Josamycin (BioDeep_00000002552)

 

Secondary id: BioDeep_00000398723, BioDeep_00001103496

human metabolite blood metabolite Chemicals and Drugs Volatile Flavor Compounds


代谢物信息卡片


(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

化学式: C42H69NO15 (827.4666963999999)
中文名称: 交沙霉素
谱图信息: 最多检出来源 Homo sapiens(blood) 55.56%

分子结构信息

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)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
InChI: 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

描述信息

Josamycin is only found in individuals that have used or taken this drug. It is a macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens. [PubChem]The mechanism of action of macrolides such as Josamycin is via inhibition of bacterial protein biosynthesis by binding reversibly to the subunit 50S of the bacterial ribosome, thereby inhibiting translocation of peptidyl tRNA. This action is mainly bacteriostatic, but can also be bactericidal in high concentrations. Macrolides tend to accumulate within leukocytes, and are therefore actually transported into the site of infection.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01F - Macrolides, lincosamides and streptogramins > J01FA - Macrolides
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
C784 - Protein Synthesis Inhibitor > C261 - Macrolide Antibiotic
C254 - Anti-Infective Agent > C258 - Antibiotic
Same as: D01235
Josamycin (EN-141) is a macrolide antibiotic exhibiting antimicrobial activity against a wide spectrum of pathogens, such as bacteria. The dissociation constant Kd from ribosome for Josamycin is 5.5 nM.

同义名列表

24 个代谢物同义名

(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; Leucomycin V 3-acetic acid 4(beta)-(3-methylbutanoic acid); Leucomycin V 3-acetic acid 4(β)-(3-methylbutanoic acid); Leucomycin V 3-acetic acid 4(b)-(3-methylbutanoic acid); Leucomycin V 3-acetic acid 4b-(3-methylbutanoic acid); Leucomycin V 3-acetate 4(beta)-(3-methylbutanoate); Leucomycin V 3-acetate 4(β)-(3-methylbutanoate); Leucomycin V 3-acetate 4(b)-(3-methylbutanoate); Leucomycin V, 3-acetate 4b-(3-methylbutanoate); Leucomycin V 3-acetate 4b-(3-methylbutanoate); Antibiotic yl-704 a3; Kitasamycin a3; Leucomycin a3; Turimycin a5; Josamycinum; Josamycine; Josamicina; DB-043741; Wilprafen; Josamycin; yl-704 a3; EN-141; JM; Josamycin



