Loracarbef (BioDeep_00000033235)

   

human metabolite blood metabolite Chemicals and Drugs Antibiotics


代谢物信息卡片


(6R,7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

化学式: C16H16ClN3O4 (349.0829286)
中文名称: 氯碳头孢
谱图信息: 最多检出来源 Homo sapiens(blood) 76.47%

分子结构信息

SMILES: C1CC(=C(N2C1C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)Cl
InChI: InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12+/m1/s1

描述信息

Loracarbef is only found in individuals that have used or taken this drug. It is a carbacephem antibiotic sometimes grouped together with the second-generation cephalosporin antibiotics. It is marketed under the trade name Lorabid.Loracarbef is an oral, synthetic beta-lactam antibiotic of the carbacephem class. Chemically, carbacephems differ from cephalosporin-class antibiotics in the dihydrothiazine ring where a methylene group has been substituted for a sulfur atom. Loracarbef has a spectrum of activity similar to that of the second generation cephalosporins. It is structurally identical to cefaclor except for a sulfur atom that has been replaced by a methylene group. This change gives greater chemical stability in solution and allows storage at room temperature. Loracarbef, like all b-lactams and cephalosporins, inhibits penicillin binding proteins, enzymes that create the cross-linkage of the peptidoglycan polymer. This binding leads to interference with the formation and remodeling of the cell wall structure.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01D - Other beta-lactam antibacterials > J01DC - Second-generation cephalosporins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D002511 - Cephalosporins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams
C254 - Anti-Infective Agent > C258 - Antibiotic > C260 - Beta-Lactam Antibiotic

同义名列表

14 个代谢物同义名

(6R,7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Monarch brand OF loracarbef monohydrate; Syntex brand OF loracarbef monohydrate; Zambon brand OF loracarbef monohydrate; Lilly brand OF loracarbef monohydrate; Lilly brand OF loracarbef; Loracarbef monohydrate; Loracarbefum; loracarbef; LORACABEF; Lorafem; Lorabid; Carbac; Lorax



