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303-81-1

Basic Information
CAS No.: 303-81-1
Name: Novobiocin
Article Data: 9
Molecular Structure:
Molecular Structure of 303-81-1 (Novobiocin)
Formula: C31H36 N2 O11
Molecular Weight: 612.634
Synonyms: 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-butenyl)-(9CI); Coumarin, 7-[4-(carbamoyloxy)tetrahydro-3-hydroxy-5-methoxy-6,6-dimethylpyran-2-yloxy]-4-hydroxy-3-[4-hydroxy-3-(3-methyl-2-butenyl)benzamido]-8-methyl-(6CI); Novobiocin (8CI); Albamix; Albamycin; Antibiotic PA-93; Cardelmycin;Cathocin; Cathomycin; Crystallinic acid; Inamycin; Novo-R; PA 93; Robiocina; Sirbiocina;Spheromycin; Stilbiocina; Streptonivicin; U 6391
Density: 1.42g/cm3
Melting Point: 170-172 °C
Boiling Point: 848.2°Cat760mmHg
Flash Point: 466.8°C
Hazard Symbols: May have damaging side effects.
Safety: Poison by intraperitoneal route. Moderately toxic by ingestion and intravenous routes. Human systemic effects by unspecified route: conjunctiva irritation and skin dermatitis. Human mutation data reported. An antibiotic with serious side effects which include liver and blood disease. It may also cause the development of resistant strains of staphylococcus. Used as a food additive permitted in the feed and drinking water of animals and/or for the treatment of food-producing animals; also permitted in food for human consumption. When heated to decomposition it emits toxic fumes of NOx.
PSA: 200.01000
LogP: 4.40040
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Chemistry

Formula: C31H36N2O11 
Mol. mass: 612.624

Uses

STREPTONIVICIN (303-81-1) may be used to differentiate from the other coagulase-negative Staphylococcus saprophyticus, which is resistant to novobiocin, in culture.
STREPTONIVICIN (303-81-1) is effective antistaphylococcal agent used in the treatment of MRSA.

Production

The 3-dimethylallyl-4-hydroxybenzoic acid moiety, known as ring A, is derived from prephenate and dimethylallyl pyrophosphate. The aminocoumarin moiety, known as ring B, is derived from L-Tyrosine. The final component of STREPTONIVICIN (303-81-1) is the sugar derivative L-noviose, known as ring C, which is derived from glucose-1-phosphate. Rings A, B, and C are coupled together and modified to give the finished STREPTONIVICIN (303-81-1) molecule.

Toxicity Data With Reference

1.   

mmo-esc 200 mg/L

   NATUAS    Nature. 271 (1978),385.
2.   

pic-esc 10 µg/plate

   CNREA8    Cancer Research. 43 (1983),2819.
3.   

dni-hmn:emb 600 mmol/L

   CRNGDP    Carcinogenesis. 3 (1982),1171.
4.   

cyt-mus-par 50 mg/kg

   NULSAK    Nucleus (Calcutta). 2 (1971),161.
5.   

dnr-ham:oth 200 mg/L

   CRNGDP    Carcinogenesis. 5 (1984),187.
6.   

unr-hmn TDLo:171 mg/kg/12D-C:EYE,SKN

   85ERAY    Antibiotics: Origin, Nature, and Properties. 1 (1978),137.
7.   

orl-mus LD50:1500 mg/kg

   85GDA2    CRC Handbook of Antibiotic Compounds, Volumes 1-9. 6 (1981),338.
8.   

ipr-mus LD50:262 mg/kg

   85FZAT    Index of Antibiotics from Actinomycetes Umezawa, H., et al., eds.,Tokyo, Japan.: University of Tokyo Press,1967,471.
9.   

ivn-mus LD50:407 mg/kg

   85FZAT    Index of Antibiotics from Actinomycetes Umezawa, H., et al., eds.,Tokyo, Japan.: University of Tokyo Press,1967,471.

Safety Profile

STREPTONIVICIN (303-81-1)  is poison by intraperitoneal route. Moderately toxic by ingestion and intravenous routes. Human systemic effects by unspecified route: conjunctiva irritation and skin dermatitis. Human mutation data reported. An antibiotic with serious side effects which include liver and blood disease. STREPTONIVICIN (303-81-1) may also cause the development of resistant strains of staphylococcus. Used as a food additive permitted in the feed and drinking water of animals and/or for the treatment of food-producing animals; also permitted in food for human consumption. When heated to decomposition it emits toxic fumes of NOx.