Rosaramicin

Title: Rosaramicin
CAS Registry Number: 35834-26-5
CAS Name: 4¢-Deoxycirramycin A1
Additional Names: 3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-9-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranosyl]oxy]-4,17-dioxabicyclo[14.1.0]heptadec-14-ene-10-acetaldehyde; antibiotic 67-694; juvenimicin A3; rosamicin
Manufacturers' Codes: M-4365A2; Sch-14947
Molecular Formula: C31H51NO9
Molecular Weight: 581.74
Percent Composition: C 64.00%, H 8.84%, N 2.41%, O 24.75%
Literature References: Macrolide antibiotic isolated from fermentations of Micromonospora rosaria NRRL-3718. Isoln and properties: M. J. Weinstein et al., ZA 7100402; FR 2081448 (1971, 1972 both to Sherico), C.A. 76, 139065n (1972); 78, 109310n (1973); G. H. Wagman et al., J. Antibiot. 25, 641 (1972). Biological studies: J. A. Waitz et al., ibid. 647. Structure: H. Reimann, R. S. Jaret, Chem. Commun. 1972, 1270. Crystal structure: A. K. Ganguly et al., Tetrahedron Lett. 21, 4699 (1980). Biosynthesis: A. K. Ganguly et al., J. Antibiot. 29, 976 (1976). Identity with juvenimicin A3: T. Kishi et al., ibid. 1171. Isoln from M. capillata MCRL 0940 and identity with antibiotic M-4365A2: A. Kinumaki et al., ibid. 30, 450 (1977). In vitro activity: S. Feltham et al., J. Antimicrob. Chemother. 5, 731 (1979). Use in experimental pneumococcal meningitis: C. M. Nolan et al., Antimicrob. Agents Chemother. 16, 776 (1979).
Properties: Crystals from chloroform, mp 119-122°. [a]D26 -35° (ethanol). uv max (methanol): 240 nm (e 14600). Very sol in methanol, acetone, chloroform, benzene. Sparingly sol in ether. Slightly sol in water. LD50 in mice (mg/kg): 625 s.c.; 350 i.p.; 155 i.v. (Wagman).
Melting point: mp 119-122°
Optical Rotation: [a]D26 -35° (ethanol)
Absorption maximum: uv max (methanol): 240 nm (e 14600)
Toxicity data: LD50 in mice (mg/kg): 625 s.c.; 350 i.p.; 155 i.v. (Wagman)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides.
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Rosaramicin
Rosamicin.svg
Identifiers
PubChem 6537204
ChemSpider 5020508
Jmol-3D images Image 1
Properties
Molecular formula C31H51NO9
Molar mass 581.74 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Rosaramicin (rosamicin) is an antibacterial substance chemically a lipid soluble basic macrolide similar to erythromycin but with a better activity against Gram-negative bacteria.

Experiments in dogs have shown that it is more concentrated in the prostate than erythromycin is, and thus may be better for treating infections of that organ. [1]