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Sukran Ozturk, Sulhiye Yildiz, Polat Dursun, Burcu Yener Ilce, Ozlem Kaymaz. Mycoplasma hominis profile in women: Culture, kit, molecular diagnosis, antimicrobial resistance, and treatment. Microbial pathogenesis. 2019 Oct; 135(?):103635. doi: 10.1016/j.micpath.2019.103635. [PMID: 31352064]
  • Katsuhiko Matsui, Kanta Tachioka, Kei Onodera, Reiko Ikeda. Topical Application of Josamycin Inhibits Development of Atopic Dermatitis-Like Skin Lesions in NC/Nga Mice. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2017; 20(?):38-47. doi: 10.18433/j3gw3d. [PMID: 28459659]
  • Biyang Deng, Yanhui Kang, Xianfeng Li, Qiumei Xu. Determination of josamycin in rat plasma by capillary electrophoresis coupled with post-column electrochemiluminescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Nov; 859(1):125-30. doi: 10.1016/j.jchromb.2007.09.014. [PMID: 17928277]
  • Fathalla Belal, Abdel-Rahman A Al-Majed, Kamal E E Ibrahim, Nasr Y Khalil. Anodic polarographic determination of josamycin in formulations and spiked human urine. Farmaco (Societa chimica italiana : 1989). 2004 Jul; 59(7):537-42. doi: 10.1016/j.farmac.2004.02.002. [PMID: 15231429]
  • Abdulrahman A Al-Majed, Fathalla Belal, Nasr Y Khalil, Kamal E E Ibrahim. Kinetic spectrophotometric determination of josamycin in formulations and spiked human plasma using 3-methylbenzothiazolin-2-one hydrazone/Fe+3 system. Journal of AOAC International. 2004 Mar; 87(2):352-9. doi: 10.1093/jaoac/87.2.352. [PMID: 15164827]
  • Elena Ortega, M Antonia Escobar, José Juan Gaforio, Ignacio Algarra, Gerardo Alvarez De Cienfuegos. Modification of phagocytosis and cytokine production in peritoneal and splenic murine cells by erythromycin A, azithromycin and josamycin. The Journal of antimicrobial chemotherapy. 2004 Feb; 53(2):367-70. doi: 10.1093/jac/dkh069. [PMID: 14729765]
  • F Belal, A Al-Majed, K E E Ibrahim, N Y Khalil. Voltammetric determination of josamycin (a macrolide antibiotic) in dosage forms and spiked human urine. Journal of pharmaceutical and biomedical analysis. 2002 Oct; 30(3):705-13. doi: 10.1016/s0731-7085(02)00358-8. [PMID: 12367696]
  • K Kasahara, A Nishikawa, F Furukawa, S Ikezaki, Z Tanakamaru, I-S Lee, T Imazawa, M Hirose. A chronic toxicity study of josamycin in F344 rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2002 Jul; 40(7):1017-22. doi: 10.1016/s0278-6915(02)00068-6. [PMID: 12065224]
  • S Yamamoto, K Asano, T Shimane, T Hisamitsu, H Suzaki. Enhancement of endogenous corticosterone levels by a macrolide antibiotic, roxithromycin in mice. Life sciences. 2001 Jul; 69(10):1115-21. doi: 10.1016/s0024-3205(01)01199-7. [PMID: 11508344]
  • I V Maev, A L Vertkin, E I Vovk, A A Masharova, S D Bezborodnyĭ, E G Lebedeva. [Josamycin combination with ranitidine in therapy of gastroduodenal ulcer: clinical efficiency]. Klinicheskaia meditsina. 2000; 78(3):46-50. doi: NULL. [PMID: 10790966]
  • K Kasahara, A Nishikawa, F Furukawa, S Ikezaki, Z Tanakamaru, H Takagi, T Ikeda, T Imazawa, M Takahashi. Suppressive effects of josamycin on the development of altered liver cell foci and chronic nephropathy in a carcinogenicity study. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1999 Jan; 37(1):61-7. doi: 10.1016/s0278-6915(98)00100-8. [PMID: 10069483]
  • Y Kikuchi, T Teramura, J Sekino, T Nishimura, H Miura, T Watanabe, S Higuchi. Sensitive and specific method for the determination of josamycin in human plasma by liquid chromatography-mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 1998 Dec; 720(1-2):81-7. doi: 10.1016/s0378-4347(98)00430-7. [PMID: 9892070]
  • M Skinner, I Kanfer. Comparative bioavailability of josamycin, a macrolide antibiotic, from a tablet and solution and the influence of dissolution on in vivo release. Biopharmaceutics & drug disposition. 1998 Jan; 19(1):21-9. doi: 10.1002/(sici)1099-081x(199801)19:1<21::aid-bdd69>3.0.co;2-g. [PMID: 9510982]
  • G C Li, C Y Chen, M Y Yang. [A comparative study on the pharmacokinetics of josamycin in Chinese Han, Uighur and Kazak healthy volunteers]. Yao xue xue bao = Acta pharmaceutica Sinica. 1997; 32(3):231-3. doi: NULL. [PMID: 11327029]
  • S W Borron, J M Scherrmann, F J Baud. Markedly altered colchicine kinetics in a fatal intoxication: examination of contributing factors. Human & experimental toxicology. 1996 Nov; 15(11):885-90. doi: 10.1177/096032719601501104. [PMID: 8938483]
  • E J Van Hoogdalem, I J Terpstra, W J Krauwinkel, N J Volkers-Kamermans, A L Baven, J S Verschoor. Multiple dose bioequivalence study with josamycin propionate, a drug with highly variable kinetics, in healthy volunteers. International journal of clinical pharmacology and therapeutics. 1996 May; 34(5):202-7. doi: NULL. [PMID: 8738856]
  • D Capone, C Aiello, G A Santoro, A Gentile, P Stanziale, R D'Alessandro, P Imperatore, V Basile. Drug interaction between cyclosporine and two antimicrobial agents, josamycin and rifampicin, in organ-transplanted patients. International journal of clinical pharmacology research. 1996; 16(2-3):73-6. doi: . [PMID: 9063759]
  • S Ikezaki, A Nishikawa, F Furukawa, T Imazawa, M Mitsui, T Enami, M Takahashi. [A 13-week subchronic toxicity study of josamycin in F344 rats]. Eisei Shikenjo hokoku. Bulletin of National Institute of Hygienic Sciences. 1995; ?(113):44-50. doi: NULL. [PMID: 8717227]
