Ceftibuten (BioDeep_00000006665)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

化学式: C15H14N4O6S2 (410.0354744)
中文名称: 头孢布烯
谱图信息: 最多检出来源 Homo sapiens(blood) 21.95%

分子结构信息

SMILES: C(=C(\c1csc(N)n1)/C(=O)N[C@@H]1C(=O)N2C(=CCS[C@H]12)C(=O)O)/CC(=O)O
InChI: InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1

描述信息

Ceftibuten is only found in individuals that have used or taken this drug. It is a third-generation cephalosporin antibiotic. It is an orally-administered agent. Cefalexin is used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01D - Other beta-lactam antibacterials > J01DD - Third-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

17 个代谢物同义名

(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (+)-(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; (+)-(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate; 7-(2-(2-Amino-4-thiazolyl)-4-carboxy-2-butenoylamino)-3-cephem-4-carboxylic acid; ceftibuten (stereochemistry not defined); cis-Ceftibuten; Ceftibutenum; Ceftibuteno; Ceftibutene; Ceftibuten; Cedex; Cedax; CETB; Ceftibuten

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:3510
KEGG: C08117
KEGGdrug: D00922
PubChem: 5282242
PubChem: 2654
HMDB: HMDB0015485
Metlin: METLIN44425
DrugBank: DB01415
ChEMBL: CHEMBL1605
Wikipedia: Ceftibuten
MeSH: Ceftibuten
chemspider: 4445419
CAS: 97519-39-6
PMhub: MS000019743
PubChem: 10317
NIKKAJI: J227.557K
RefMet: Ceftibuten
KNApSAcK: 3510

