Rosaramicin

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

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-9-[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyloxy]-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl}acetaldehyde
Preferred IUPAC name
[(1S,2R,3R,7R,8S,9S,10R,12R,14E,16S)-9-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde
Other names
Rosamicin; Juvenimicin A3
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.047.933
EC Number
  • 252-742-1
KEGG
PubChem CID
UNII
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 581.747 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

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.


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