Dirithromycin (BioDeep_00000597294)
代谢物信息卡片
化学式: C42H78N2O14 (834.5453)
中文名称: 地红霉素
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCC1C(C2C(C(C(CC(C(C(C(C(C(=O)O1)C)OC3CC(C(C(O3)C)O)(C)OC)C)OC4C(C(CC(O4)C)N(C)C)O)(C)O)C)NC(O2)COCCOC)C)(C)O
InChI: InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1
描述信息
The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms.
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
同义名列表
1 个代谢物同义名
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:474014
- KEGGdrug: D03865
- PubChem: 6473883
- Metlin: METLIN3988
- DrugBank: DB00954
- ChEMBL: CHEMBL1237072
- ChEMBL: CHEMBL3039471
- CAS: 62013-04-1
- MetaboLights: MTBLC474014
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)
0 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。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- Kadri Adel, Mosbah Amor, Redissi Alaeddine, Noumi Emira, Alreshidi Mousa, Aouadi Kaïss, Ghannay Siwar, Siddiqui Arif Jamal, Adnan Mohd, Vincenzo De Feo, Snoussi Mejdi. Comparative Computational Analysis of Dirithromycin and Azithromycin in Search for a Potent Drug against COVID-19 caused by SARS-CoV-2: Evidence from molecular docking and dynamic simulation.
Cellular and molecular biology (Noisy-le-Grand, France).
2022 Feb; 67(5):371-386. doi:
10.14715/cmb/2021.67.5.50. [PMID: 35818230] - Hua-Lin Cai, Feng Wang, Huan-De Li, Wen-Xing Peng, Rong-Hua Zhu, Yang Deng, Pei Jiang, Miao Yan, Si-Miao Hu, Su-Yun Lei, Chang Chen. Quantitative analysis of erythromycylamine in human plasma by liquid chromatography-tandem mass spectrometry and its application in a bioequivalence study of dirithromycin enteric-coated tablets with a special focus on the fragmentation pattern and carryover effect.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2014 Feb; 947-948(?):156-63. doi:
10.1016/j.jchromb.2013.12.019. [PMID: 24424301] - Yun-Qing Liu, Qi-Yuan Chen, Ben-Mei Chen, Shao-Gang Liu, Fu-Liang Deng, Ping Zhou. Quantitative determination of erythromycylamine in human plasma by liquid chromatography-mass spectrometry and its application in a bioequivalence study of dirithromycin.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Mar; 864(1-2):1-8. doi:
10.1016/j.jchromb.2007.12.021. [PMID: 18296129] - T Mazzei, C Surrenti, A Novelli, M R Biagini, S Fallani, M I Cassetta, S Conti, E Surrenti. Pharmacokinetics of dirithromycin in patients with mild or moderate cirrhosis.
Antimicrobial agents and chemotherapy.
1999 Jul; 43(7):1556-9. doi:
10.1128/aac.43.7.1556. [PMID: 10390202] - S A McConnell, A N Nafziger, G W Amsden. Lack of effect of dirithromycin on theophylline pharmacokinetics in healthy volunteers.
The Journal of antimicrobial chemotherapy.
1999 May; 43(5):733-6. doi:
10.1093/jac/43.5.733. [PMID: 10382900] - V S Watkins, R E Polk, J L Stotka. Drug interactions of macrolides: emphasis on dirithromycin.
The Annals of pharmacotherapy.
1997 Mar; 31(3):349-56. doi:
10.1177/106002809703100314. [PMID: 9066944] - K Bachmann, T J Sullivan, J H Reese, L Jauregui, K Miller, M Scott, J Stotka, J Harris. A study of the interaction between dirithromycin and astemizole in healthy adults.
American journal of therapeutics.
1997 Feb; 4(2-3):73-9. doi:
10.1097/00045391-199702000-00004. [PMID: 10423595] - H F Geerdes-Fenge, B Goetschi, M Rau, K Borner, P Koeppe, K Wettich, H Lode. Comparative pharmacokinetics of dirithromycin and erythromycin in normal volunteers with special regard to accumulation in polymorphonuclear leukocytes and in saliva.
European journal of clinical pharmacology.
1997; 53(2):127-33. doi:
10.1007/s002280050350. [PMID: 9403284] - I Moutard, B Gressier, C Brunet, T Dine, M Luyckx, M Cazin, J C Cazin. In vitro interaction between dirithromycin or its metabolite, erythromycylamine, and oxidative polymorphonuclear metabolism.
The Journal of antibiotics.
1997 Jan; 50(1):53-7. doi:
10.7164/antibiotics.50.53. [PMID: 9066766] - M G Matera, M A Tufano, M Polverino, F Rossi, M Cazzola. Pulmonary concentrations of dirithromycin and erythromycin during acute exacerbation of mild chronic obstructive pulmonary disease.
The European respiratory journal.
1997 Jan; 10(1):98-103. doi:
10.1183/09031936.97.10010098. [PMID: 9032500] - M Müller, O Haag, T Burgdorff, A Georgopoulos, W Weninger, B Jansen, G Stanek, H Pehamberger, E Agneter, H G Eichler. Characterization of peripheral-compartment kinetics of antibiotics by in vivo microdialysis in humans.
