Novobiocin

Modify Date: 2025-08-23 19:20:53

Novobiocin Structure
Novobiocin structure
Common Name Novobiocin
CAS Number 303-81-1 Molecular Weight 612.624
Density 1.4±0.1 g/cm3 Boiling Point 848.2±65.0 °C at 760 mmHg
Molecular Formula C31H36N2O11 Melting Point 170-172°C (lit.)
MSDS Chinese Flash Point 466.8±34.3 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Novobiocin


Novobiocin (Albamycin) is a potent and orally active antibiotic. Novobiocin also is a DNA gyrase inhibitor and a heat shock protein 90 (Hsp90) antagonist. Novobiocin has the potential for the research of highly beta-lactam-resistant pneumococcal infections. Novobiocin shows anti-orthopoxvirus activity[1][2][3][4][6].

 Names

Name novobiocin
Synonym More Synonyms

 Novobiocin Biological Activity

Description Novobiocin (Albamycin) is a potent and orally active antibiotic. Novobiocin also is a DNA gyrase inhibitor and a heat shock protein 90 (Hsp90) antagonist. Novobiocin has the potential for the research of highly beta-lactam-resistant pneumococcal infections. Novobiocin shows anti-orthopoxvirus activity[1][2][3][4][6].
Related Catalog
Target

HSP90

In Vitro Novobiocin (1 mM) competitively inhibits ATP binding to gyrase B to interfere with nucleotide binding and interferes with the association of the co-chaperones Hsc70 and p23 with Hsp90[1]. Novobiocin (200 µM; 24 h) inhibits the rate of repair of both cis-DDP and BCNU induced DNA interstrand cross-links and with a corresponding decrease in the clonogenic survival of the human glioblastoma multiforme cells[2]. Novobiocin (0.3 mM; 48 hours) induces a caspase-3/7 enzyme–dependent apoptosis assays with an induction of approximately three- to fivefold of apoptotic cells in K562, HL60, Mutz-2[5].
In Vivo Novobiocin (25, 50, 100, 200 mg/kg; s.c.; 4 times at 1, 5, 24 and 48 h after infection) shows anti-infection activity in mice infected with amoxicillin-resistant Streptococcus pneumoniae[3]. Animal Model: 30 g adult female Swiss mice (sepsis induced by the penicillin-susceptible strain (AR33118))[3] Dosage: 25, 50, 100, 200 mg/kg Administration: S.c.; given at 1, 5, 24 and 48 h after infection Result: Showed anti-infection activity in mice infected with amoxicillin-resistant S. pneumoniae.
References

[1]. Marcu MG, et al. The heat shock protein 90 antagonist novobiocin interacts with a previously unrecognized ATP-binding domain in the carboxyl terminus of the chaperone. J Biol Chem. 2000 Nov 24;275(47):37181-6.

[2]. Ali-Osman F, et al. Topoisomerase II inhibition and altered kinetics of formation and repair of nitrosourea and cisplatin-induced DNA interstrand cross-links and cytotoxicity in human glioblastoma cells. Cancer Res. 1993 Dec 1;53(23):5663-8.

[3]. Rodríguez-Cerrato V, et al. Comparative efficacy of novobiocin and amoxicillin in experimental sepsis caused by beta-lactam-susceptible and highly resistant pneumococci. Int J Antimicrob Agents. 2010 Jun;35(6):544-9.

[4]. Eder JP, et al. A phase I clinical trial of novobiocin, a modulator of alkylating agent cytotoxicity. Cancer Res. 1991 Jan 15;51(2):510-3.

[5]. Bhatia S, et al. Targeting HSP90 dimerization via the C terminus is effective in imatinib-resistant CML and lacks the heat shock response.Blood. 2018 Jul 19;132(3):307-320.

[6]. Smee DF. Progress in the discovery of compounds inhibiting orthopoxviruses in animal models. Antivir Chem Chemother. 2008;19(3):115-24.

[7]. Smee DF. Progress in the discovery of compounds inhibiting orthopoxviruses in animal models. Antivir Chem Chemother. 2008;19(3):115-24.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 848.2±65.0 °C at 760 mmHg
Melting Point 170-172°C (lit.)
Molecular Formula C31H36N2O11
Molecular Weight 612.624
Flash Point 466.8±34.3 °C
Exact Mass 612.231934
PSA 200.01000
LogP 2.37
Vapour Pressure 0.0±3.3 mmHg at 25°C
Index of Refraction 1.640

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CU9080000
CHEMICAL NAME :
Benzamide, N-(7-((3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-met hyl-beta-L-lyxo- hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2H-1-benz opyran-3-yl)-4-hydrox y- 3-(3-methyl-2-butenyl)-
CAS REGISTRY NUMBER :
303-81-1
LAST UPDATED :
199410
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C31-H36-N2-O11
MOLECULAR WEIGHT :
612.69
WISWESSER LINE NOTATION :
T66 BOVJ DMVR DQ C2UY1&1& EQ J1 IO- FT6OTJ B1 B1 CV1 DOVZ EQ &-NA-

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human
DOSE/DURATION :
171 mg/kg/12D-C
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - conjunctive irritation Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
262 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
407 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
200 mg/L
REFERENCE :
CHROAU Chromosoma. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1939- Volume(issue)/page/year: 85,603,1982

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H317
Precautionary Statements P280-P301 + P312 + P330
Hazard Codes Xi
RIDADR NONH for all modes of transport

 Synonyms

Notonesomycin
(3R,4S,5R,6R)-5-Hydroxy-6-[(2-hydroxy-3-{[4-hydroxy-3-(3-methyl-2-buten-1-yl)benzoyl]amino}-8-methyl-4-oxo-4H-chromen-7-yl)oxy]-3-methoxy-2,2-dimethyltetrahydro-2H-pyran-4-yl carbamate (non-preferred name)
Novobiocin
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