Cyclacillin (BioDeep_00000009383)

 

Secondary id: BioDeep_00001871401

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

化学式: C15H23N3O4S (341.1409198)
中文名称: 环己西林
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
InChI: InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1

描述信息

Cyclacillin is only found in individuals that have used or taken this drug. It is a cyclohexylamido analog of penicillanic acid. [PubChem]The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D010406 - Penicillins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams
C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic
Same as: D01334

同义名列表

28 个代谢物同义名

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-; (2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; (2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(1-Aminocyclohexanecarboxamido)penicillanic acid; 6-(1-Aminocyclohexylcarboxamido)penicillanic acid; 6-(1-Aminocyclohexanecarboxamido)penicillanate; 6-(1-Aminocyclohexylcarboxamido)penicillanate; (1-Aminocyclohexyl)penicillin; Aminocyclohexylpenicillin; Ciclacillinum; Ciclacilline; MLS002694856; Ciclacilina; Syngacillin; Ciclacillin; Ciclacillum; Ultracillin; Cyclacillin; Bastcillin; Cyclapen-W; Vastcillin; Citosarin; Cyclapen; Calthor; Wyvital; Vipicil; ACPC



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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INOH(0)

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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

  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Ivan Sabolić, Abdul R Asif, Wolfgang E Budach, Christoph Wanke, Andrew Bahn, Gerhard Burckhardt. Gender differences in kidney function. Pflugers Archiv : European journal of physiology. 2007 Dec; 455(3):397-429. doi: 10.1007/s00424-007-0308-1. [PMID: 17638010]
  • Hua Lin, Nicola King. Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes. Pflugers Archiv : European journal of physiology. 2007 Mar; 453(6):915-22. doi: 10.1007/s00424-006-0171-5. [PMID: 17120020]
  • Petra Luckner, Matthias Brandsch. Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2005 Jan; 59(1):17-24. doi: 10.1016/j.ejpb.2004.07.008. [PMID: 15567297]
  • M E Ganapathy, W Huang, D P Rajan, A L Carter, M Sugawara, K Iseki, F H Leibach, V Ganapathy. beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. The Journal of biological chemistry. 2000 Jan; 275(3):1699-707. doi: 10.1074/jbc.275.3.1699. [PMID: 10636865]
  • T Terada, H Saito, M Mukai, K Inui. Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. The American journal of physiology. 1997 11; 273(5):F706-11. doi: 10.1152/ajprenal.1997.273.5.f706. [PMID: 9374833]
  • M E Ganapathy, M Brandsch, P D Prasad, V Ganapathy, F H Leibach. Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. The Journal of biological chemistry. 1995 Oct; 270(43):25672-7. doi: 10.1074/jbc.270.43.25672. [PMID: 7592745]
  • W M Scheld, A Sydnor, B Farr, J C Gratz, J M Gwaltney. Comparison of cyclacillin and amoxicillin for therapy for acute maxillary sinusitis. Antimicrobial agents and chemotherapy. 1986 Sep; 30(3):350-3. doi: 10.1128/aac.30.3.350. [PMID: 3535660]
  • M Bone, J Symonds, P Dougan. Penetration of ciclacillin into bronchial secretions. Chemioterapia : international journal of the Mediterranean Society of Chemotherapy. 1986 Apr; 5(2):105-8. doi: NULL. [PMID: 3708715]
  • J Haginaka, J Wakai. High-performance liquid chromatographic assay of ampicillin, amoxicillin and ciclacillin in serum and urine using a pre-column reaction with 1,2,4-triazole and mercury(II) chloride. The Analyst. 1985 Nov; 110(11):1277-81. doi: 10.1039/an9851001277. [PMID: 4083501]
  • J Sjövall, G Alván, D Westerlund. Oral cyclacillin interacts with the absorption of oral ampicillin, amoxycillin, and bacampicillin. European journal of clinical pharmacology. 1985; 29(4):495-502. doi: 10.1007/bf00613468. [PMID: 3912193]
  • C M Ginsburg, G H McCracken, T C Zweighaft, J C Clahsen. Comparative pharmacokinetics of cyclacillin and amoxicillin in infants and children. Antimicrobial agents and chemotherapy. 1981 Jun; 19(6):1086-8. doi: 10.1128/aac.19.6.1086. [PMID: 7271275]
  • H Aratani, H Tateishi, S Negita. [Studies on the distributions of antibiotics in the oral tissues: Experimental staphylococcal infection in rats, and effect of serratiopeptidase on the distributions of antibiotics (author's transl)]. The Japanese journal of antibiotics. 1980 May; 33(5):623-35. doi: . [PMID: 7001087]
  • R W Schaedler, G H Warren. Effect of cyclacillin and ampicillin on the gut flora of mice. Chemotherapy. 1980; 26(4):289-96. doi: 10.1159/000237919. [PMID: 7389426]
  • E Tiesler, H Ronald. [Serum and tissue levels of ciclacillin]. Zeitschrift fur Orthopadie und ihre Grenzgebiete. 1980; 118(3):320-3. doi: 10.1055/s-2008-1053512. [PMID: 6774497]
  • K F Wagner, A D Blair, G W Counts, K K Holmes. Pharmacological and in vitro evaluation of cyclacillin: assessment as potential single-dose therapy for treatment of Neisseria gonorrhoeae infection. Antimicrobial agents and chemotherapy. 1980 Jan; 17(1):89-91. doi: 10.1128/aac.17.1.89. [PMID: 6766294]
  • K Matsumoto. [Clinical studies on serum and intra-tonsillar concentrations of ciclacillin (Vasticillin 'Takeda') and ampicillin (Solcillin 'Takeda') (author's transl)]. The Japanese journal of antibiotics. 1979 Nov; 32(11):1196-202. doi: NULL. [PMID: 513302]
  • H J Dengler, M Eichelbaum. [Polymorphisms and deficient drug metabolism as triggers of toxic reactions (author's transl)]. Arzneimittel-Forschung. 1977; 27(96):1836-44. doi: NULL. [PMID: 579150]
  • G H Warren. Cyclacillin: microbiological and pharmacological properties and use in chemotherapy of infection - a critical appraisal. Chemotherapy. 1976; 22(3-4):154-82. doi: 10.1159/000221924. [PMID: 773605]
  • P Arend, H Sous, G Poszich, H Mŭckter. Relationship between the chemotherapeutic effectiveness of ciclacillin and ampicillin and the time of their administration in experimental infections. Arzneimittel-Forschung. 1975 Sep; 25(9):1382-5. doi: . [PMID: 1103895]
  • H W Ruelius. Interaction of drug metabolism with the other elements of drug safety evaluation. Drug metabolism reviews. 1975; 4(1):115-33. doi: 10.3109/03602537508993751. [PMID: 812688]
  • F W Janssen, E M Young, S K Kirkman, H P Agersborg, W E Tucker, H W Ruelius. Metabolic and pathologic investigation of 1-aminocyclohexanecarboxylic acid (ACHC), a metabolite of 6-(1-aminocyclohexanecarboxamido)-penicillanic acid (cyclacillin). Toxicology and applied pharmacology. 1974 Jul; 29(1):19-34. doi: 10.1016/0041-008x(74)90158-6. [PMID: 4378191]
  • W E Tucker, F W Janssen, H P Agersborg, E M Young, H W Ruelius. Sex- and species-related nephropathy of 6-(1-aminocyclohexanecarboxamido)penicillanic acid (cyclacillin) and its relationship to the metabolic disposition of the drug. Toxicology and applied pharmacology. 1974 Jul; 29(1):1-18. doi: 10.1016/0041-008x(74)90157-4. [PMID: 4283678]