H](C)[C@@H](C(C)C)OC(C1=CCCN1C(C2=COC(C3)=N2)=O)=O)NC/C=C\C(C)=C\[C@@H](O)CC3=O
InChi Code
InChI=1S/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
InChi Key
DAIKHDNSXMZDCU-XWUZGEOZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    5 mg

    $347

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    25 mg

    $953

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    Cayman Chemical
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    Product Description

    Virginiamycin M1 is a macrolide antibiotic. It 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.1 They show good bactericidal activity against methicillin-resistant S. aureus (MRSA), although resistance in MRSA is conferred by the cfr gene.1,2 Virginiamycin M1 acts synergistically with virginiamycin S1 to irreversibly inhibit protein synthesis in bacteria.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fair, R.J., and Tor, Y. Antibiotics and bacterial resistance in the 21st century. Perspect. Medicin. Chem. 6, 25-64 (2014).

    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. 53(2), 779-781 (2009).

    3. Parfait, R., and Cocito, C. Lasting damage to bacterial ribosomes by reversibly bound virginiamycin M. Proc. Natl. Acad. Sci. USA 77(9), 5492-5496 (1980).