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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/09/04 04:31:17」(JST)

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Spiramycin is a macrolide antibiotic. It is used to treat toxoplasmosis and various other infections of soft tissues. Although used in Europe, Canada and Mexico^[1], spiramycin is still considered an experimental drug in the United States, but can sometimes be obtained by special permission from the FDA for toxoplasmosis in the first trimester of pregnancy.^[2]

Spiramycin has been used in Europe since the year 2000 under the trade name "Rovamycine", produced by Rhone-Poulenc Rorer and Famar Lyon, France and Eczacibasi Ilae, Turkey. It also goes under the name Rovamycine in Canada (distributed by OdanLaboratories), where it is mostly marketed to dentists for mouth infections.

Spiramycin is a 16-membered ring macrolide (antibiotic). It was discovered in 1952 as a product of Streptomyces ambofaciens. As a preparation for oral administration it has been used since 1955, in 1987 also the parenteral form was introduced into practice. The antibacterial action involves inhibition of protein synthesis in the bacterial cell during translocation. Resistance to spiramycin can develop by several mechanisms and its prevalence is to a considerable extent proportional to the frequency of prescription in a given area. The antibacterial spectrum comprises Gram-positive cocci and rods, Gram-negative cocci and also Legionellae, mycoplasmas, chlamydiae, some types of spirochetes, Toxoplasma gondii and Cryptosporidium sp., Enterobacteria, pseudomonads and pathogenic moulds are resistant. Its action is mainly bacteriostatic, on highly sensitive strains it exerts a bactericide action. As compared with erythromycin, it is in vitro weight for weight 5 to 20 less effective, an equipotential therapeutic dose is, however, only double. This difference between the effectiveness in vitro and in vivo is explained above all by the great affinity of spiramycin to tissues where it achieves concentrations many times higher than serum levels. An important part is played also by the slow release of the antibiotic from the tissue compartment, the marked action on microbes in sub-inhibition concentrations and the relatively long persisting post-antibiotic effect. Its great advantage is the exceptionally favourable tolerance-gastrointestinal and general. It is available for parenteral and oral administration

References

^ Spiramycin advanced consumer information | Drugs.com
^ Toxoplasmosis at MayoClinic.com

UpToDate Contents

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1. トキソプラズマ症と妊娠 toxoplasmosis and pregnancy
2. 抗原虫治療 antiprotozoal therapies
3. マクロライド系剤、アミノグリコシド、テトラサイクリン、クリンダマイシン、および
メトロニダゾールに対する過敏反応 hypersensitivity reactions to macrolides aminoglycosides tetracyclines clindamycin and metronidazole
4. クリプトスポリジウム症の治療および予防 treatment and prevention of cryptosporidiosis

English Journal

Post-PKS tailoring steps of the spiramycin macrolactone ring in Streptomyces ambofaciens.

Nguyen HC, Darbon E, Thai R, Pernodet JL, Lautru S.SourceUniversité Paris-Sud, Institut de Génétique et Microbiologie (UMR 8621), F-91405 Orsay Cedex, France.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2013 May 28. [Epub ahead of print]
Spiramycins are clinically important 16-membered macrolide antibiotics produced by Streptomyces ambofaciens. Biosynthetic studies have established that the earliest lactonic intermediate in spiramycin biosynthesis, the macrolactone platenolide I, is synthesized by a type I modular polyketide synthas
PMID 23716060

Toxoplasma seroconversion with negative or transient immunoglobulin M in pregnant women: myth or reality? A French multicentre retrospective study.

Fricker-Hidalgo H, Cimon B, Chemla C, Darde ML, Delhaes L, L'ollivier C, Godineau N, Houze S, Paris L, Quinio D, Robert-Gangneux F, Villard O, Villena I, Candolfi E, Pelloux H; the network from the French National Reference Center for Toxoplasmosis.SourceLaboratoire de Parasitologie-Mycologie, Université Joseph Fourier, Grenoble 1 et Centre Hospitalier Universitaire A. Michallon, BP 217, 38043 Grenoble Cedex, France.
Journal of clinical microbiology.J Clin Microbiol.2013 Apr 24. [Epub ahead of print]
Classically, Toxoplasma infection is associated with high levels of specific IgM antibody detection and a rise in specific IgG in the 1-3 following weeks. Atypical IgG seroconversion, without IgM detection or with transient IgM levels, has been exceptionally described during serologic follow-up of s
PMID 23616461

Hapten modification approach for switching immunoassay specificity from selective to generic.

