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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C31H35N2O11.Ca
Molecular Weight 1263.3132
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOVOBIOCIN CALCIUM

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.CC(=CCc1cc(ccc1[O-])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.[Ca+2]

InChI

InChIKey=HEJBMFPJLCJWER-CWPVBXIBSA-L
InChI=1S/2C31H36N2O11.Ca/c2*1-14(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;/h2*7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q;;+2/p-2/t2*23-,25+,26-,29-;/m11./s1

HIDE SMILES / InChI

Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C31H35N2O11
Molecular Weight 611.6176
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including 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withdrawn-from-sale-for | https://www.ncbi.nlm.nih.gov/pubmed/3036023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other aminocoumarin antibiotics act as a potent competitive inhibitor of DNA gyrase B. The oral form of the drug was withdrawn from the market in 1999 due to safety or effectiveness reasons.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)
0.9 µM [IC50]
300.0 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

-1.68048001E11
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
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

4.10745602E11
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; 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
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
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
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
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 Sat Jun 26 12:05:46 UTC 2021
Edited
by admin
on Sat Jun 26 12:05:46 UTC 2021
Record UNII
RHW5BU180N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NOVOBIOCIN CALCIUM
MART.   WHO-DD  
Common 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-BUTENYL)-, CALCIUM SALT (2:1)
Common Name English
NOVOBIOCIN CALCIUM [WHO-DD]
Common Name English
CALCIUM NOVOBIOCIN
Common Name English
NOVOBIOCIN, CALCIUM SALT
Common Name English
NOVOBIOCIN CALCIUM [MART.]
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)-, CALCIUM SALT (2:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C258
Created by admin on Sat Jun 26 12:05:46 UTC 2021 , Edited by admin on Sat Jun 26 12:05:46 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
224-321-2
Created by admin on Sat Jun 26 12:05:46 UTC 2021 , Edited by admin on Sat Jun 26 12:05:46 UTC 2021
PRIMARY
CAS
4309-70-0
Created by admin on Sat Jun 26 12:05:46 UTC 2021 , Edited by admin on Sat Jun 26 12:05:46 UTC 2021
PRIMARY
FDA UNII
RHW5BU180N
Created by admin on Sat Jun 26 12:05:46 UTC 2021 , Edited by admin on Sat Jun 26 12:05:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL36506
Created by admin on Sat Jun 26 12:05:46 UTC 2021 , Edited by admin on Sat Jun 26 12:05:46 UTC 2021
PRIMARY
PUBCHEM
76963834
Created by admin on Sat Jun 26 12:05:46 UTC 2021 , Edited by admin on Sat Jun 26 12:05:46 UTC 2021
PRIMARY
NCI_THESAURUS
C81448
Created by admin on Sat Jun 26 12:05:46 UTC 2021 , Edited by admin on Sat Jun 26 12:05:46 UTC 2021
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY