Viranamycin A
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| Category | Antibiotics |
| Catalog number | BBF-02964 |
| CAS | 139595-03-2 |
| Molecular Weight | 764.94 |
| Molecular Formula | C41H64O13 |
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Description
It is produced by the strain of Str. sp. CH 41. It can inhibit the growth of murine leukemia cell P388 with IC50 of 5.8 ng/mL, and it can also inhibit KB human multi-squamous cell carcinoma cells with IC50 of 6.4 ng/mL.
Specification
| Synonyms | Concanamycin A, 23-O-(3-carboxy-1-oxo-2-propenyl)-23-O-de[4-O-(aminocarbonyl)-2,6-dideoxy-b-D-arabino-hexopyranosyl]-25-de(1-propenyl)-25-methyl- |
| IUPAC Name | (E)-4-[(2R,4R,5S,6R)-2-[(2R,3R,4R)-4-[(2R,3R,4E,6E,9S,10R,11S,12R,13S,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl]-2-hydroxy-5,6-dimethyloxan-4-yl]oxy-4-oxobut-2-enoic acid |
| Canonical SMILES | CCC1C(C(CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C2(CC(C(C(O2)C)C)OC(=O)C=CC(=O)O)O)O)OC)C)C)O |
| InChI | InChI=1S/C41H64O13/c1-12-30-36(45)24(4)18-22(2)14-13-15-31(50-10)39(53-40(48)32(51-11)20-23(3)19-25(5)37(30)46)27(7)38(47)28(8)41(49)21-33(26(6)29(9)54-41)52-35(44)17-16-34(42)43/h13-17,19-20,24-31,33,36-39,45-47,49H,12,18,21H2,1-11H3,(H,42,43)/b15-13+,17-16+,22-14+,23-19+,32-20-/t24-,25-,26-,27+,28+,29+,30-,31+,33+,36+,37+,38+,39+,41+/m0/s1 |
| InChI Key | FFXNCZHMXIHYJQ-SXEKAWBDSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 887.4±65.0°C at 760 mmHg |
| Melting Point | 89-90°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Isolation and structural elucidation of new 18-membered macrolide antibiotics, viranamycins A and B
Y Hayakawa, K Takaku, K Furihata, K Nagai, H Seto J Antibiot (Tokyo). 1991 Dec;44(12):1294-9. doi: 10.7164/antibiotics.44.1294.
Two cytotoxic antibiotics, designated viranamycins A and B, were isolated from the culture broth of Streptomyces sp. CH41. Their structures were elucidated as new 18-membered macrolides related to virustomycin A and concanamycin A from NMR spectral analysis. Viranamycins A and B inhibited the growth of P388 mouse leukemia and KB human squamous-cell-carcinoma cells.
2. Utilising animal models to evaluate oseltamivir efficacy against influenza A and B viruses with reduced in vitro susceptibility
Rubaiyea Farrukee, Celeste Ming-Kay Tai, Ding Yuan Oh, Danielle E Anderson, Vithiagaran Gunalan, Martin Hibberd, Gary Yuk-Fai Lau, Ian G Barr, Veronika von Messling, Sebastian Maurer-Stroh, Aeron C Hurt PLoS Pathog. 2020 Jun 18;16(6):e1008592. doi: 10.1371/journal.ppat.1008592. eCollection 2020 Jun.
The neuraminidase (NA) inhibitor (NAI) oseltamivir (OST) is the most widely used influenza antiviral drug. Several NA amino acid substitutions are reported to reduce viral susceptibility to OST in in vitro assays. However, whether there is a correlation between the level of reduction in susceptibility in vitro and the efficacy of OST against these viruses in vivo is not well understood. In this study, a ferret model was utilised to evaluate OST efficacy against circulating influenza A and B viruses with a range of in vitro generated 50% inhibitory concentrations (IC50) values for OST. OST efficacy against an A(H1N1)pdm09 and an A(H1N1)pdm09 virus with the H275Y substitution in neuraminidase was also tested in the macaque model. The results from this study showed that OST had a significant impact on virological parameters compared to placebo treatment of ferrets infected with wild-type influenza A viruses with normal IC50 values (~1 nM). However, this efficacy was lower against wild-type influenza B and other viruses with higher IC50 values. Differing pathogenicity of the viruses made evaluation of clinical parameters difficult, although some effect of OST in reducing clinical signs was observed with influenza A(H1N1) and A(H1N1)pdm09 (H275Y) viruses. Viral titres in macaques were too low to draw conclusive results. Analysis of the ferret data revealed a correlation between IC50 and OST efficacy in reducing viral shedding but highlighted that the current WHO guidelines/criteria for defining normal, reduced or highly reduced inhibition in influenza B viruses based on in vitro data are not well aligned with the low in vivo OST efficacy observed for both wild-type influenza B viruses and those with reduced OST susceptibility.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