分类词条

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

9606 - Homo sapiens: -

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

Kamilia Abdelraouf, Sean M Stainton, David P Nicolau. In Vivo Pharmacodynamic Profile of Ceftibuten-Clavulanate Combination against Extended-Spectrum-β-Lactamase-Producing Enterobacteriaceae in the Murine Thigh Infection Model. Antimicrobial agents and chemotherapy. 2019 07; 63(7):. doi: 10.1128/aac.00145-19. [PMID: 31061165]
Aaron M Teitelbaum, Anja Meissner, Ryan A Harding, Christopher A Wong, Courtney C Aldrich, Rory P Remmel. Synthesis, pH-dependent, and plasma stability of meropenem prodrugs for potential use against drug-resistant tuberculosis. Bioorganic & medicinal chemistry. 2013 Sep; 21(17):5605-17. doi: 10.1016/j.bmc.2013.05.024. [PMID: 23845282]
Thomas J Neuhaus, Christoph Berger, Katja Buechner, Paloma Parvex, Gian Bischoff, Philippe Goetschel, Daniela Husarik, Ulrich Willi, Luciano Molinari, Christoph Rudin, Alain Gervaix, Urs Hunziker, Sergio Stocker, Eric Girardin, David Nadal. Randomised trial of oral versus sequential intravenous/oral cephalosporins in children with pyelonephritis. European journal of pediatrics. 2008 Sep; 167(9):1037-47. doi: 10.1007/s00431-007-0638-1. [PMID: 18074149]
Miyako Okamura, Tomohiro Terada, Toshiya Katsura, Ken-Ichi Inui. Inhibitory effect of zinc on the absorption of beta-lactam antibiotic ceftibuten via the peptide transporters in rats. Drug metabolism and pharmacokinetics. 2008; 23(6):464-8. doi: 10.2133/dmpk.23.464. [PMID: 19122341]
Annegret Biegel, Sabine Gebauer, Bianka Hartrodt, Ilka Knütter, Klaus Neubert, Matthias Brandsch, Iris Thondorf. Recognition of 2-aminothiazole-4-acetic acid derivatives by the peptide transporters PEPT1 and PEPT2. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2007 Sep; 32(1):69-76. doi: 10.1016/j.ejps.2007.06.002. [PMID: 17644326]
Branka Bedenic, Marijana Topic, Ana Budimir, Marina Bubonja. Urinary bactericidal activity of oral antibiotics against common urinary tract pathogens in an ex vivo model. Chemotherapy. 2006; 52(6):293-7. doi: 10.1159/000095969. [PMID: 17008781]
Masaki Kobayashi, Yoshitaka Saito, Shirou Itagaki, Takeshi Hirano, Ken Iseki. Nateglinide uptake by a ceftibuten transporter in the rat kidney brush-border membrane. Biochimica et biophysica acta. 2005 Aug; 1715(1):19-24. doi: 10.1016/j.bbamem.2005.05.013. [PMID: 16087153]
Yuriko Shimizu, Satohiro Masuda, Kumiko Nishihara, Lin Ji, Masahiro Okuda, Ken-Ichi Inui. Increased protein level of PEPT1 intestinal H+-peptide cotransporter upregulates absorption of glycylsarcosine and ceftibuten in 5/6 nephrectomized rats. American journal of physiology. Gastrointestinal and liver physiology. 2005 Apr; 288(4):G664-70. doi: 10.1152/ajpgi.00270.2004. [PMID: 15528259]
Shirou Itagaki, Yoshitaka Saito, Sayaka Kubo, Yukio Otsuka, Yuta Yamamoto, Masaki Kobayashi, Takeshi Hirano, Ken Iseki. H+-dependent transport mechanism of nateglinide in the brush-border membrane of the rat intestine. The Journal of pharmacology and experimental therapeutics. 2005 Jan; 312(1):77-82. doi: 10.1124/jpet.104.074021. [PMID: 15316092]
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]
Xiaoyue Pan, Tomohiro Terada, Masahiro Okuda, Ken-ichi Inui. Altered diurnal rhythm of intestinal peptide transporter by fasting and its effects on the pharmacokinetics of ceftibuten. The Journal of pharmacology and experimental therapeutics. 2003 Nov; 307(2):626-32. doi: 10.1124/jpet.103.055939. [PMID: 12970381]
E Ninkova, B Stambolov, Kh Vasilev. [Treatment of obstetric and gynecologic diseases with anti-inflammatory drug cedax]. Akusherstvo i ginekologiia. 2002; 41 Suppl 1(?):6-7. doi: NULL. [PMID: 12412345]
Akira Tsuji. Transporter-mediated Drug Interactions. Drug metabolism and pharmacokinetics. 2002; 17(4):253-74. doi: 10.2133/dmpk.17.253. [PMID: 15618677]
M W Ho, F D Wang, C P Fung, C Y Liu. Comparative study of ceftibuten and cefixime in the treatment of complicated urinary tract infections. Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi. 2001 Sep; 34(3):185-9. doi: . [PMID: 11605809]
A Vilaichone, D Watana, T Chaiwatanarat. Oral ceftibuten switch therapy for acute pyelonephritis in children. Journal of the Medical Association of Thailand = Chotmaihet thangphaet. 2001 Jun; 84 Suppl 1(?):S61-7. doi: . [PMID: 11529382]
K Koga, T Ohyashiki, M Murakami, S Kawashima. Modification of ceftibuten transport by the addition of non-ionic surfactants. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2000 Jan; 49(1):17-25. doi: 10.1016/s0939-6411(99)00059-4. [PMID: 10613923]
