Spiramycin
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| Category | Antibiotics |
| Catalog number | BBF-04046 |
| CAS | 8025-81-8 |
| Molecular Weight | 843.05 |
| Molecular Formula | C43H74N2O14 |
| Purity | >98% |
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Description
Spiramycin is a macrolide antibiotic produced by Streptomyces. It is used to treat toxoplasmosis and various other infections of soft tissues.
Specification
| Synonyms | Foromacidin A |
| Storage | Store at -20°C |
| IUPAC Name | 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde |
| Canonical SMILES | CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)O)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)OC4CCC(C(O4)C)N(C)C |
| InChI | InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26?,27?,28?,29+,30?,31-,32+,34?,35?,36?,37?,38?,39+,40+,41?,42?,43?/m1/s1 |
| InChI Key | ACTOXUHEUCPTEW-JMRHEKERSA-N |
| Source | Streptomyces ambofaciens |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | parasites |
| Melting Point | 151°C |
| Solubility | Soluble in ethanol (30 mg/mL), methanol, DMF (30 mg/mL), DMSO (30 mg/mL) |
Reference Reading
1.Fabrication of surface plasmon resonance nanosensor for the selective determination of erythromycin via molecular imprinted nanoparticles.
Sari E1, Üzek R1, Duman M2, Denizli A3. Talanta. 2016 Apr 1;150:607-14. doi: 10.1016/j.talanta.2015.12.043. Epub 2015 Dec 19.
The main objective of this study was to develop a novel surface plasmon resonance (SPR) nanosensor method based on a more rapid and selective determination of erythromycin (ERY) in the aqueous solution. This study is a combination of three techniques, which are miniemulsion polymerization, molecular imprinting and surface plasmon resonance techniques. In the first part, nanoparticles prepared with methacryl groups of functional monomer at surface acted as reactive sites for erythromycin as a template molecule. The molecularly imprinted nanoparticles were characterized by FTIR, SEM and zetasizer. After immobilization of nanoparticles on gold surface of SPR chip, nanosensor was characterized with contact angle measurements. This nanosensor was then used for selective determination of erythromycin. The linearity range and detection limit were obtained as 0.99 (r(2)) and 0.29ppm, respectively. Association kinetic analysis, Scatchard, Langmuir, Freundlich and Freundlich-Langmuir isotherms were applied data.
2.Antimicrobial drug use and risk factors associated with treatment incidence and mortality in Swiss veal calves reared under improved welfare conditions.
Lava M1, Schüpbach-Regula G2, Steiner A1, Meylan M3. Prev Vet Med. 2016 Apr 1;126:121-30. doi: 10.1016/j.prevetmed.2016.02.002. Epub 2016 Feb 5.
Ninety-one Swiss veal farms producing under a label with improved welfare standards were visited between August and December 2014 to investigate risk factors related to antimicrobial drug use and mortality. All herds consisted of own and purchased calves, with a median of 77.4% of purchased calves. The calves' mean age was 29±15days at purchasing and the fattening period lasted at average 120±28 days. The mean carcass weight was 125±12kg. A mean of 58±33 calves were fattened per farm and year, and purchased calves were bought from a mean of 20±17 farms of origin. Antimicrobial drug treatment incidence was calculated with the defined daily dose methodology. The mean treatment incidence (TIADD) was 21±15 daily doses per calf and year. The mean mortality risk was 4.1%, calves died at a mean age of 94±50 days, and the main causes of death were bovine respiratory disease (BRD, 50%) and gastro-intestinal disease (33%). Two multivariable models were constructed, for antimicrobial drug treatment incidence (53 farms) and mortality (91 farms).
3.The prevalence of genotypes that determine resistance to macrolides, lincosamides, and streptogramins B compared with spiramycin susceptibility among erythromycin-resistant Staphylococcus epidermidi
Juda M1, Chudzik-Rzad B1, Malm A1. Mem Inst Oswaldo Cruz. 2016 Mar;111(3):155-60. doi: 10.1590/0074-02760150356.
Coagulase-negative staphylococci, particularly Staphylococcus epidermidis, can be regarded as potential reservoirs of resistance genes for pathogenic strains, e.g., Staphylococcus aureus. The aim of this study was to assess the prevalence of different resistance phenotypes to macrolide, lincosamide, and streptogramins B (MLSB) antibiotics among erythromycin-resistant S. epidermidis, together with the evaluation of genes promoting the following different types of MLSB resistance:ermA, ermB, ermC,msrA, mphC, and linA/A'. Susceptibility to spiramycin was also examined. Among 75 erythromycin-resistantS. epidermidis isolates, the most frequent phenotypes were macrolides and streptogramins B (MSB) and constitutive MLSB (cMLSB). Moreover, all strains with the cMLSB phenotype and the majority of inducible MLSB (iMLSB) isolates were resistant to spiramycin, whereas strains with the MSB phenotype were sensitive to this antibiotic. The D-shape zone of inhibition around the clindamycin disc near the spiramycin disc was found for some spiramycin-resistant strains with the iMLSB phenotype, suggesting an induction of resistance to clindamycin by this 16-membered macrolide.
4.[Fate of ARB and ARGs During Wastewater Treatment Process of Spiramycin Production].
Qin CX, Tong J, Shen PH, Wei YS. Huan Jing Ke Xue. 2015 Sep;36(9):3311-8.
Antibiotic resistant bacteria (ARB) and antibiotic resistance gene(ARG) pose great risk to both environment and human health. This study aimed to investigate the fate of macrolide resistant bacteria, six macrolide resistance genes ermB, ermF, ermX, mefA, ereA, mphB and three transfer elements ISCR1, intIl and Tn916/1545 during wastewater biological treatment processes of spiramycin production. Samples were collected from an antibiotic wastewater treatment station in different seasons. Results showed that the total heterotrophs and Enterococci were mostly removed during wastewater biological treatment, with the reduction of 1. 6-2. 1 logs for total heterotrophs and of 3. 7 logs for Enterococci, respectively. For 94 antibiotic resistant Enterococci individually isolated from four different treatment units including adjusting tank, anaerobic tank, anoxic tank, and aerobic tank, all of these strains showed resistance to spiramycin, azithromycin, erythromycin, and clarithromycin; moreover, the antibiotic resistance rates was not reduced in the effluent.
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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 ╳
