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
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
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/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
65.0 |
102.42 |
| Ethanol |
100.0 |
157.58 |
| Water |
83.3 |
131.31 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
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.
| 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.
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.
