| Stereochemistry | ABSOLUTE |
| Molecular Formula | C55H59N5O20 |
| Molecular Weight | 1110.0785 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@@H]1[C@@H](OC(=O)C2=CC=C(C)N2)[C@@H](O)[C@H](OC3=C(C)C4=C(C=C3)C(O)=C(NC(=O)C5=CNC(C(=O)NC6=C(O)C7=C(OC6=O)C(C)=C(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)C9=CC=C(C)N9)[C@H]8O)C=C7)=C5C)C(=O)O4)OC1(C)C
InChI
InChIKey=WTIJXIZOODAMJT-DHFGXMAYSA-N
InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1
Coumermycin is from the aminocoumarin class of antibiotic compounds which acts by inhibiting DNA gyrase. Coumermycin is effective against gram-positive bacteria, but not gram-negative bacteria. Coumermycin its derivatives have been studied since the 1950's as potential antibiotic. However, it has seen little to no clinical development because of its low water solubility, toxicity profile, and ineffectiveness against gram-negative bacteria.
Originator
Approval Year
PubMed
Sample Use Guides
Lethal septicemia was induced in mice by intraperitoneal administration of Methicillin-Resistant Staphylococcus. The infection was successfully treated in 50% of the animals (ED50) following a dose of 0.9 micro-g/g body weight. This was significantly better than ofloxacin and vancomycin.
Route of Administration:
Other
The antibiotic ability of coumermycin was evaluated against 232 bacterial strains. Minimal inhibitory concentrations (MIC) were determined in trypticase soy broth using twofold serial dilutions. The last tube in a series to show no visible growth after 18 hours at 37 deg-C was considered the MIC. Strain specific MIC's were reported between 0.002 micro-g/L and 100 micro-g/L.
ACTIVE MOIETY
