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Acetylspiramycin

Acetylspiramycin - CAS 24916-51-6

Catalog number: BBF-03461

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Catalog Number BBF-03461
CAS 24916-51-6
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.
Molecular Formula C45H76N2O15
Molecular Weight 885.09
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Mycobacteria
Synonyms Spiramycin II; 9-O-[(2R,5S,6R)-5-(Dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-3-acetate-leucomycin V; foromacidin B; spiramycin 2; spiramycin B; Leucomycin V, 9-O-[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]-3-acetate
IUPAC Name [(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-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] acetate
Canonical SMILES CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)OC(=O)C)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/C45H76N2O15/c1-25-22-31(20-21-48)41(62-44-39(51)38(47(10)11)40(28(4)58-44)61-37-24-45(7,53)43(52)29(5)57-37)42(54-12)34(59-30(6)49)23-35(50)55-26(2)16-14-13-15-17-33(25)60-36-19-18-32(46(8)9)27(3)56-36/h13-15,17,21,25-29,31-34,36-44,51-53H,16,18-20,22-24H2,1-12H3/b14-13+,17-15+/t25-,26-,27-,28-,29+,31+,32+,33+,34-,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1
InChI Key ZPCCSZFPOXBNDL-ZSTSFXQOSA-N
Boiling Point 916.7±65.0°C (Predicted)
Melting Point 130-133°C
Purity ≥98%
Density 1.21±0.1 g/cm3 (Predicted)
Solubility Slightly soluble in Methanol (Sonicated, Heated), DMSO
Appearance White Powder
Storage Store at-20°C
1.Fetal therapy of severe symptomatic toxoplasmosis using azithromycin.
Tamaru S1, Kikuchi A, Takagi K, Wakamatsu M, Horikoshi T, Ogiso Y. J Obstet Gynaecol Res. 2011 Jul;37(7):953-7. doi: 10.1111/j.1447-0756.2010.01459.x. Epub 2011 Mar 31.
Severe symptomatic fetal toxoplasmosis rarely occurs after the maternal primary infection of Toxoplasma gondii. We herein report our experience of fetal therapy of symptomatic toxoplasmosis using azithromycin. Ultrasound assessment at 23 weeks' gestation revealed fetal ascites, cardiac effusion, cardiomegaly, enlarged lateral ventricles and thickened placenta. Serum Toxoplasma gondii antibody titer was ×81,920. Toxoplasma immunoglobulin M was 2.4 index (normal, <0.8 index), and immunoglobulin G was ≥240 IU/mL (normal, <6 IU/mL). Maternal oral administration of azithromycin in addition to sulfadoxine, pyrimethamine and acetylspiramycin was conducted. Spontaneous vaginal delivery occurred at 32 weeks and a male infant weighing 2036 g was born. Hepatosplenomegaly, chorioretinitis, hydrocephalus, intracranial calcifications, ascites, and meningitis were confirmed after birth. The infant underwent therapy with pyrimethamine and sulfadiazine.
2.A case of recurrence of congenital ocular toxoplasmosis with frosted branch angiitis (ocular toxoplasmosis with frosted branch angiitis).
Suzuki T1, Onouchi H, Nakagawa Y, Oohashi H, Kaiken H, Kawai K. Tokai J Exp Clin Med. 2010 Dec 20;35(4):122-5.
PURPOSE: To describe a case of recurrence of congenital ocular toxoplasmosis with frosted branch angiitis.
3.[Impurity profiling of macrolide antibiotics by liquid chromatography-mass spectrometry].
Wang MJ1, Hu CQ. Yao Xue Xue Bao. 2013 May;48(5):642-7.
Macrolide antibiotics are broad-spectrum, with activity against a range of Gram-positive, Gram-negative organisms and some anaerobes. The components of macrolide antibiotics are generally complicated. Therefore, it is very important to establish impurity profiles of these antibiotics to ensure their safety and process control. Compared with classical methods, the liquid chromatography-mass spectrometry method is particularly advantageous to characterize minor components at trace levels in terms of sensitivity, efficiency and selectivity, thus more and more widely used in establishments of impurity profiles. In this study, the general approaches to characterize minor components in complex pharmaceutical matrix, fragmentation pathways of 14- and 16-membered macrolide antibiotics and the establishment of the impurity profile of acetylspiramycin were given to provide valuable enlightenments to establish the impurity profiles of pharmaceutical products.
4.Presumed toxoplasmic central retinal artery occlusion and multifocal retinitis with perivascular sheathing.
Arai H1, Sakai T1, Okano K1, Aoyagi R1, Imai A2, Takase H2, Mochizuki M2, Tsuneoka H1. Clin Ophthalmol. 2014 Apr 23;8:789-92. doi: 10.2147/OPTH.S58669. eCollection 2014.
Central retinal artery occlusion (CRAO) and multifocal retinitis with perivascular sheathing are rare in ocular toxoplasmosis. We report a case of toxoplasmic CRAO and multifocal retinitis with perivascular sheathing. A healthy 83-year-old male developed left panuveitis. Funduscopic examination of the left eye showed a swollen optic disc and sheathing of the retinal artery with a dense vitreous haze and a white retinal lesion. Serum anti-toxoplasma antibodies were positive in a latex agglutination assay. Vitrectomy was performed to improve visualization of the retinal lesions and for examination of causative microorganisms. A postoperative fundus examination revealed CRAO with optic disc involvement and multifocal retinitis with perivascular sheathing. Qualitative multiplex polymerase chain reaction detected the Toxoplasma gondii B1 gene in ocular fluid from both the aqueous and vitreous humor. The presumed diagnosis of ocular toxoplasmosis was made and treatment was started with prednisone and acetylspiramycin with subsequent improvement.
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