Burkin MA, Galvidis IA.SourceDepartment of Hybridomas, Mechnikov Research Institute for Vaccines and Sera, Russian Academy of Medical Sciences, Moscow 105064, Russia. burma68@yandex.ru
Journal of immunological methods.J Immunol Methods.2013 Feb 28;388(1-2):60-7. doi: 10.1016/j.jim.2012.12.002. Epub 2012 Dec 9.
The cross-reactivity profile of polyclonal antibodies against a low molecular weight analyte is strongly influenced by design of the coating or enzyme-linked hapten. The hapten modification effect on immunoassay specificity was studied. Heterology in hapten type and linking method were applied. The
PMID 23234756

Japanese Journal

Simultaneous multiresidue determination of metronidazole and spiramycin in fish muscle using high performance liquid chromatography with UV detection

MAHER Hadir M.,YOUSSEF Rasha M.,KHALIL Riad H.,EL-BAHR Sabry M.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 876(2), 175-181, 2008-12-15
NAID 10028010790

食肉中に残留する抗菌性物質の微生物学的簡易検査法

堀江正一,小林晴美,石井里枝,井部明広,藤田和弘,丹野憲二,中澤裕之
食品衛生学雑誌 49(3), 168-176, 2008-06-25
畜産食品中に残留するペニシリン系抗生物質(PCs)，セファロスポリン系抗生物質(CEs)，テトラサイクリン系抗生物質(TCs)，マクロライド系抗生物質(MLs)，キノロン系抗菌剤(QNs)などを中心とした，より多くの抗菌性物質を同時に検出できる微生物学的試験法を検討した．食肉からメタノールでホモジナイズ抽出し，10分間遠心分離後，その上清を微生物学的試験法に供した．市販芽胞菌を含めた4種の検査用平 …
NAID 10024453643

4"'-N-Demethylspiramycin Derivatives : Synthesis and Evaluation of Effectiveness against Drug-resistant Bacteria

SUNAZUKA Toshiaki,SHUDO Hiroko,NAGAI Kenichiro,YOSHIDA Kiminari,YAMAGUCHI Yukie,HANAKI Hideaki,OMURA Satoshi
Journal of antibiotics = An International Journal Devoted to Research on Bioactive Microbial Products 61(3), 175-184, 2008-03-25
NAID 10021927516

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★リンクテーブル★

リンク元	「スピラマイシン」「SPM」
拡張検索	「acetylspiramycin」

「スピラマイシン」

Spiramycin
Systematic (IUPAC) name
	(4R,5S,6R,7R,9R,10R,11E,13E,16R)-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-9,16-dimethyl-5-methoxy-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranosyl)-3-(dimethylamino)-α-D-glucopyranoside
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	8025-81-8
ATC code	J01FA02 QJ51FA02
PubChem	CID 5356392
ChemSpider	4512090
UNII	71ODY0V87H
KEGG	D05908
ChEMBL	CHEMBL1256397
NIAID ChemDB	007350
Synonyms	2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,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
Chemical data
Formula	C43H74N2O14
Mol. mass	843.053 g/mol
	SMILES O=CCC4C(OC2OC(C(OC1OC(C)C(O)C(O)(C)C1)C(N(C)C)C2O)C)C(OC)C(O)CC(=O)OC(C)C\C=C\C=C\C(OC3OC(C)C(N(C)C)CC3)C(C)C4;
	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+ ; Key:ACTOXUHEUCPTEW-OBURPCBNSA-N ;
Physical data
Solubility in water	Insoluble in water; Very soluble in acetonitrile and methanol; Almost completely(>99.5) in ethanol. mg/mL (20 °C)
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