Antimicrobial agents and chemotherapy.
1996 Dec; 40(12):2703-9. doi:
10.1128/aac.40.12.2703. [PMID: 9124826] - J M Hernández, G D Sides, P M Conforti, M G Smietana. Clinical efficacy of dirithromycin in patients with bacteremic pneumonia.
Clinical therapeutics.
1996 Nov; 18(6):1128-38. doi:
10.1016/s0149-2918(96)80067-1. [PMID: 9001829] - J M Benson, J Arnold, S C Manning, D L Coleman, G D Sides, P M Conforti, E Lemon, V S Watkins. Tonsillar tissue penetration of dirithromycin after multiple doses.
Journal of clinical pharmacology.
1996 Sep; 36(9):832-7. doi:
10.1002/j.1552-4604.1996.tb04257.x. [PMID: 8889904] - I Shinkai, Y Ohta. New drugs--reports of new drugs recently approved by the FDA. Dirithromycin.
Bioorganic & medicinal chemistry.
1996 Apr; 4(4):521-2. doi:
10.1016/0968-0896(96)00052-1. [PMID: 8735838] - D P Wermeling, M H Chandler, G D Sides, D Collins, K N Muse. Dirithromycin increases ethinyl estradiol clearance without allowing ovulation.
Obstetrics and gynecology.
1995 Jul; 86(1):78-84. doi:
10.1016/0029-7844(95)00075-3. [PMID: 7784027] - A Philippon, R Cluzel, C J Soussy. [Azithromycin: critical points].
Pathologie-biologie.
1995 Jun; 43(6):488-97. doi:
NULL. [PMID: 8539070] - M Cazzola, M G Matera, M A Tufano, M Polverino, P Catalanotti, L Varanese, F Rossi. Pulmonary penetration of dirithromycin in patients suffering from acute exacerbation of chronic bronchitis.
Pulmonary pharmacology.
1994 Dec; 7(6):377-81. doi:
10.1006/pulp.1994.1044. [PMID: 7549225] - D LaBreque, F Johlin, R Janda, T Shreves, D Gereats, K DeSante, B Cerimele, T Lanier, G Sides. Pharmacokinetics of dirithromycin in patients with impaired hepatic function.
The Journal of antimicrobial chemotherapy.
1993 Nov; 32(5):741-50. doi:
10.1093/jac/32.5.741. [PMID: 8125838] - K Bachmann, L Jauregui, G Sides, T J Sullivan. Steady-state pharmacokinetics of theophylline in COPD patients treated with dirithromycin.
Journal of clinical pharmacology.
1993 Sep; 33(9):861-5. doi:
10.1002/j.1552-4604.1993.tb01964.x. [PMID: 8227485] - G D Sides, B J Cerimele, H R Black, U Busch, K A DeSante. Pharmacokinetics of dirithromycin.
The Journal of antimicrobial chemotherapy.
1993 Mar; 31 Suppl C(?):65-75. doi:
10.1093/jac/31.suppl_c.65. [PMID: 8478313] - L Varanese. Pharmacokinetics and safety of dirithromycin in the elderly.
The Journal of antimicrobial chemotherapy.
1993 Mar; 31 Suppl C(?):169-74. doi:
10.1093/jac/31.suppl_c.169. [PMID: 8478308] - A L Barry, M A Pfaller, P C Fuchs. Dirithromycin disc susceptibility tests: interpretative criteria and quality control parameters.
The Journal of antimicrobial chemotherapy.
1993 Mar; 31 Suppl C(?):27-37. doi:
10.1093/jac/31.suppl_c.27. [PMID: 8478310] - E Bergogne-Bérézin. Tissue distribution of dirithromycin: comparison with erythromycin.
The Journal of antimicrobial chemotherapy.
1993 Mar; 31 Suppl C(?):77-87. doi:
10.1093/jac/31.suppl_c.77. [PMID: 8478314] - S A Eckernäs, A Grahnén, C E Nord. Impact of dirithromycin on the normal oral and intestinal microflora.
European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology.
1991 Aug; 10(8):688-92. doi:
10.1007/bf01975827. [PMID: 1748127] - F T Counter, P W Ensminger, D A Preston, C Y Wu, J M Greene, A M Felty-Duckworth, J W Paschal, H A Kirst. Synthesis and antimicrobial evaluation of dirithromycin (AS-E 136; LY237216), a new macrolide antibiotic derived from erythromycin.
Antimicrobial agents and chemotherapy.
1991 Jun; 35(6):1116-26. doi:
10.1128/aac.35.6.1116. [PMID: 1929252] - K Bachmann, M Nunlee, M Martin, T Sullivan, L Jauregui, K DeSante, G D Sides. Changes in the steady-state pharmacokinetics of theophylline during treatment with dirithromycin.
Journal of clinical pharmacology.
1990 Nov; 30(11):1001-5. doi:
10.1002/j.1552-4604.1990.tb03586.x. [PMID: 2243147] - K W Yu, H C Neu. In vitro activity of dirithromycin (LY 237216) compared with activities of other macrolide antibiotics.
Antimicrobial agents and chemotherapy.
1990 Sep; 34(9):1839-42. doi:
10.1128/aac.34.9.1839. [PMID: 2126695]
