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Merck

N6160

Novobiocin sodium

meets USP testing specifications

Synonym(s):

Novobiocin sodium salt

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About This Item

Empirical Formula (Hill Notation):
C31H35N2NaO11
CAS Number:
1476-53-5
Molecular Weight:
634.61
NACRES:
NA.76
PubChem Substance ID:
24897774
UNSPSC Code:
51286504
EC Number:
216-023-6
Beilstein/REAXYS Number:
3892910

Key Documents

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InChI key

AXOUUAINTJNFRS-UHFFFAOYSA-N

InChI

1S/C31H35N2O11.Na/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h7,9-13,23,25-26,29,34,36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q-1;+1

SMILES string

[Na+].CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](Oc2ccc3C([O-])=C(NC(=O)c4ccc(O)c(C\C=C(\C)C)c4)C(=O)Oc3c2C)OC1(C)C

agency

USP/NF, meets USP testing specifications

form

powder

antibiotic activity spectrum

Gram-positive bacteria

application(s)

pharmaceutical (small molecule)

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

2-8°C

Quality Level

200

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Related Categories

Biochem/physiol Actions

Mode of Action: Inhibits DNA synthesis by inhibiting the enzyme Topoisomerase II.
Antimicrobial spectrum: Gram-positive bacterial.

General description

Chemical structure: coumarin-glycoside

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place

Application

For the production of positively supercoiled plasmid DNA. Inhibitor of bacterial DNA gyrase and eukaryotic DNA topoisomerase. Inhibitor of retrovirus RNA-dependent DNA-polymerase.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCL4333
SLCG1412
SLCF0910
SLBZ1048
SLBV9706

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Jeffery D Eskew et al.
BMC cancer, 11, 468-468 (2011-11-02)
The molecular chaperone, heat shock protein 90 (Hsp90) has been shown to be overexpressed in a number of cancers, including prostate cancer, making it an important target for drug discovery. Unfortunately, results with N-terminal inhibitors from initial clinical trials have
Huiping Zhao et al.
Bioorganic & medicinal chemistry letters, 23(2), 552-557 (2012-12-14)
Hsp90 is a promising therapeutic target for the treatment of cancer. Novobiocin is the first Hsp90 C-terminal inhibitor ever identified and recent structure-activity relationship studies on the noviose sugar identified several commercially available amines as suitable surrogates. In an effort
Bhaskar Reddy Kusuma et al.
Bioorganic & medicinal chemistry letters, 21(23), 7170-7174 (2011-10-22)
Novobiocin analogs lacking labile glycosidic ether have been designed, synthesized and evaluated for Hsp90 inhibitory activity. Replacement of the synthetically complex noviose sugar with simple aromatic side chains produced analogs that maintain moderate cytotoxic activity against MCF7 and SkBR3 breast
Sidharth Chopra et al.
The Journal of antimicrobial chemotherapy, 67(2), 415-421 (2011-11-05)
New classes of drugs are needed to treat tuberculosis (TB) in order to combat the emergence of resistance to existing agents and shorten the duration of therapy. Targeting DNA gyrase is a clinically validated therapeutic approach using fluoroquinolone antibiotics to
Roman Pantůček et al.
Systematic and applied microbiology, 36(2), 90-95 (2013-01-16)
Thirteen coagulase-negative, oxidase-negative, and novobiocin-susceptible staphylococci were isolated from human clinical specimens. The isolates were differentiated from known staphylococcal species on the basis of 16S rRNA, hsp60, rpoB, dnaJ, tuf, and gap gene sequencing, automated ribotyping, (GTG)5-PCR fingerprinting, and MALDI-TOF
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