Novobiocin sodium
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 573642

CAS#: 1476-53-5 (Na)

Description: Novobiocin sodium is an antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity.


Chemical Structure

img
Novobiocin sodium
CAS# 1476-53-5 (Na)

Theoretical Analysis

MedKoo Cat#: 573642
Name: Novobiocin sodium
CAS#: 1476-53-5 (Na)
Chemical Formula: C31H35N2NaO11
Exact Mass: 634.21
Molecular Weight: 634.614
Elemental Analysis: C, 58.67; H, 5.56; N, 4.41; Na, 3.62; O, 27.73

Price and Availability

Size Price Availability Quantity
1g USD 215
5g USD 405
10g USD 650
Bulk inquiry

Related CAS #: 303-81-1 (free base)   1476-53-5 (Na)   4309-70-0 (Ca)  

Synonym: Albadry, Albamycin, Novobiocin monosodium salt, Cardelmycin sodium salt, Cathomycin, Inabiocin, Monosodium novobiocin, Novobiocin sodium, Novobiocin monosodium, Novobiocin natrium, Novobiocin sodium salt, Sodium albamycin, Sodium novobiocin, Streptonivicin sodium salt, U 6591, U6591, U-6591, Vulcamycin

IUPAC/Chemical Name: sodium 7-(((2R,3R,4S,5R)-4-(carbamoyloxy)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido)-8-methyl-2-oxo-2H-chromen-4-olate

InChi Key: WWPRGAYLRGSOSU-RNROJPEYSA-M

InChi Code: 1S/C31H36N2O11.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/p-1/t23-,25+,26-,29-;/m1./s1

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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Novobiocin (Albamycin) sodium is a potent and orally active antibiotic. Novobiocin sodium also is a DNA gyrase inhibitor and a heat shock protein 90 (Hsp90) antagonist.
In vitro activity: Novobiocin specifically inhibited the maturation of the heme-regulated eIF2alpha kinase (HRI) in a concentration-dependent manner. Novobiocin induced the dissociation of Hsp90 and Cdc37 from immature HRI, while the Hsp90 cochaperones p23, FKBP52, and protein phosphatase 5 remained associated with immature HRI. Reference: Biochemistry. 2004 Jun 29;43(25):8217-29. https://pubmed.ncbi.nlm.nih.gov/15209518/
In vivo activity: The most effective regimens in animals infected with the amoxicillin-susceptible strain were 200 mg/kg novobiocin and 25 mg/kg amoxicillin, achieving 100% survival and undetectable organisms in the peritoneum. Among mice infected with amoxicillin-resistant S. pneumoniae, 200 mg/kg novobiocin gave the highest protection (90-100% survivors), followed by 200mg/kg amoxicillin (60-100%), 100 mg/kg novobiocin (50-87.5%) and 50 mg/kg amoxicillin (14.3-25%). Reference: Int J Antimicrob Agents. 2010 Jun;35(6):544-9. https://pubmed.ncbi.nlm.nih.gov/20303716/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 65.0 102.42
Ethanol 100.0 157.58
Water 83.3 131.31

