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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H36N2O11
Molecular Weight 612.6255
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOVOBIOCIN

SMILES

CC(=CCc1cc(ccc1O)C(=O)Nc2c(c3ccc(c(C)c3oc2=O)O[C@@]4([H])[C@@]([H])([C@@]([H])([C@]([H])(C(C)(C)O4)OC)OC(=N)O)O)O)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 612.6255
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.federalregister.gov/documents/2011/01/19/2011-1000/determination-that-albamycin-novobiocin-sodium-capsule-250-milligrams-was-withdrawn-from-sale-for | https://www.ncbi.nlm.nih.gov/pubmed/3036023

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other aminocoumarin antibiotics act as a potent competitive inhibitor of DNA gyrase B. The oral form of the drug was withdrawn from the market in 1999 due to safety or effectiveness reasons.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.

Originator

Curator's Comment:: Novobiocin is the generic name that has been adopted for two new antibiotics which were discovered independently of each other and later found to be identical. One of these, Cathomycin, a product of Upjohn Company, is derived by from Streptomyces spheroides n. sp., and the other, streptonivicin, is derived from Streptomyces niveus by Pfizer. # Pfizer, Upjohn Company

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL1795086
Target ID: Q5HK03
Gene ID: NA
Gene Symbol: gyrB
Target Organism: Staphylococcus epidermidis (strain ATCC 35984 / RP62A)
0.900000000000000022 µM [IC50]
300 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ALBAMYCIN

Approved Use

Treatment of serious infections due to susceptible strains of Staphylococcus aureus when other less toxic antibiotics such as the penicillins, cephalosporins, vancomycin, lincomycin, erythromycin, and the tetracyclines cannot be used.

Launch Date

-168048000000
Primary
Primary
Primary
Curative
ALBADRY PLUS

Approved Use

ALBADRY PLUS Suspension is indicated for the treatment, in dry cows only, of subclinical mastitis caused by susceptible strains of Staphylococcus aureus and Streptococcus agalactiae.

Launch Date

410745600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
62.5 μg/mL
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NOVOBIOCIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
407 μg × h/mL
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NOVOBIOCIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.85 h
500 mg 2 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
NOVOBIOCIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
unknown, unknown
NOVOBIOCIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 g 1 times / day steady, oral
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M
Sources:
Other AEs: Jaundice...
Other AEs:
Jaundice (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Jaundice 1 patient
2 g 1 times / day steady, oral
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Clinical effectiveness and safety of novobiocin.
1956 Apr
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
In vitro activity of DNA gyrase inhibitors, singly and in combination, against Mycobacterium avium complex.
1992 May-Jun
Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani.
2005 May
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
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

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: Other
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 Fri Jun 25 23:28:22 UTC 2021
Edited
by admin
on Fri Jun 25 23:28:22 UTC 2021
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 Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
CFR 21 CFR 526.1696D
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
CFR 21 CFR 526.1590
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
NCI_THESAURUS C258
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
CFR 21 CFR 558.415
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
CFR 21 CFR 556.460
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
Code System Code Type Description
PUBCHEM
54675769
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
MERCK INDEX
M8081
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY Merck Index
RXCUI
7538
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY RxNorm
EVMPD
SUB09385MIG
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-146-3
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
DRUG BANK
DB01051
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
HSDB
7443
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
MESH
D009675
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
FDA UNII
17EC19951N
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
EPA CompTox
303-81-1
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
DRUG CENTRAL
1974
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
USP_CATALOG
1475008
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
NOVOBIOCIN
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
INN
575
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL36506
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
NCI_THESAURUS
C705
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
CAS
303-81-1
Created by admin on Fri Jun 25 23:28:22 UTC 2021 , Edited by admin on Fri Jun 25 23:28:22 UTC 2021
PRIMARY
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