ジョサマイシン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/10/27 11:06:30」(JST)
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Josamycin
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Systematic (IUPAC) name |
(2S,3S,4R,6S) -6- {[(2R,3S,4R,5R,6S) -6- {[(4R,5S,6S,7R,9R,10R,11E,13E,16R) -4- (acetyloxy)-10-hydroxy-5-methoxy-9, 16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11, 13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2, 4-dimethyloxan-3-yl 3-methylbutanoate |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
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Identifiers |
CAS number |
16846-24-5 Y |
ATC code |
J01FA07 |
PubChem |
CID 5284579 |
DrugBank |
DB01321 |
ChemSpider |
4447629 Y |
UNII |
HV13HFS217 Y |
KEGG |
D01235 Y |
ChEBI |
CHEBI:31739 N |
ChEMBL |
CHEMBL224436 N |
PDB ligand ID |
JOS (PDBe, RCSB PDB) |
Chemical data |
Formula |
C42H69NO15 |
Mol. mass |
827.995 g/mol |
SMILES
- O=CC[C@H]3C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@H](OC(=O)C[C@@H](OC(=O)C)C(OC)[C@H]3O[C@@H]2O[C@@H]([C@@H](O[C@@H]1O[C@H]([C@@H](OC(=O)CC(C)C)[C@](O)(C1)C)C)[C@H](N(C)C)[C@H]2O)C)C
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InChI
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InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39?,40-,41+,42-/m1/s1 Y
Key:XJSFLOJWULLJQS-HTYUZQQASA-N Y
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N (what is this?) (verify) |
Josamycin is a macrolide antibiotic. It is synthesized from strains of Streptomyces narbonensis var. josamyceticus var. nova
Currently sold in various countries.
Brand examples are:
Europe: Josalid, Josacine, Iosalide, Josamina. Russia: Wilprafen (Вильпрафен). Japan: Josamy.
Adverse effects
There has been a case report of oedema of the feet.[1]
References
- ^ Bosch, X.; Pedrol, E.; Casado, X.; Urbano-Marquez, A. (1993). "Josamycin-induced pedal oedema" (pdf). British Medical Journal (Clinical research ed.) 307 (6895): 26. doi:10.1136/bmj.307.6895.26-a. PMC 1678472. PMID 8343666. edit
Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)
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30S |
Aminoglycosides
(initiation inhibitors) |
-mycin (Streptomyces) |
- Streptomycin#
- Dihydrostreptomycin
- Neomycin#
- Framycetin
- Paromomycin
- Ribostamycin
- Kanamycin#
- Amikacin
- Arbekacin
- Bekanamycin
- Dibekacin
- Tobramycin
- Spectinomycin#
- Hygromycin B
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-micin (Micromonospora) |
- Gentamicin#
- Netilmicin
- Sisomicin
- Isepamicin
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Tetracycline antibiotics
(tRNA binding) |
Tetracyclines |
- Doxycycline#
- Chlortetracycline
- Clomocycline
- Demeclocycline
- Lymecycline
- Meclocycline
- Metacycline
- Minocycline
- Oxytetracycline
- Penimepicycline
- Rolitetracycline
- Tetracycline
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Glycylcyclines |
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50S |
Oxazolidinone
(initiation inhibitors) |
- Eperezolid
- Linezolid
- Posizolid
- Radezolid
- Ranbezolid
- Sutezolid
- Tedizolid
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Peptidyl transferase |
Amphenicols |
- Chloramphenicol#
- Azidamfenicol
- Thiamphenicol
- Florfenicol
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Pleuromutilins |
- Retapamulin
- Tiamulin
- Valnemulin
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MLS (transpeptidation/translocation) |
Macrolides |
- Azithromycin#
- Clarithromycin
- Dirithromycin
- Erythromycin#
- Flurithromycin
- Josamycin
- Midecamycin
- Miocamycin
- Oleandomycin
- Rokitamycin
- Roxithromycin
- Spiramycin
- Troleandomycin
- Tylosin
- Ketolides
- Telithromycin
- Cethromycin
- Solithromycin†
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Lincosamides |
- Clindamycin#
- Lincomycin
- Pirlimycin
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Streptogramins |
- Pristinamycin
- Quinupristin/dalfopristin
- Virginiamycin
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EF-G |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- Genital Mycoplasma infections and their resistance phenotypes in an African setting.
- Kouegnigan Rerambiah L1, Ndong JC, Medzegue S, Elisee-Ndam M, Djoba Siawaya JF.
- European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology.Eur J Clin Microbiol Infect Dis.2015 Jun;34(6):1087-90. doi: 10.1007/s10096-015-2326-9. Epub 2015 Jan 29.
- We investigated the antimicrobial susceptibilities of mycoplasmas in Gabonese men and women. A total of 1,332 men and women were included in the study. Sperm, urine, ureteral or vaginal swabs were collected from the subjects. Mycoplasmas identification and antimicrobial susceptibility to azithromyci
- PMID 25630539
- Occurrence of erythromycin residues in sheep milk. Validation of an analytical method.
- García-Mayor MA1, Paniagua-González G1, Soledad-Rodríguez B2, Garcinuño-Martínez RM3, Fernández-Hernando P1, Durand-Alegría JS1.
- Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2015 Apr;78:26-32. doi: 10.1016/j.fct.2014.12.020. Epub 2015 Jan 28.
- The paper describes a new and selective analytical sample treatment for quantitative extraction and preconcentration of erythromycin in presence of other macrolide antibiotics in sheep milk samples. The methodology is based on the use of a molecular imprinted polymer (MIP) employed as solid phase ex
- PMID 25637760
- Ureaplasma: current perspectives.
- Kokkayil P, Dhawan B1.
- Indian journal of medical microbiology.Indian J Med Microbiol.2015 Apr-Jun;33(2):205-14. doi: 10.4103/0255-0857.154850.
- Ureaplasma species are the most prevalent genital Mycoplasma isolated from the urogenital tract of both men and women. Ureaplasma has 14 known serotypes and is divided into two biovars- Ureaplasma parvum and Ureaplasma urealyticum. The organism has several genes coding for surface proteins, the most
- PMID 25865969
Japanese Journal
- Effects of macrolides on antigen-induced increases in cough reflex sensitivity in guinea pigs
- Tokuda Akira,Ohkura Noriyuki,Fujimura Masaki,Furusho Shiho,Abo Miki,Katayama Nobuyuki
- Pulmonary Pharmacology and Therapeutics 23(1), 55-61, 2010-02
- … The 14-, 15- or 16-membered macrolides (erythromycin, azythromycin, or josamycin, respectively) were given intraperitoneally every 12 h after the antigen challenge. … Results: The antigen-induced increase in the number of coughs elicited by capsaicin inhalation was significantly reduced by treatments with erythromycin and azythromycin, but not with josamycin. …
- NAID 120002061088
- Determination of josamycin in rat plasma by capillary electrophoresis coupled with post-column electrochemiluminescence detection
- DENG Biyang,KANG Yanhui,LI Xianfeng,XU Qiumei
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 859(1), 125-130, 2007-11-01
- NAID 10027466026
- 高速液体クロマトグラフィー/質量分析法による乳中のマクロライド系抗生物質の定量(<特集>若手研究者の初論文)
- 竹上 晴美,堀江 正一,中澤 裕之
- 分析化学 55(9), 651-659, 2006-09-05
- 高速液体クロマトグラフ/質量分析計(LC/MS)を用いた簡易かつ感度の高い乳中のマクロライド系抗生物質,具体的にはエリスロマシン,オレアンドマイシン,キタサマイシン,ジョサマイシン,ミロサマイシン,ネオスピラマイシン,スピラマイシン,チルミコシン及びタイロシンの同時分析法を検討した.試料の前処理には抽出にアセトニトリルを採用し,ヘキサンによる液液抽出によりクリーンアップを行った.高速液体クロマトグ …
- NAID 110004833099
Related Links
- Josamycin [JM] ジョサマイシン, マクロライド系 1. 商品名 先発品 ジョサマイシン錠50mg/ジョサマイシン錠200mg 【アステラス製薬, 日医工】 ジョサマイシロップ3% 【アステラス製薬, 日医工】 ジョサマイドライシロップ10% 【アステラス ...
- Sigma-Aldrich offers Sigma-59983, Josamycin for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Packaging Bottomless glass bottle. Contents are inside inserted ...
Related Pictures
★リンクテーブル★
[★]
- 英
- macrolide antibiotic macrolide antibiotics, macrolides, MLs
- 同
- マクロライド系抗生物質 ←厳密には違うが、多くの人が間違って使っている
- 関
- 抗菌薬
特徴
- 抗菌スペクトルが広い
- 静菌的に作用
- 大きな環状構造を有する。14員環-16員環
- タンパク質合成阻害薬
- 抗生物質としての作用の他に、抗炎症作用を有するらしい
- 炎症の抑制 ex.びまん性汎細気管支炎
構造
- http://www.sigmaaldrich.com/life-science/life-science-catalog/product-catalog.html?TablePage=14572877
- Macrolide antibiotics contain a many-membered lactone ring (14-membered rings for erythromycin and clarithromycin and a 15-membered ring for azithromycin) to which are attached one or more deoxy sugars. Clarithromycin differs from erythromycin only by methylation of the hydroxyl group at the 6 position, and azithromycin differs by the addition of a methyl-substituted nitrogen atom into the lactone ring. These structural modifications improve acid stability and tissue penetration and broaden the spectrum of activity.(GOO. chapter 46)
作用機序
- inhibit bacterial protein synthesis by reacting with the 50s ribosomal subunit and preventing the release of the uncharged tRNA.
薬理作用
動態
抗菌スペクトル
- ペニシリンより広い抗菌スペクトル
- グラム陽性球菌、グラム陰性球菌、グラム陰性桿菌、スピロヘータ、一部のリケッチア、ウイルス
適応
- マイコプラズマ肺炎、クラミジア感染症、カンピロバクター腸炎、レジオネラ症
- びまん性汎細気管支炎:14員環マクロライドのみ
- URIs, pneumonias, STD
注意
禁忌
副作用
- 悪心、嘔吐、消化器の蠕動を促進
- テオフィリン
- 喘息の治療薬。CYP3A4で代謝される。中毒域と治療域がちかいので注意する
マクロライド系抗菌薬
14員環
15員環
16員環
14員環 (ケトライド系抗菌薬)
有効性 (SMB.147)
- ○:殺菌的、△静菌的
[★]
- 英
- josamycin JM
- ラ
- josamycinum
- 化
- プロピオン酸ジョサマイシン josamycin propionate
- 商
- ジョサマイシン、ジョサマイ
- 関
- 抗菌薬
[★]
[★]