Spiramycin I
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| Category | Antibiotics |
| Catalog number | BBF-03460 |
| CAS | 24916-50-5 |
| Molecular Weight | 843.05 |
| Molecular Formula | C43H74N2O14 |
| Purity | ≥97% |
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Description
It is a macrolide antibiotic produced by the strain of Str. ambofaciens. It has strong anti-gram-positive bacteria activity, but has weak anti-Gram-negative bacteria and mycobacteria activity. Its antibacterial activity is close to other components. It has partial cross-resistance with erythromycin, carbomycin and picromycin. Its activity is stronger in alkaline condition, and it is more active in vivo than in vitro. It is also effective against scrub typhus fever and rickettsia.
Specification
| Synonyms | 9-O-[(2R,5S,6R)-5-(Dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-leucomycin V; Foromacidin A; demycarosylturimycin H; Spiramycin A; 9-O-[[(5S)-5α-(Dimethylamino)tetrahydro-6β-methyl-2H-pyran]-2-yl]-leucomycin V |
| Storage | Store at-20°C |
| IUPAC Name | 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2R,5S,6R)-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-CEUOBAOPSA-N |
Properties
| Appearance | Amorphous |
| Application | Anti-bacterial agents; coccidiostats |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Mycobacteria |
| Boiling Point | 913.7±65.0°C (Predicted) |
| Melting Point | 134-137°C |
| Density | 1.21±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. A fresh look at the role of spiramycin in preventing a neglected disease: meta-analyses of observational studies
Jose G Montoya, Rima McLeod, Katherine Laessig, Elizabeth Drake-Shanahan, Mir Sohail Fazeli, Akbar Akbary, Sophie S Yoon, Gaye Siliman, Chengyue Zhu Eur J Med Res . 2021 Dec 11;26(1):143. doi: 10.1186/s40001-021-00606-7.
Purpose:We aimed to investigate the effect of antepartum treatment with spiramycin with or without subsequent pyrimethamine-sulfonamide-folinic acid, compared to no treatment, on the rate of mother-to-child transmission (MTCT) of Toxoplasma gondii (T. gondii) and incidence/severity of sequelae in the offspring.Methods:Embase and PubMed were searched for literature on spiramycin in pregnant women suspected/diagnosed with T. gondii infection. Meta-analyses were performed using random-effects model.Results:Thirty-three studies (32 cohorts and 1 cross-sectional study), with a total of 15,406 mothers and 15,250 offspring, were pooled for analyses. The MTCT rate for all treated patients was significantly lower than the untreated [19.5% (95% CI 14-25.5%) versus 50.7% (95% CI 31.2-70%), p < 0.001]. The transmission rate in patients on spiramycin monotherapy was also significantly lower than untreated [17.6% (95% CI 9.9-26.8%) versus 50.7% (95% CI 31.2-70%), p < 0.001].Conclusion:Results indicate significant reduction in MTCT rates following spiramycin treatment of suspected/diagnosed maternal T. gondii infection.
2. Hydroxylation and hydrolysis: two main metabolic ways of spiramycin I in anaerobic digestion
Lei Shao, Ji-an Li, Daijie Chen, Pei Zhu, Wenbin Liu, Jianbin Zhang, Ju Chu Bioresour Technol . 2014 Feb;153:95-100. doi: 10.1016/j.biortech.2013.11.073.
The anaerobic degradation behaviors of five macrolides including spiramycin I, II, III, midecamycin and josamycin by sludge were investigated. Within 32days, 95% of spiramycin I, II or III was degraded, while the remove rate of midecamycin or josamycin was 75%. SPM I degradation was much higher in nutrition supplementation than that just in sludge. The degradation products and processes of spiramycin I were further characterized. Three molecules, designated P-1, P-2 and P-3 according to their order of occurrence, were obtained and purified. Structural determination was then performed by nuclear magnetic resonance and MS/MS spectra, and data indicated that hydroxylation and hydrolysis were main reactions during the anaerobic digestion of spiramycin I. P-1 is the intermediate of hydroxylation, and P-2 is the intermediate of hydrolysis. P-3 is the final product of the both reaction. This study revealed a hydroxylation and hydrolysis mechanism of macrolide in anaerobic digestion.
3. Pharmacodynamics and pharmacokinetics of spiramycin and their clinical significance
I Brook Clin Pharmacokinet . 1998 Apr;34(4):303-10. doi: 10.2165/00003088-199834040-00003.
The absolute bioavailability of oral spiramycin is generally within the range of 30 to 40%. After a 1 g oral dose, the maximum serum drug concentration was found to be within the range 0.4 to 1.4 mg/L. The tissue distribution of spiramycin is extensive. The volume of distribution is in excess of 300 L, and concentrations achieved in bone, muscle, respiratory tract and saliva exceed those found in serum. The intracellular penetration of spiramycin is also rapid and extensive, with the concentrations in alveolar macrophages 10 to 20 times greater than simultaneous serum concentrations. Spiramycin is less metabolised than some of the other macrolides. The renal excretion of spiramycin is low, with 4 to 20% of the dose being excreted by this route. High concentrations of spiramycin are achieved in bile, which is an important route of elimination. The serum elimination half-life of spiramycin is between 6.2 and 7.7 hours. Of significance to clinicians may be the finding that spiramycin is highly concentrated in the respiratory tract and other tissues and macrophages. The post-antibiotic effect of spiramycin is significant and this effect is more prolonged than that of erythromycin against Staphylococcus aureus. Spiramycin has also been shown to greatly reduce the capacity of strains of Gram-positive cocci to adhere to human buccal cells.
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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 ╳
