Rosaramicin

Rosaramicin

Names
IUPAC name (1S,2R,3R,7R,8S,9S,10R,12R,14E,16S)-3-Ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl 3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranoside
Other names Rosamicin; Juvenimicin A3
Identifiers
ChEBI	CHEBI:87084
ChEMBL	ChEMBL8965
ChemSpider	5020508
Jmol interactive 3D	Image
PubChem	6537204
InChI InChI=1S/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1 Key: IUPCWCLVECYZRV-JZMZINANSA-N InChI=1/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1 Key: IUPCWCLVECYZRV-JZMZINANBR
SMILES O=CC[C@@H]2[C@H](O[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C)[C@@H](C)[C@H](O)CC(=O)O[C@H](CC)[C@@H](C)[C@@H]3O[C@]3(\C=C\C(=O)[C@H](C)C2)C
Properties
Chemical formula	C31H51NO9
Molar mass	581.75 g·mol^−1
Except where otherwise noted, 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]

References

1. Baumueller A, Kjaer TB, Madsen PO (September 1977). "Prostatic tissue and secretion concentrations of rosamicin and erythromycin. Experimental studies in the dog". Invest Urol 15 (2): 158–60. PMID 903212.