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
SMILES
CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](OC2=CC=C3C(O)=C(NC(=O)C4=CC(CC=C(C)C)=C(O)C=C4)C(=O)OC3=C2C)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
DescriptionSources: https://www.drugbank.ca/drugs/DB01051Curator'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withdrawn-from-sale-for | https://www.ncbi.nlm.nih.gov/pubmed/3036023
Sources: https://www.drugbank.ca/drugs/DB01051
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withdrawn-from-sale-for | https://www.ncbi.nlm.nih.gov/pubmed/3036023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other aminocoumarin antibiotics act as a potent competitive inhibitor of DNA gyrase B. The oral form of the drug was withdrawn from the market in 1999 due to safety or effectiveness reasons.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.
CNS Activity
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1795086 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10945979 |
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Target ID: Q5HK03 Gene ID: NA Gene Symbol: gyrB Target Organism: Staphylococcus epidermidis (strain ATCC 35984 / RP62A) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16569821 |
0.9 µM [IC50] | ||
Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6098161 |
300.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ALBAMYCIN Approved UseTreatment 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 Date1964 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Curative | ALBADRY PLUS Approved UseALBADRY 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 Date1983 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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62.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3752982 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
407 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3752982 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3752982 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8243034 |
unknown, unknown |
NOVOBIOCIN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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 |
Other AEs: Jaundice... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
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Clinical effectiveness and safety of novobiocin. | 1956 Apr |
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Novobiocin; absorption, diffusion, and excretion studies. | 1956-1957 |
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Novobiocin: activity in vitro and in experimental tuberculosis. | 1957 Aug |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Antiviral activity and inhibition of topoisomerase by ofloxacin, a new quinolone derivative. | 1987 Oct |
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Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs. | 1988 Feb |
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Novobiocin-induced anti-proliferative and differentiating effects in melanoma B16. | 1992 Feb |
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In vitro activity of DNA gyrase inhibitors, singly and in combination, against Mycobacterium avium complex. | 1992 May-Jun |
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Novobiocin is a novel inducer of CD38 on cells of the myelomonocytic lineage. | 2002 Jan 30 |
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Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo. | 2005 May |
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Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. | 2005 May |
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Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90. | 2006 Dec 6 |
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Discrepancy between the occurrence of Arcobacter in chickens and broiler carcass contamination. | 2007 Apr |
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Characterization of the Arcobacter contamination on Belgian pork carcasses and raw retail pork. | 2007 Aug 15 |
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Intrinsic novobiocin resistance in Staphylococcus saprophyticus. | 2007 Dec |
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Combinatorial biosynthesis, metabolic engineering and mutasynthesis for the generation of new aminocoumarin antibiotics. | 2008 |
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Drug-sensing hydrogels for the inducible release of biopharmaceuticals. | 2008 Oct |
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Responsive hydrogels for label-free signal transduction within biosensors. | 2010 |
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Antibiotic Resistance in Staphylococcus aureus and Coagulase Negative Staphylococci Isolated from Goats with Subclinical Mastitis. | 2010 |
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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 |
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Biliary efflux transporters involved in the clearance of rosuvastatin in sandwich culture of primary rat hepatocytes. | 2010 Mar |
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Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen. | 2011 Aug |
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Aminopyrazinamides: novel and specific GyrB inhibitors that kill replicating and nonreplicating Mycobacterium tuberculosis. | 2013 Mar 15 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15047534/
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.
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WHO-VATC |
QJ01XX95
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CFR |
21 CFR 526.1696D
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CFR |
21 CFR 526.1590
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NCI_THESAURUS |
C258
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21 CFR 558.415
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CFR |
21 CFR 556.460
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206-146-3
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DB01051
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1974
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NOVOBIOCIN
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C705
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303-81-1
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)