数据库引用编号

8 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

  • Min Guan, Qiao-Ling Zhu, Yang Liu, Yong-Yan Bei, Zong-Lin Gu, Xue-Nong Zhang, Qiang Zhang. Uptake and transport of a novel anticancer drug-delivery system: lactosyl-norcantharidin-associated N-trimethyl chitosan nanoparticles across intestinal Caco-2 cell monolayers. International journal of nanomedicine. 2012; 7(?):1921-30. doi: 10.2147/ijn.s30034. [PMID: 22605938]
  • A T Bapujee, T Singh, T Ahmed, T Monif, N Saha, P L Sharma. The effect of four different types of diet on the bioavailability of loracarbef. European journal of drug metabolism and pharmacokinetics. 2007 Oct; 32(4):205-11. doi: 10.1007/bf03191005. [PMID: 18348469]
  • Arne Orrling, Carl Kamme, Anna Stjernquist-Desatnik. Penicillin V, loracarbef and clindamycin in tonsillar surface fluid during acute group A streptococcal pharyngotonsillitis. Scandinavian journal of infectious diseases. 2005; 37(6-7):429-35. doi: 10.1080/00365540410020947. [PMID: 16012002]
  • O S Aljitawi, K Krishnan, B R Curtis, D W Bougie, R H Aster. Serologically documented loracarbef (Lorabid)-induced immune thrombocytopenia. American journal of hematology. 2003 May; 73(1):41-3. doi: 10.1002/ajh.10307. [PMID: 12701119]
  • R Bennet, M Eriksson, C E Nord. The fecal microflora of 1-3-month-old infants during treatment with eight oral antibiotics. Infection. 2002 Jun; 30(3):158-60. doi: 10.1007/s15010-002-2140-z. [PMID: 12120942]
  • F Vogel, H R Ochs, K Wettich, S Kalich, I Nilsson-Ehle, I Odenholt, C E Nord. Effect of step-down therapy of ceftriaxone plus loracarbef versus parenteral therapy of ceftriaxone on the intestinal microflora in patients with community-acquired pneumonia. Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases. 2001 Jul; 7(7):376-9. doi: 10.1046/j.1198-743x.2001.00264.x. [PMID: 11531985]
  • G E Stein, S Schooley, R D Walker, L Strenkoski-Nix. Pharmacodynamic activity of five oral cephalosporins against Haemophilus influenzae. Pharmacotherapy. 1997 Mar; 17(2):235-41. doi: NULL. [PMID: 9085313]
  • M Stenquist, L Olen, M Jannert, L Näslund, M L Zeckel. Penetration of loracarbef into the maxillary sinus: a pharmacokinetic assessment. Clinical therapeutics. 1996 Mar; 18(2):273-84. doi: 10.1016/s0149-2918(96)80008-7. [PMID: 8733988]
  • B M Tune, C Y Hsu, D Fravert. Cephalosporin and carbacephem nephrotoxicity. Roles of tubular cell uptake and acylating potential. Biochemical pharmacology. 1996 Feb; 51(4):557-61. doi: 10.1016/0006-2952(95)02237-6. [PMID: 8619902]
  • M Boll, M Herget, M Wagener, W M Weber, D Markovich, J Biber, W Clauss, H Murer, H Daniel. Expression cloning and functional characterization of the kidney cortex high-affinity proton-coupled peptide transporter. Proceedings of the National Academy of Sciences of the United States of America. 1996 Jan; 93(1):284-9. doi: 10.1073/pnas.93.1.284. [PMID: 8552623]
  • R E Thieme, S A Caldwell, G M Lum. Acute interstitial nephritis associated with loracarbef therapy. The Journal of pediatrics. 1995 Dec; 127(6):997-1000. doi: 10.1016/s0022-3476(95)70048-x. [PMID: 8523206]
  • C Connell, S Aspinall, J Corkill. Sputum and serum pharmacokinetics of loracarbef (LY163892) in patients with bronchial sepsis. The Journal of antimicrobial chemotherapy. 1995 Aug; 36(2):446-7. doi: 10.1093/jac/36.2.446. [PMID: 8522479]
  • D S Sitar, D J Hoban, F Y Aoki. Pharmacokinetic disposition of loracarbef in healthy young men and women at steady state. Journal of clinical pharmacology. 1994 Sep; 34(9):924-9. doi: 10.1002/j.1552-4604.1994.tb04006.x. [PMID: 7983236]
  • S L Hill, D Bilton, M M Johnson, A Pye, J L Mitchell, R A Stockley. Sputum and serum pharmacokinetics of loracarbef (LY163892) in patients with chronic bronchial sepsis. The Journal of antimicrobial chemotherapy. 1994 Jan; 33(1):129-36. doi: 10.1093/jac/33.1.129. [PMID: 8157553]