  • P Leroy, D Decolin, A Nicolas, P Archimbault. Determination of josamycin residues in porcine tissues using high-performance liquid chromatography with pre-column derivatization and spectrofluorimetric detection. The Analyst. 1994 Dec; 119(12):2743-7. doi: 10.1039/an9941902743. [PMID: 7879887]
  • K Tateda, Y Ishii, Y Hirakata, T Matsumoto, A Ohno, K Yamaguchi. Profiles of outer membrane proteins and lipopolysaccharide of Pseudomonas aeruginosa grown in the presence of sub-MICs of macrolide antibiotics and their relation to enhanced serum sensitivity. The Journal of antimicrobial chemotherapy. 1994 Dec; 34(6):931-42. doi: 10.1093/jac/34.6.931. [PMID: 7730236]
  • L Hbabi, C Roques, G Michel, A M Perruchet, H Benoist. In vitro stimulation of polymorphonuclear cell adhesion by ribomunyl and antibiotic + ribomunyl combinations: effects on CD18, CD35 and CD16 expression. International journal of immunopharmacology. 1993 Feb; 15(2):163-73. doi: 10.1016/0192-0561(93)90092-d. [PMID: 8096833]
  • J V Torregrosa, J M Campistol, A Franco, J Andreu. Interaction of josamycin with cyclosporin A. Nephron. 1993; 65(3):476-7. doi: 10.1159/000187537. [PMID: 8290006]
  • P Dellamonica, R Garraffo, H Etesse-Carsenti, E Bernard, V Mondain. Pharmacokinetic and bacteriological study of cefadroxil-salicylate and josamycin-salicylate drug regimens. International journal of clinical pharmacology research. 1993; 13(1):11-20. doi: NULL. [PMID: 8509232]
  • Y Akimoto, Y Mochizuki, A Uda, H Omata, S Saito, K Kaneko, A Fujii, H Yamamoto. Josamycin concentrations in radicular cysts following a single oral administration. General pharmacology. 1993 Jan; 24(1):143-5. doi: 10.1016/0306-3623(93)90025-s. [PMID: 8482488]
  • M G el-Sayed, M I Abd el-Aziz, A M Abd el-Azem. Blood and tissue concentrations of trimethoprim following its administration alone and in combination with josamycin. DTW. Deutsche tierarztliche Wochenschrift. 1992 Apr; 99(4):154-6. doi: NULL. [PMID: 1606899]
  • M Tod, O Biarez, P Nicolas, O Petitjean. Sensitive determination of josamycin and rokitamycin in plasma by high-performance liquid chromatography with fluorescence detection. Journal of chromatography. 1992 Mar; 575(1):171-6. doi: 10.1016/0378-4347(92)80521-q. [PMID: 1517296]
  • M G el-Sayed, M I Abd el-Aziz, A M Abd el-Azem. Pharmacokinetics and tissue residues of josamycin in fowls. DTW. Deutsche tierarztliche Wochenschrift. 1992 Mar; 99(3):113-6. doi: NULL. [PMID: 1576948]
  • T Watanabe, M Kanno, E Tejima, Y Orikasa. Effects of macrolides on ultrastructure of Staphylococcus aureus during postantibiotic phase. Drugs under experimental and clinical research. 1992; 18(3):81-8. doi: . [PMID: 1425207]
  • J S Brazier, D M Citron, E J Goldstein. A selective medium for Fusobacterium spp. The Journal of applied bacteriology. 1991 Oct; 71(4):343-6. doi: 10.1111/j.1365-2672.1991.tb03798.x. [PMID: 1960109]
  • H Cannell, C Kerawala, A M Sefton, J P Maskell, A Seymour, Z M Sun, J D Williams. Failure of two macrolide antibiotics to prevent post-extraction bacteraemia. British dental journal. 1991 Sep; 171(6):170-3. doi: 10.1038/sj.bdj.4807639. [PMID: 1832916]
  • B Uzzan, P Nicolas, G Perret, R Vassy, M Tod, O Petitjean. Effects of troleandomycin and josamycin on thyroid hormone and steroid serum levels, liver function tests and microsomal monooxygenases in healthy volunteers: a double blind placebo-controlled study. Fundamental & clinical pharmacology. 1991; 5(6):513-26. doi: 10.1111/j.1472-8206.1991.tb00738.x. [PMID: 1955196]
  • A M Sefton, J P Maskell, C Kerawala, H Cannell, A Seymour, Z M Sun, J D Williams. Comparative efficacy and tolerance of erythromycin and josamycin in the prevention of bacteraemia following dental extraction. The Journal of antimicrobial chemotherapy. 1990 Jun; 25(6):975-84. doi: 10.1093/jac/25.6.975. [PMID: 2196261]
  • S Morimoto, T Nagate, K Sugita, T Ono, K Numata, J Miyachi, Y Misawa, K Yamada, S Omura. Chemical modification of erythromycins. III. In vitro and in vivo antibacterial activities of new semisynthetic 6-O-methylerythromycins A, TE-031 (clarithromycin) and TE-032. The Journal of antibiotics. 1990 Mar; 43(3):295-305. doi: 10.7164/antibiotics.43.295. [PMID: 2139023]
  • M T Labro, C Babin-Chevaye. Synergistic interaction of josamycin with human neutrophils bactericidal function in vitro. The Journal of antimicrobial chemotherapy. 1989 Nov; 24(5):731-40. doi: 10.1093/jac/24.5.731. [PMID: 2557317]
  • S Kohno, H Koga, K Yamaguchi, M Masaki, Y Inoue, Y Dotsu, Y Masuyama, T Hayashi, M Hirota, A Saito. A new macrolide, TE-031 (A-56268), in treatment of experimental Legionnaires' disease. The Journal of antimicrobial chemotherapy. 1989 Sep; 24(3):397-405. doi: 10.1093/jac/24.3.397. [PMID: 2530201]
  • A Uda, H Omata, J Shibutani, H Nishimura, M Komiya, Y Akimoto, K Kaneko, A Fujii. Josamycin concentrations in human dental granuloma after a single oral administration of josamycin. General pharmacology. 1989; 20(6):823-5. doi: 10.1016/0306-3623(89)90337-6. [PMID: 2591712]
  • M Ducci, V Scalori. A rapid and sensitive high-pressure liquid chromatographic method for monitoring josamycin levels in plasma. International journal of clinical pharmacology research. 1984; 4(3):195-9. doi: NULL. [PMID: 6490238]
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