P Krumpe, C C Lin, E Radwanski, M N Cayen, M B Affrime. The penetration of ceftibuten into the respiratory tract. Chest. 1999 Aug; 116(2):369-74. doi: 10.1378/chest.116.2.369. [PMID: 10453864]
F Scaglione, G Demartini, S Dugnani, M M Arcidiacono, J P Pintucci, F Fraschini. Interpretation of middle ear fluid concentrations of antibiotics: comparison between ceftibuten, cefixime and azithromycin. British journal of clinical pharmacology. 1999 Mar; 47(3):267-71. doi: 10.1046/j.1365-2125.1999.00887.x. [PMID: 10215750]
K Koga, M Murakami, S Kawashima. Modification of ceftibuten transport by changes in lipid fluidity caused by fatty acid glycerol esters. Biological & pharmaceutical bulletin. 1999 Jan; 22(1):103-6. doi: 10.1248/bpb.22.103. [PMID: 9989674]
K Koga, M Murakami, S Kawashima. Effects of fatty acid sucrose esters on ceftibuten transport by rat intestinal brush-border membrane vesicles. Biological & pharmaceutical bulletin. 1998 Jul; 21(7):747-51. doi: 10.1248/bpb.21.747. [PMID: 9703261]
E Radwanski, A Nomeir, D Cutler, M Affrime, C C Lin. Pharmacokinetic drug interaction study: administration of ceftibuten concurrently with the antacid mylanta double- strength liquid or with ranitidine. American journal of therapeutics. 1998 Mar; 5(2):67-72. doi: NULL. [PMID: 10099040]
K Iseki, I Naasani, T Kikuchi, M Sugawara, M Kobayashi, N Kohri, K Miyazaki. Purification and liposomal reconstitution of the oligopeptide transport activity in rat renal cortex using ceftibuten-affinity chromatography. Biochimica et biophysica acta. 1998 Jan; 1368(2):329-37. doi: 10.1016/s0005-2736(97)00201-0. [PMID: 9459609]
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]
R C Owens, C H Nightingale, D P Nicolau. Ceftibuten: an overview. Pharmacotherapy. 1997 Jul; 17(4):707-20. doi: . [PMID: 9250548]
T Terada, H Saito, M Mukai, K Inui. Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. The Journal of pharmacology and experimental therapeutics. 1997 Jun; 281(3):1415-21. doi: . [PMID: 9190878]
M E Ganapathy, P D Prasad, B Mackenzie, V Ganapathy, F H Leibach. Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochimica et biophysica acta. 1997 Mar; 1324(2):296-308. doi: 10.1016/s0005-2736(96)00234-9. [PMID: 9092716]
D E Nix, W T Symonds, J M Hyatt, J H Wilton, M A Teal, P Reidenberg, M B Affrime. Comparative pharmacokinetics of oral ceftibuten, cefixime, cefaclor, and cefuroxime axetil in healthy volunteers. Pharmacotherapy. 1997 Jan; 17(1):121-5. doi: . [PMID: 9017772]
F Scaglione, J P Pintucci, G Demartini, S Dugnani. Ceftibuten concentrations in human tonsillar tissue. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology. 1996 Dec; 15(12):940-3. doi: 10.1007/bf01690513. [PMID: 9031878]
C C Lin, M Affrime, E Radwanski, J Lim, R Colucci, M N Cayen. Comparative bioavailability of ceftibuten in capsule and suspension forms. Clinical therapeutics. 1996 Nov; 18(6):1139-49. doi: 10.1016/s0149-2918(96)80068-3. [PMID: 9001830]
T Terada, H Saito, M Mukai, K I Inui. Identification of the histidine residues involved in substrate recognition by a rat H+/peptide cotransporter, PEPT1. FEBS letters. 1996 Sep; 394(2):196-200. doi: 10.1016/0014-5793(96)00952-0. [PMID: 8843163]
I Naasani, T Kikuchi, M Sugawara, M Kobayashi, K Iseki, K Miyazaki. Solubilization and reconstitution characteristics of the carrier protein(s) responsible for the transport of ceftibuten, a substrate for the oligopeptide transporters, in rat renal brush-border membrane. Biochimica et biophysica acta. 1996 Sep; 1283(2):185-91. doi: 10.1016/0005-2736(96)00092-2. [PMID: 8809098]
C Lin, P Kumari, R J Perrotta, B E Reidenberg. Penetration of ceftibuten into middle ear fluid. Antimicrobial agents and chemotherapy. 1996 Jun; 40(6):1394-6. doi: 10.1128/aac.40.6.1394. [PMID: 8726007]
H Saito, M Okuda, T Terada, S Sasaki, K Inui. Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. The Journal of pharmacology and experimental therapeutics. 1995 Dec; 275(3):1631-7. doi: . [PMID: 8531138]
I Naasani, K Sato, K Iseki, M Sugawara, M Kobayashi, K Miyazaki. Comparison of the transport characteristics of ceftibuten in rat renal and intestinal brush-border membranes. Biochimica et biophysica acta. 1995 Sep; 1231(2):163-8. doi: 10.1016/0005-2728(95)00073-r. [PMID: 7662695]
B E Reidenberg. Worldwide safety experience with ceftibuten pediatric suspension. The Pediatric infectious disease journal. 1995 Jul; 14(7 Suppl):S130-3. doi: 10.1097/00006454-199507001-00010. [PMID: 7567313]