  • A S Lees, J M Andrews, R Wise. The pharmacokinetics, tissue penetration and in-vitro activity of loracarbef, a beta-lactam antibiotic of the carbacephem class. The Journal of antimicrobial chemotherapy. 1993 Dec; 32(6):853-9. doi: 10.1093/jac/32.6.853. [PMID: 8144425]
  • D G Therasse, D S Farlow, R L Davidson, L J Quadracci, B L Hatcher, B J Cerimele, K A DeSante. Effects of renal dysfunction on the pharmacokinetics of loracarbef. Clinical pharmacology and therapeutics. 1993 Sep; 54(3):311-6. doi: 10.1038/clpt.1993.152. [PMID: 8375126]
  • R N Brogden, D McTavish. Loracarbef. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1993 May; 45(5):716-36. doi: 10.2165/00003495-199345050-00008. [PMID: 7686466]
  • R W Force, M C Nahata. Loracarbef: a new orally administered carbacephem antibiotic. The Annals of pharmacotherapy. 1993 Mar; 27(3):321-9. doi: 10.1177/106002809302700315. [PMID: 8453172]
  • T Shetler, A Bendele, M Buening, J Clemens, W Colbert, A Deldar, D Helton, J McGrath, H Shannon, J Turk. General pharmacology of loracarbef in animals. Arzneimittel-Forschung. 1993 Jan; 43(1):60-70. doi: NULL. [PMID: 8447851]
  • S Roller, H Lode, I Stelzer, K M Deppermann, M Boeckh, P Koeppe. Pharmacokinetics of loracarbef and interaction with acetylcysteine. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology. 1992 Sep; 11(9):851-5. doi: 10.1007/bf01960891. [PMID: 1468429]
  • M C Nahata, K I Koranyi. Pharmacokinetics of loracarbef in pediatric patients. European journal of drug metabolism and pharmacokinetics. 1992 Jul; 17(3):201-4. doi: 10.1007/bf03190146. [PMID: 1490489]
  • K A DeSante, M L Zeckel. Pharmacokinetic profile of loracarbef. The American journal of medicine. 1992 Jun; 92(6A):16S-19S. doi: 10.1016/0002-9343(92)90602-8. [PMID: 1621740]
  • P Van der Auwera. Bactericidal titers of loracarbef (LY 163892) in serum and killing rates in volunteers receiving 400 versus 200 milligrams. Antimicrobial agents and chemotherapy. 1992 Mar; 36(3):521-6. doi: 10.1128/aac.36.3.521. [PMID: 1622160]
  • P M Kovach, R J Lantz, G Brier. High-performance liquid chromatographic determination of loracarbef, a potential metabolite, cefaclor and cephalexin in human plasma, serum and urine. Journal of chromatography. 1991 Jun; 567(1):129-39. doi: 10.1016/0378-4347(91)80317-6. [PMID: 1918240]
  • A G Arguedas, A C Arrieta, H R Stutman, J C Akaniro, M I Marks. In-vitro activity of cefprozil (BMY 28100) and loracarbef (LY 163892) against pathogens obtained from middle ear fluid. The Journal of antimicrobial chemotherapy. 1991 Mar; 27(3):311-8. doi: 10.1093/jac/27.3.311. [PMID: 1903788]
  • C E Nord, A Grahnen, S A Eckernäs. Effect of loracarbef on the normal oropharyngeal and intestinal microflora. Scandinavian journal of infectious diseases. 1991; 23(2):255-60. doi: 10.3109/00365549109023409. [PMID: 1853174]
  • H Kusmiesz, S Shelton, O Brown, S Manning, J D Nelson. Loracarbef concentrations in middle ear fluid. Antimicrobial agents and chemotherapy. 1990 Oct; 34(10):2030-1. doi: 10.1128/aac.34.10.2030. [PMID: 2291672]
  • M F Tripodi, L E Adinolfi, R Utili, A Marrone, G Ruggiero. Influence of subinhibitory concentrations of loracarbef (LY 163892) and daptomycin (LY 146032) on bacterial phagocytosis, killing and serum sensitivity. The Journal of antimicrobial chemotherapy. 1990 Oct; 26(4):491-501. doi: 10.1093/jac/26.4.491. [PMID: 2174852]
  • J D Nelson, S Shelton, H Kusmiesz. Pharmacokinetics of LY163892 in infants and children. Antimicrobial agents and chemotherapy. 1988 Nov; 32(11):1738-9. doi: 10.1128/aac.32.11.1738. [PMID: 3252754]
  • J H Jorgensen, J S Redding, L A Maher. Influence of storage and susceptibility test conditions on stability and activity of LY163892 and four other cephalosporins. Antimicrobial agents and chemotherapy. 1988 Oct; 32(10):1477-80. doi: 10.1128/aac.32.10.1477. [PMID: 3190179]