U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C31H36N2O11
Molecular Weight 612.6243
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOVOBIOCIN

SMILES

CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](OC2=C(C)C3=C(C=C2)C(O)=C(NC(=O)C4=CC=C(O)C(CC=C(C)C)=C4)C(=O)O3)OC1(C)C

InChI

InChIKey=YJQPYGGHQPGBLI-KGSXXDOSSA-N
InChI=1S/C31H36N2O11/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)/t23-,25+,26-,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula C31H36N2O11
Molecular Weight 612.6243
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Novobiocin (also known as streptonivicin) is an aminocoumarin antibiotic, active against Staphylococcus epidermidis. Novobiocin and other aminocoumarin antibiotics act as a potent competitive inhibitor of DNA gyrase B. The oral form of the drug was withdrawn from the market in 1999 due to safety or effectiveness reasons. Later it was discovered that novobiocin inhibited Hsp90 and topoisomerase II, and novobiocin was investigated in clinical trials against metastatic breast cancer and non-small cell lung cancer. Topical form of novobiocin was investigated in combination with nalidixic acid for treatment of psoriasis.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Clinical effectiveness and safety of novobiocin.
1956 Apr
Novobiocin; absorption, diffusion, and excretion studies.
1956-1957
Novobiocin: activity in vitro and in experimental tuberculosis.
1957 Aug
Screening for new compounds with antiherpes activity.
1984 Oct
Antiviral activity and inhibition of topoisomerase by ofloxacin, a new quinolone derivative.
1987 Oct
Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs.
1988 Feb
Novobiocin-induced anti-proliferative and differentiating effects in melanoma B16.
1992 Feb
In vitro activity of DNA gyrase inhibitors, singly and in combination, against Mycobacterium avium complex.
1992 May-Jun
Novobiocin is a novel inducer of CD38 on cells of the myelomonocytic lineage.
2002 Jan 30
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.
2005 May
Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani.
2005 May
Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90.
2006 Dec 6
Discrepancy between the occurrence of Arcobacter in chickens and broiler carcass contamination.
2007 Apr
Characterization of the Arcobacter contamination on Belgian pork carcasses and raw retail pork.
2007 Aug 15
Intrinsic novobiocin resistance in Staphylococcus saprophyticus.
2007 Dec
Combinatorial biosynthesis, metabolic engineering and mutasynthesis for the generation of new aminocoumarin antibiotics.
2008
Drug-sensing hydrogels for the inducible release of biopharmaceuticals.
2008 Oct
Responsive hydrogels for label-free signal transduction within biosensors.
2010
Antibiotic Resistance in Staphylococcus aureus and Coagulase Negative Staphylococci Isolated from Goats with Subclinical Mastitis.
2010
Detection of Escherichia coli O157 and Escherichia coli O157:H7 by the immunomagnetic separation technique and stx1 and stx2 genes by multiplex PCR in slaughtered cattle in Samsun Province, Turkey.
2010 Dec
Biliary efflux transporters involved in the clearance of rosuvastatin in sandwich culture of primary rat hepatocytes.
2010 Mar
Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen.
2011 Aug
Aminopyrazinamides: novel and specific GyrB inhibitors that kill replicating and nonreplicating Mycobacterium tuberculosis.
2013 Mar 15
Patents

Sample Use Guides

In Vivo Use Guide
As antibiotic, novobiocin was marketed in 250 mg capsules and administered orally. For the treatment of psoriasis, novobiocin (2% or 5%) in methylcellulose were applied twice daily under occlusion.
Route of Administration: oral; topical
In Vitro Use Guide
Minimal inhibitory concentration of novobiocin against a panel of microorganisms were determined by using the broth microdilution procedure recommended by the National Committee for Clinical Laboratory Standards.Microtiter plates (96 wells/plate; final assay volume, 100 μl per well) were inoculated with exponential-phase cells and incubated overnight at 35°C in ambient air. Wells were examined for bacterial growth by using an illuminated microtiter plate reader fitted with a magnifying mirror. MIC for Staphylococcus aureus was <= 0.06 ug/ml.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:47:59 UTC 2019
Edited
by admin
on Mon Oct 21 19:47:59 UTC 2019
Record UNII
17EC19951N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NOVOBIOCIN
GREEN BOOK   HSDB   INN   MART.   MI   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
BENZAMIDE, N-(7-((3-O-(AMINOCARBONYL)-6-DEOXY-5-C-METHYL-4-O-METHYL-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-4-HYDROXY-8-METHYL-2-OXO-2H-1-BENZOPYRAN-3-YL)-4-HYDROXY-3-(3-METHYL-2-BUTEN-1-YL)-
Common Name English
NOVOBIOCIN [GREEN BOOK]
Common Name English
NOVOBIOCIN [HSDB]
Common Name English
NOVOBIOCIN [WHO-DD]
Common Name English
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)-
Common Name English
NOVOBIOCIN [MI]
Common Name English
NOVOBIOCIN [USP-RS]
Common Name English
NOVOBIOCIN [INN]
Common Name English
NOVOBIOCIN [VANDF]
Common Name English
NOVOBIOCIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01XX95
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
CFR 21 CFR 526.1696D
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
CFR 21 CFR 526.1590
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
NCI_THESAURUS C258
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
CFR 21 CFR 558.415
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
CFR 21 CFR 556.460
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
Code System Code Type Description
PUBCHEM
54675769
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
MERCK INDEX
M8081
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY Merck Index
RXCUI
7538
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY RxNorm
EVMPD
SUB09385MIG
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
ECHA (EC/EINECS)
206-146-3
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
DRUG BANK
DB01051
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
HSDB
303-81-1
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
MESH
D009675
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
EPA CompTox
303-81-1
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
WIKIPEDIA
NOVOBIOCIN
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
INN
575
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
ChEMBL
CHEMBL36506
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
NCI_THESAURUS
C705
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
CAS
303-81-1
Created by admin on Mon Oct 21 19:47:59 UTC 2019 , Edited by admin on Mon Oct 21 19:47:59 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY