Septamycin Sodium salt
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| Category | Antibiotics |
| Catalog number | BBF-02904 |
| CAS | 55924-40-8 |
| Molecular Weight | 937.13 |
| Molecular Formula | C48H81NaO16 |
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Description
It is a polyether antibiotic produced by the strain of Str. hygroscopicus NRRL 5678. It has anti-bacterial effect and is also effective against some drug-resistant bacteria (Resistance to penicillin, aminoglycoside antibiotics, etc).
Specification
| Related CAS | 54927-63-8 (free acid) |
| Synonyms | Septamycin, monosodium salt |
| IUPAC Name | sodium;(2R)-2-[(2S,3S,4S,5S,6S)-2-hydroxy-6-[[(2R,3R,4R,5S,6R,7R,9S)-2-[(2R,5S)-5-[(2R,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]oxolan-2-yl]-3,7-dimethoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-4-methoxy-5-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-3,5-dimethyloxan-2-yl]propanoate |
| Canonical SMILES | CC1CC(C(OC1C2CCC(O2)C3CCC(O3)C4(C(C(C5(O4)C(C(CC(O5)CC6C(C(C(C(O6)(C(C)C(=O)[O-])O)C)OC)(C)OC7CCC(C(O7)C)OC)OC)C)C)OC)C)(C)O)C.[Na+] |
| InChI | InChI=1S/C48H82O16.Na/c1-24-21-25(2)46(10,51)63-40(24)35-16-15-33(58-35)34-17-19-37(59-34)45(9)42(56-14)28(5)48(64-45)26(3)36(54-12)22-31(60-48)23-38-44(8,62-39-20-18-32(53-11)30(7)57-39)41(55-13)27(4)47(52,61-38)29(6)43(49)50;/h24-42,51-52H,15-23H2,1-14H3,(H,49,50);/q;+1/p-1/t24-,25+,26+,27-,28+,29-,30+,31-,32-,33+,34-,35+,36+,37+,38-,39-,40-,41-,42+,44-,45+,46-,47-,48-;/m0./s1 |
| InChI Key | SIIORNJHEWQPHB-ZBOWIECJSA-M |
Properties
| Appearance | White Crystal |
| Boiling Point | 861.9°C at 760 mmHg |
| Melting Point | 164-166°C |
| Density | 1.20 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Applications of fast atom bombardment mass spectrometry and fast atom bombardment mass spectrometry-mass spectrometry to the maduramicins and other polyether antibiotics
M M Siegel, W J McGahren, K B Tomer, T T Chang Biomed Environ Mass Spectrom. 1987 Jan;14(1):29-38. doi: 10.1002/bms.1200140108.
Fast atom bombardment mass spectrometry (FAB MS) and fast atom bombardment mass spectrometry-mass spectrometry (FAB MS/MS) were used to study the monovalent glycoside polyether antibiotics maduramicin alpha, beta and delta and the maduramicin alpha salts, their derivatives and degradation products. Also, representative compounds from three major classes of polyether antibiotics were studied: the monovalent polyethers, nigericin and monensin A, the divalent polyether lasalocid A and the monovalent glycoside polyethers septamycin, BL580 delta, etheromycin and carriomycin. The respective FAB fragment and decomposition ions were correlated with the known structures. The FAB spectra of all the polyethers contained metal-adduct molecular ions. Protonated molecular ions were absent. All the polyethers having a beta-hemiketal carboxylic acid group produced an abundant ion, often the base peak of the spectra, 62 daltons less than the corresponding metal-adduct molecular ion. The gas phase mechanism proposed for the formation of this fragment ion is an unusual unimolecular reaction which is initiated by an intramolecular proton transfer from the carboxylic acid to the hydroxy group of the beta-hemiketal, and, then followed by the concerted losses of water and carbon dioxide to produce the corresponding polyether olefin.
2. Anticoccidial efficacy and chicken toleration of potent new polyether ionophores. 1. The septamycin relative CP-82,009
A P Ricketts, J P Dirlam, J E Shively Poult Sci. 1992 Oct;71(10):1626-30. doi: 10.3382/ps.0711626.
The anticoccidial activity of the ionophore CP-82,009 against laboratory isolates of four major species of poultry Eimeria was investigated. Parameters of anticoccidial efficacy that were evaluated were control of lesions and weight suppression. At 4 and 5 ppm, CP-82,009 demonstrated broad-spectrum anticoccidial efficacy in battery trials that was equivalent to reference commercial ionophores. When CP-82,009 was fed to uninfected broiler chickens at efficacious dose levels, growth rate and feed efficiency were found to be equivalent to commercial agents over a 21-day period in batteries and over a 49-day period in floor pens. From the present studies, it appears that CP-82,009 is an efficacious anticoccidial that is well tolerated by chickens, and that it ranks among the most potent anticoccidial ionophores described to date.
3. CP-82,009, a potent polyether anticoccidial related to septamycin and produced by Actinomadura sp
J P Dirlam, A M Belton, J Bordner, W P Cullen, L H Huang, Y Kojima, H Maeda, S Nishiyama, J R Oscarson, A P Ricketts, et al. J Antibiot (Tokyo). 1992 Mar;45(3):331-40. doi: 10.7164/antibiotics.45.331.
A new polyether antibiotic CP-82,009 (C49H84O17) was isolated by solvent extraction from the fermentation broth of Actinomadura sp. (ATCC 53676). Following purification by column chromatography and crystallization, the structure of CP-82,009 was elucidated by spectroscopic (NMR and MS) methods. The absolute stereochemistry was determined by a single crystal X-ray analysis of the corresponding rubidium salt. CP-82,009 is among the most potent anticoccidial agents known, effectively controlling the Eimeria species that are the major causative agents of chicken coccidiosis at doses of 5 mg/kg or less in feed. It is also active in vitro against certain Gram-positive bacteria, as well as the spirochete, Serpulina (Treponema) hyodysenteriae.
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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 ╳
