Structural Formula Vector Image
Title: Virginiamycin
CAS Registry Number: 11006-76-1
Additional Names: Staphylomycin; virgimycin
Manufacturers' Codes: SKF-7988
Trademarks: Eskalin (SKB); Stafac (SKB); Staphylomycine (SKB)
Literature References: One of the streptogramins, q.v., produced by a Streptomyces virginiae: P. De Somer, P. Van Dijck, Antibiot. Chemother. 5, 632 (1955). Two principal components S1 and M1. Separation of factors M and S: H. Vanderhaeghe et al., ibid. 7, 606 (1957); of the complex into six components: Gosselinckx, Parmentier, Chromatogr. Symp., 2nd 1962, 1817. Nomenclature and identification with other streptogramins: P. Crooy, R. De Neys, J. Antibiot. 25, 371 (1972). HPLC determn in animal feeds: F. Gossele et al., Analyst 116, 1373 (1991). Quantitative determn of components from fermentation broth: B. V. Tyaglov et al., J. Planar Chromatogr. Mod. TLC 8, 374 (1995). Mode of action: B. T. Porse, R. A. Garrett, J. Mol. Biol. 286, 375 (1999). Review: A. M. Biot, Drugs Pharm. Sci. 22, 695-720 (1984). Review of use in feed: W. Witte et al., Acta Vet. Scand. Suppl. 93, 37-45 (2000).
Properties: Amorphous, reddish-yellow powder, mp 115-120°. Sol in methanol, ethanol, chloroform. Poorly sol in water. Practically insol in hexane and petroleum ether.
Melting point: mp 115-120°
Derivative Type: Virginiamycin S1
CAS Registry Number: 23152-29-6
Additional Names: Staphylomycin S
Molecular Formula: C43H49N7O10
Molecular Weight: 823.89
Percent Composition: C 62.69%, H 5.99%, N 11.90%, O 19.42%
Literature References: Hexacyclicdepsipeptide antibiotic. Structure: H. Vanderhaeghe, G. Parmentier, J. Am. Chem. Soc. 82, 4414 (1960).
Properties: Crystals from methanol, mp 240-242°. [a]D20 -28° (c = 1 in ethanol). uv max (ethanol): 305 nm (log e 3.85).
Melting point: mp 240-242°
Optical Rotation: [a]D20 -28° (c = 1 in ethanol)
Absorption maximum: uv max (ethanol): 305 nm (log e 3.85)
Derivative Type: Virginiamycin M1
CAS Registry Number: 21411-53-0
Additional Names: Mikamycin A; ostreogrycin A; pristinamycin IIA; staphylomycin M1; streptogramin A; vernamycin A
Molecular Formula: C28H35N3O7
Molecular Weight: 525.59
Percent Composition: C 63.99%, H 6.71%, N 7.99%, O 21.31%
Literature References: Macrolactone antibiotic, see also Pristinamycin. Structure: G. R. Delpierre et al., Tetrahedron Lett. 1966, 369; eidem, J. Chem. Soc. C 1966, 1653; D. G. I. Kingston et al., ibid. 1669. Biosynthesis: idem et al., Rev. Latinoam. Quim. 20, 128 (1989). Molecular dynamics: E. Surcouf et al., Stud. Phys. Theor. Chem. 71, 719 (1990).
Properties: Colorless laths from ethyl acetate, mp 203-205°. [a]D20 -218° ( c = 0.34 in ethanol). uv max (ethanol): 228 nm (log e 4.51).
Melting point: mp 203-205°
Optical Rotation: [a]D20 -218° ( c = 0.34 in ethanol)
Absorption maximum: uv max (ethanol): 228 nm (log e 4.51)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial; growth promotant.
Keywords: Antibacterial (Antibiotics).

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