| Identification | Back Directory | [Name]
NOVOBIOCIN SODIUM SALT | [CAS]
1476-53-5 | [Synonyms]
U-6591
Albadry
NSC 2382
Robicina
ALBAMYCIN
Vulcamycin
Albycin sodium
MSRV Selective
STREPTONIVICIN
Albamycinsodium
Sodiumalbamycin
Sodiumnovobiocin
Cathomycinsodium
NOVOBIOCIN SODIUM
NOVOBIOCIN NA-SALT
albamycin(capsule)
Monosodiumnovobiocin
Novobiocinmonosodium
Novobiocin sodium saL
novobiocin sodium usp
Cathomycinsodiumlyovac
NOVOBIOCIN SODIUM SALT
Novobiocin,sodiumderiv.
Novobiocin Sodium, >98%
MSRV SELECTIVE SUPPLEMENT
NOVOBIOCIN MONOSODIUM SALT
Novobiocin Sodium (U-6591)
Novobiocin sodiuM(AlbaMycin)
novobiocin sodium crystalline
Novobiocin Sodium Salt Standard
NOVOBIOCIN SODIUM SALT USP/EP/BP
NOVOBIOCIN SODIUM SALT APPOX. 90%
Novobiocin-Na-salt research grade
Crystallinic acid MonosodiuM salt
Antibiotic from streptomyces spheroides
NOVOBIOCIN SODIUM SALT VETRANAL, 250
NOVOBIOCINE MONOSODIUM FPC(CRM STANDARD)
Novobiocin, Sodium Salt - CAS 1476-53-5 - Calbiochem
Novobiocin sodium salt, Antibiotic for Culture Media Use Only
4-Hydroxy-3-[4-hydroxy-3-(3-methylbut-2-enyl) benzamido]-8-methylcoumarin-7-yl 3-O-carbamoyl-5,5-di-C-methyl-α-L-lyxofuranoside sodium salt
7-[4-(Carbamoyloxy)-tetrahydro-3-hydroxy-5-methoxy-6,6-dimethylpyran-2-yl]-4-hydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)benzamido]-8-methyl-, sodium salt
N-[7-[(3-O-Carbamoyl-4-O,5-C-dimethyl-6-deoxy-β-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-sodiooxy-3-(3-methyl-2-butenyl)benzamide
N-[7-[[3-O-(AMinocarbonyl)-6-deoxy-5-C-Methyl-4-O-Methyl-α-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-Methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-Methyl-2-butenyl)benzaMide MonosodiuM salt
Benzamide, N-7-3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-.alpha.-L-lyxo-hexopyranosyloxy-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl-4-hydroxy-3-(3-methyl-2-butenyl)-, monosodium salt
Sodium 4-((7-(((2R,3R,4S,5R)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-8-methyl-2-oxo-2H-chromen-3-yl)carbamoyl)-2-(3-methylbut-2-en-1-yl)phenolate
Benzamide,N-[7-[[3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-a-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-methyl-2-buten-1-yl)-,sodium salt (1:1)
N-[7-[[3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-methyl-2-buten-1-yl)-benzamide, sodium salt (1:1)
Benzamide, N-[7-[[3-o-(aminocarbonyl)-6-deoxy-5-C-methyl-4-o-methyl-.beta.-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl]-4-hydroxy-3-(3-methyl-2-butenyl)-, monosodium salt | [EINECS(EC#)]
216-023-6 | [Molecular Formula]
C31H35N2NaO11 | [MDL Number]
MFCD00066541 | [MOL File]
1476-53-5.mol | [Molecular Weight]
634.61 |
| Chemical Properties | Back Directory | [Melting point ]
215-220 C | [alpha ]
D24 -38° (c = 2.5 in 95% ethanol); D24 -33° (c = 2.5 in water) | [storage temp. ]
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 |
| Hazard Information | Back Directory | [Chemical Properties]
crystalline | [Uses]
antibacterial | [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.
| [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. | [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.] |
| Safety Data | Back Directory | [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 ]
29419090 | [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. | [Toxicity]
LD50 orally in Rabbit: 3500 mg/kg |
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