NOVOBIOCIN SODIUM SALT Chemical Properties

Melting point:

215-220 C

alpha 

D24 -38° (c = 2.5 in 95% ethanol); D24 -33° (c = 2.5 in water)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

H2O: soluble50mg/mL

form 

White to yellow solid

color 

white to faintly beige

PH

7.5 (100g/l, H2O, 25℃)

optical activity

[α]20/D 48±3°, c = 1% in ethanol

Water Solubility 

Soluble in water at 100mg/ml. Also soluble in ethanol or DMSOSoluble in water, ethanol, dimethyldulfoxide and methanol.

Merck 

13,6755

BRN 

3892910

Stability:

Hygroscopic

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

43-36-36/37/38-20/21/22

Safety Statements 

36-36/37-26-37/39

WGK Germany 

2

RTECS 

RD5425000

F 

8-10

HS Code 

2941 90 00

Toxicity

LD50 orally in Rabbit: 3500 mg/kg

MSDS

• Language:English Provider:SigmaAldrich

NOVOBIOCIN SODIUM SALT Usage And Synthesis

Chemical Properties

crystalline

Uses

Topoisomerase II inhibitorNovobiocin sodium salt is effective an antistaphylococcal agent used in the treatment of Methicillin-resistant Staphylococcus aureus (MRSA). It is also used to inhibit the activity of retroviral RNA-dependent DNA polymerase as well as inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase.

Uses

Novobiocin is an antibiotic that acts as an inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase. Studies show that Novobiocin is also an inhibitor of retrovirus RNA-dependent DNA-polymerase. Novobiocin is used in the production of positively supercoiled plasmid DNA.
Novobiocin sodium salt is twice as bioavailable as the calcium salt and 50 times more available than the parent acid.

Uses

antibacterial

brand name

Albamycin (Pharmacia & Upjohn).

Clinical Use

The action of novobiocin is largely bacteriostatic. Itsmode of action is not known with certainty, though it doesinhibit bacterial protein and nucleic acid synthesis. Studiesindicate that novobiocin and related coumarin-containingantibiotics bind to the subunit of DNA gyrase and possiblyinterfere with DNA supercoiling and energy transductionin bacteria. The effectiveness of novobiocin is confinedlargely to Gram-positive bacteria and a few strains of P. vulgaris.Its low activity against Gram-negative bacteria is apparentlybecause of poor cellular penetration.
Although cross-resistance to other antibiotics is reportednot to develop with novobiocin, resistant S. aureus strainsare known. Consequently, the medical use of novobiocin isreserved for the treatment of staphylococcal infections resistantto other antibiotics and sulfas and for patients allergicto these drugs. Another shortcoming that limits the usefulnessof novobiocin is the relatively high frequency ofadverse reactions, such as urticaria, allergic rashes, hepatotoxicity,and blood dyscrasias.

Safety Profile

Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. Mutation data reported. An antibiotic with serious side effects which include liver and blood disease. It may also promote the development of resistant strains of staphylococcus. When heated to decomposition it emits toxic fumes of NOx and Na2O.

Purification Methods

The sodium salt has been recrystallised from MeOH, then dried at 60o/0.5mm. [Sensi et al, Anal Chem 29 1611 1957, Kaczka et al. J Am Chem Soc 78 4126 1956, Beilstein 18/8 IV 8125.]

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