Novobiocin sodiumProduct ingredient for Novobiocin
- Name
- Novobiocin sodium
- Drug Entry
- Novobiocin
Novobiocin is an antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189)
Novobiocin sodium, a salt form of novobiocin, was initially approved in September 1964 and was indicated for the treatment of serious infections due to susceptible strains of Staphylococcus aureus when other less toxic antibiotics cannot be used. In 2009, the FDA determined novobiocin sodium was withdrawn from sale for reasons of safety or effectiveness.6,7
- Accession Number
- DBSALT001020
- Structure
Structure for Novobiocin sodium (DBSALT001020)
- Synonyms
- Not Available
- UNII
- Q9S9NQ5YIY
- CAS Number
- 1476-53-5
- Weight
- Average: 634.614
Monoisotopic: 634.21385424 - Chemical Formula
- C31H35N2NaO11
- InChI Key
- WWPRGAYLRGSOSU-RNROJPEYSA-M
- InChI
- InChI=1S/C31H36N2O11.Na/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);/q;+1/p-1/t23-,25+,26-,29-;/m1./s1
- IUPAC Name
- sodium 4-[(4-hydroxy-7-{[(2R,3R,4S,5R)-3-hydroxy-4-(C-hydroxycarbonimidoyloxy)-5-methoxy-6,6-dimethyloxan-2-yl]oxy}-8-methyl-2-oxo-2H-chromen-3-yl)carbamoyl]-2-(3-methylbut-2-en-1-yl)benzen-1-olate
- SMILES
- [Na+].[H][C@]1(O)[C@]([H])(OC2=C(C)C3=C(C=C2)C(O)=C(NC(=O)C2=CC=C([O-])C(CC=C(C)C)=C2)C(=O)O3)OC(C)(C)[C@]([H])(OC)[C@@]1([H])OC(O)=N
- External Links
- KEGG Compound
- C12609
- ChemSpider
- 17215268
- ChEBI
- 31924
- ChEMBL
- CHEMBL3183453
- Wikipedia
- Novobiocin
- Predicted Properties
Property Value Source Water Solubility 0.0188 mg/mL ALOGPS logP 3.48 ALOGPS logP 1.41 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) -3.3 Chemaxon pKa (Strongest Basic) 11.11 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 199.92 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 180 m3·mol-1 Chemaxon Polarizability 64.17 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon