| Stereochemistry | ABSOLUTE |
| Molecular Formula | C31H36N2O11 |
| Molecular Weight | 612.6243 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](OC2=CC=C3C(O)=C(NC(=O)C4=CC(CC=C(C)C)=C(O)C=C4)C(=O)OC3=C2C)OC1(C)C
InChI
InChIKey=YJQPYGGHQPGBLI-KGSXXDOSSA-N
InChI=1S/C31H36N2O11/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1
| Molecular Formula | C31H36N2O11 |
| Molecular Weight | 612.6243 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Novobiocin (also known as streptonivicin) is an aminocoumarin antibiotic, active against Staphylococcus epidermidis. Novobiocin and other aminocoumarin antibiotics act as a potent competitive inhibitor of DNA gyrase B. The oral form of the drug was withdrawn from the market in 1999 due to safety or effectiveness reasons. Later it was discovered that novobiocin inhibited Hsp90 and topoisomerase II, and novobiocin was investigated in clinical trials against metastatic breast cancer and non-small cell lung cancer. Topical form of novobiocin was investigated in combination with nalidixic acid for treatment of psoriasis.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
Sourcing
Sample Use Guides
As antibiotic, novobiocin was marketed in 250 mg capsules and administered orally. For the treatment of psoriasis, novobiocin (2% or 5%) in methylcellulose were applied twice daily under occlusion.
Route of Administration:
Other
Minimal inhibitory concentration of novobiocin against a panel of microorganisms were determined by using the broth microdilution procedure recommended by the National Committee for Clinical Laboratory Standards.Microtiter plates (96 wells/plate; final assay volume, 100 μl per well) were inoculated with exponential-phase cells and incubated overnight at 35°C in ambient air. Wells were examined for bacterial growth by using an illuminated microtiter plate reader fitted with a magnifying mirror. MIC for Staphylococcus aureus was <= 0.06 ug/ml.