Preparing Stock Solutions

The following data is based on the product molecular weight 634.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Singh G, Jayanarayan KG, Dey CS. Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. Mol Biochem Parasitol. 2005 May;141(1):57-69. doi: 10.1016/j.molbiopara.2005.01.014. PMID: 15811527. 2. Yun BG, Huang W, Leach N, Hartson SD, Matts RL. Novobiocin induces a distinct conformation of Hsp90 and alters Hsp90-cochaperone-client interactions. Biochemistry. 2004 Jun 29;43(25):8217-29. doi: 10.1021/bi0497998. PMID: 15209518. 3. Llanos MA, Enrique N, Sbaraglini ML, Garofalo FM, Talevi A, Gavernet L, Martín P. Structure-Based Virtual Screening Identifies Novobiocin, Montelukast, and Cinnarizine as TRPV1 Modulators with Anticonvulsant Activity In Vivo. J Chem Inf Model. 2022 Jun 27;62(12):3008-3022. doi: 10.1021/acs.jcim.2c00312. Epub 2022 Jun 13. PMID: 35696534. 4. Rodríguez-Cerrato V, Del Prado G, Huelves L, Naves P, Ruiz V, García E, Ponte C, Soriano F. Comparative efficacy of novobiocin and amoxicillin in experimental sepsis caused by beta-lactam-susceptible and highly resistant pneumococci. Int J Antimicrob Agents. 2010 Jun;35(6):544-9. doi: 10.1016/j.ijantimicag.2010.02.007. Epub 2010 Mar 19. PMID: 20303716.
In vitro protocol: 1. Singh G, Jayanarayan KG, Dey CS. Novobiocin induces apoptosis-like cell death in topoisomerase II over-expressing arsenite resistant Leishmania donovani. Mol Biochem Parasitol. 2005 May;141(1):57-69. doi: 10.1016/j.molbiopara.2005.01.014. PMID: 15811527. 2. Yun BG, Huang W, Leach N, Hartson SD, Matts RL. Novobiocin induces a distinct conformation of Hsp90 and alters Hsp90-cochaperone-client interactions. Biochemistry. 2004 Jun 29;43(25):8217-29. doi: 10.1021/bi0497998. PMID: 15209518.
In vivo protocol: 1. Llanos MA, Enrique N, Sbaraglini ML, Garofalo FM, Talevi A, Gavernet L, Martín P. Structure-Based Virtual Screening Identifies Novobiocin, Montelukast, and Cinnarizine as TRPV1 Modulators with Anticonvulsant Activity In Vivo. J Chem Inf Model. 2022 Jun 27;62(12):3008-3022. doi: 10.1021/acs.jcim.2c00312. Epub 2022 Jun 13. PMID: 35696534. 2. Rodríguez-Cerrato V, Del Prado G, Huelves L, Naves P, Ruiz V, García E, Ponte C, Soriano F. Comparative efficacy of novobiocin and amoxicillin in experimental sepsis caused by beta-lactam-susceptible and highly resistant pneumococci. Int J Antimicrob Agents. 2010 Jun;35(6):544-9. doi: 10.1016/j.ijantimicag.2010.02.007. Epub 2010 Mar 19. PMID: 20303716.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Mandler MD, Baidin V, Lee J, Pahil KS, Owens TW, Kahne D. Novobiocin Enhances Polymyxin Activity by Stimulating Lipopolysaccharide Transport. J Am Chem Soc. 2018 Jun 6;140(22):6749-6753. doi: 10.1021/jacs.8b02283. Epub 2018 May 16. PubMed PMID: 29746111; PubMed Central PMCID: PMC5990483.

2: May JM, Owens TW, Mandler MD, Simpson BW, Lazarus MB, Sherman DJ, Davis RM, Okuda S, Massefski W, Ruiz N, Kahne D. The Antibiotic Novobiocin Binds and Activates the ATPase That Powers Lipopolysaccharide Transport. J Am Chem Soc. 2017 Dec 6;139(48):17221-17224. doi: 10.1021/jacs.7b07736. Epub 2017 Nov 22. PubMed PMID: 29135241; PubMed Central PMCID: PMC5735422.

3: Dlugosz A, Janecka A. Novobiocin Analogs as Potential Anticancer Agents. Mini Rev Med Chem. 2017;17(9):728-733. doi: 10.2174/1389557516666161223155525. Review. PubMed PMID: 28019639.

4: Chen W, Wang D, Zhou W, Sang H, Liu X, Ge Z, Zhang J, Lan L, Yang CG, Chen H. Novobiocin binding to NalD induces the expression of the MexAB-OprM pump in Pseudomonas aeruginosa. Mol Microbiol. 2016 Jun;100(5):749-58. doi: 10.1111/mmi.13346. Epub 2016 Mar 16. PubMed PMID: 26844397.

5: Audisio D, Methy-Gonnot D, Radanyi C, Renoir JM, Denis S, Sauvage F, Vergnaud-Gauduchon J, Brion JD, Messaoudi S, Alami M. Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors. Eur J Med Chem. 2014 Aug 18;83:498-507. doi: 10.1016/j.ejmech.2014.06.067. Epub 2014 Jun 28. PubMed PMID: 24992077.