Novobiocin

• Catalog No.: DB01051
• CAS Number: 303-81-1
• M. F.: C31H36N2O11
• M. W.: 612.62434

SYNONYMS

• IUPAC name: (3R,4S,5R,6R)-5-hydroxy-6-({4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-8-methyl-2-oxo-2H-chromen-7-yl}oxy)-3-methoxy-2,2-dimethyloxan-4-yl carbamate
• IUPAC Traditional name: (3R,4S,5R,6R)-5-hydroxy-6-({4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-8-methyl-2-oxochromen-7-yl}oxy)-3-methoxy-2,2-dimethyloxan-4-yl carbamate
• Brand Name: Albamycin; Cathomycin; Inamycin; Spheromycin; Albamix; Cardelmycin; Cathocin; Novo-R; Robiocina; Sirbiocina; Stilbiocina; Streptonivicin
• Synonyms: Novobiocine [INN-French]; Novobiocina [INN-Spanish]; Crystallinic Acid; Antibiotic Pa-93; Novobiocinum [INN-Latin]; NOV

DATABASE IDS

• PubChem CID: 9346
• CAS Number: 303-81-1
• PubChem SID: 46507250

PROPERTIES

• Hydrophobicity(logP): 4.1
• Solubility: Insoluble

DETAILS

Description (English)

• Drug Groups: approved
• Description: 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) [PubChem]
• Indication: For the treatment of infections due to staphylococci and other susceptible organisms
• Pharmacology: Novobiocin is an aminocoumarin antibiotic that was produced by the actinomycete Streptomyces niveus. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. Other antibiotics in the aminocoumarin class include coumermycin A1 and clorobiocin.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Oral bioavailability is negligible.
• Half Life: 6 hours
• Protein Binding: 95%
• References: Vickers AA, Chopra I, O'neill AJ: Intrinsic novobiocin resistance in Staphylococcus saprophyticus. Antimicrob Agents Chemother. 2007 Sep 17;. [Pubmed] ; Burlison JA, Neckers L, Smith AB, Maxwell A, Blagg BS: Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90. J Am Chem Soc. 2006 Dec 6;128(48):15529-36. [Pubmed] ; Singh G, Jayanarayan KG, Dey CS: Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. Mol Biochem Parasitol. 2005 May;141(1):57-69. [Pubmed] ; CORBIN EE, PRIGOT A: Novobiocin; absorption, diffusion, and excretion studies. Antibiot Annu. 1956-1957;:392-5. [Pubmed] ; DAVID NA, BURGNER PR: Clinical effectiveness and safety of novobiocin. Antibiotic Med Clin Ther. 1956 Apr;2(4):219-29. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Vickers AA, Chopra I, O'neill AJ: Intrinsic novobiocin resistance in Staphylococcus saprophyticus. Antimicrob Agents Chemother. 2007 Sep 17;. Pubmed
• Burlison JA, Neckers L, Smith AB, Maxwell A, Blagg BS: Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90. J Am Chem Soc. 2006 Dec 6;128(48):15529-36. Pubmed
• Singh G, Jayanarayan KG, Dey CS: Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. Mol Biochem Parasitol. 2005 May;141(1):57-69. Pubmed
• CORBIN EE, PRIGOT A: Novobiocin; absorption, diffusion, and excretion studies. Antibiot Annu. 1956-1957;:392-5. Pubmed
• DAVID NA, BURGNER PR: Clinical effectiveness and safety of novobiocin. Antibiotic Med Clin Ther. 1956 Apr;2(4):219-29. Pubmed