W H Barr, M Affrime, C C Lin, V Batra. Pharmacokinetics of ceftibuten in children. The Pediatric infectious disease journal. 1995 Jul; 14(7 Suppl):S93-101. doi: 10.1097/00006454-199507001-00005. [PMID: 7567317]
N X Chin, H B Huang, H C Neu. Postantibiotic effect of ceftibuten on respiratory pathogens. The Pediatric infectious disease journal. 1995 Jul; 14(7 Suppl):S84-7. doi: 10.1097/00006454-199507001-00003. [PMID: 7567315]
F Scaglione, F Triscari, G Demartini, M Arcidiacono, C Cocuzza, F Fraschini. Concentrations of ceftibuten in bronchial secretions. Chemotherapy. 1995 Jul; 41(4):229-33. doi: 10.1159/000239349. [PMID: 7555201]
I Naasani, M Sugawara, M Kobayashi, K Iseki, K Miyazaki. Transport mechanism of ceftibuten, a dianionic cephem, in rat renal brush-border membrane. Pharmaceutical research. 1995 Apr; 12(4):605-8. doi: 10.1023/a:1016274517918. [PMID: 7596999]
C Lin, J Lim, E Radwanski, A Marco, M Affrime. Pharmacokinetics and dose proportionality of ceftibuten in men. Antimicrobial agents and chemotherapy. 1995 Feb; 39(2):359-61. doi: 10.1128/aac.39.2.359. [PMID: 7726498]
C Lin, E Radwanski, M Affrime, M N Cayen. Multiple-dose pharmacokinetics of ceftibuten in healthy volunteers. Antimicrobial agents and chemotherapy. 1995 Feb; 39(2):356-8. doi: 10.1128/aac.39.2.356. [PMID: 7726497]
F Bressolle, M Galtier, J M Kinowski, F Goncalves, L Edno, R Panis, R Gomeni. Multiple-dose pharmacokinetics of ceftibuten after oral administration to healthy volunteers. Journal of pharmaceutical sciences. 1994 Sep; 83(9):1236-40. doi: 10.1002/jps.2600830910. [PMID: 7830237]
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M Sugawara, A Hashimoto, M Kobayashi, K Iseki, K Miyazaki. Effect of membrane surface potential on the uptake of anionic compounds by liposomes. Biochimica et biophysica acta. 1994 Jun; 1192(2):241-6. doi: 10.1016/0005-2736(94)90124-4. [PMID: 7517186]
C O Onyeji, D P Nicolau, C H Nightingale, R Quintiliani. Optimal times above MICs of ceftibuten and cefaclor in experimental intra-abdominal infections. Antimicrobial agents and chemotherapy. 1994 May; 38(5):1112-7. doi: 10.1128/aac.38.5.1112. [PMID: 8067747]
J M Kinowski, F Bressolle, D Fabre, F Goncalves, R Rouzier-Panis, M Galtier. High-performance liquid chromatographic determination of ceftibuten and its metabolite in biological fluids: applications in pharmacokinetic studies. Journal of pharmaceutical sciences. 1994 May; 83(5):736-41. doi: 10.1002/jps.2600830529. [PMID: 8071832]
J M Lim, H Kim, A Marco, P Mojaverian, C C Lin. Liquid chromatographic determination of ceftibuten, a new oral cephalosporin, in human plasma and urine. Journal of pharmaceutical and biomedical analysis. 1994 May; 12(5):699-703. doi: 10.1016/0731-7085(93)e0005-8. [PMID: 7948191]
K Iseki, Y Satoh, M Sugawara, K Miyazaki. [Effect of Enterued administration on the intestinal absorption of orally active cefem antibiotics]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1994 Apr; 114(4):233-40. doi: 10.1248/yakushi1947.114.4_233. [PMID: 8201544]
G L Kearns, R A Young. Ceftibuten pharmacokinetics and pharmacodynamics. Focus on paediatric use. Clinical pharmacokinetics. 1994 Mar; 26(3):169-89. doi: 10.2165/00003088-199426030-00002. [PMID: 8194281]
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J S Kelloway, W M Awni, C C Lin, J Lim, M B Affrime, W F Keane, G R Matzke, C E Halstenson. Pharmacokinetics of ceftibuten-cis and its trans metabolite in healthy volunteers and in patients with chronic renal insufficiency. Antimicrobial agents and chemotherapy. 1991 Nov; 35(11):2267-74. doi: 10.1128/aac.35.11.2267. [PMID: 1803999]
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K Bachmann, J Schwartz, L Jauregui, M Martin, M Nunlee. Failure of ceftibuten to alter single dose theophylline clearance. Journal of clinical pharmacology. 1990 May; 30(5):444-8. doi: 10.1002/j.1552-4604.1990.tb03483.x. [PMID: 2347955]
S Mizutani, K Nishimura, K Yoshimura, S Miyoshi, N Iwao, J Higashimoto, K Shiota. [Clinical experience with ceftibuten in complicated urinary tract infections]. The Japanese journal of antibiotics. 1990 May; 43(5):779-89. doi: . [PMID: 2391749]
S G Bragman, M W Casewell. The in-vitro activity of ceftibuten against 475 clinical isolates of gram-negative bacilli, compared with cefuroxime and cefadroxil. The Journal of antimicrobial chemotherapy. 1990 Feb; 25(2):221-6. doi: 10.1093/jac/25.2.221. [PMID: 2329100]
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