Cefprozil (BioDeep_00000006370)

 

Secondary id: BioDeep_00001028661

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

化学式: C18H19N3O5S (389.10453640000003)
中文名称: 头孢曲唑
谱图信息: 最多检出来源 Homo sapiens(blood) 88.89%

分子结构信息

SMILES: CC=CC1=C(C(=O)O)N2C(=O)C(NC(=O)C(N)c3ccc(O)cc3)C2SC1
InChI: InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1

描述信息

Cefprozil is only found in individuals that have used or taken this drug. It is a cephalosporin antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.Cefprozil, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefprozil interferes with an autolysin inhibitor.
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,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-(2-Amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; 7-(2-Amino-2-(4-hydroxyphenyl)acetamido)-3-(propenyl)-3-cephem-4-carboxylic acid monohydrate; Cefprozil monohydrate; Cefprozil (Z)-Isomer; Cefprozil anhydrous; (Z)-Cefprozil; Cefprozilum; Cefprozilo; Cefprozil; Brisoral; Arzimol; Cefzil; Procef



数据库引用编号

17 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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WikiPathways(0)

Plant Reactome(0)

INOH(0)

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1 个相关的物种来源信息

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  • 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。

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文献列表

  • Lili Yang, Guanglin Zhou, Jinghua Liu, Jinshuang Song, Zongyu Zhang, Qi Huang, Fengxiang Wei. Tanshinone I and Tanshinone IIA/B attenuate LPS-induced mastitis via regulating the NF-κB. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111353. doi: 10.1016/j.biopha.2021.111353. [PMID: 33578236]
  • Ping-Ping Lin, Chen-Jing Wang, Yan-Ping Liu, Ting Li, Xiao-Meng Gao, Ya-Ping Ma, Ping Shi, Xin Li, Le-Xin Wang, Yu Cao. Pharmacokinetics and Bioequivalence of Cefprozil for Suspension and Granule Formulation in Healthy Chinese Volunteers: Two Single-Dose Crossover Studies. Advances in therapy. 2021 02; 38(2):1130-1142. doi: 10.1007/s12325-020-01593-7. [PMID: 33340343]
  • Alan K Jarmusch, Alison Vrbanac, Jeremiah D Momper, Joseph D Ma, Maher Alhaja, Marlon Liyanage, Rob Knight, Pieter C Dorrestein, Shirley M Tsunoda. Enhanced Characterization of Drug Metabolism and the Influence of the Intestinal Microbiome: A Pharmacokinetic, Microbiome, and Untargeted Metabolomics Study. Clinical and translational science. 2020 09; 13(5):972-984. doi: 10.1111/cts.12785. [PMID: 32216086]
  • Fei-Fei Jia, Zhi-Rong Tan, Howard L McLeod, Yao Chen, Dong-Sheng Ou-Yang, Hong-Hao Zhou. Effects of quercetin on pharmacokinetics of cefprozil in Chinese-Han male volunteers. Xenobiotica; the fate of foreign compounds in biological systems. 2016 Oct; 46(10):896-900. doi: 10.3109/00498254.2015.1132792. [PMID: 26928207]
  • Min Liu, Jing-Yi Ma, Yanan Zhang, Xiaolin Wang, Hongna Zhao, Aihua Du, Man Yang, Lingjie Meng, Ming Deng, Huichen Liu. An LC-MS/MS method for simultaneous determination of cefprozil diastereomers in human plasma and its application for the bioequivalence study of two cefprozil tablets in healthy Chinese volunteers. Biomedical chromatography : BMC. 2016 Mar; 30(3):288-93. doi: 10.1002/bmc.3547. [PMID: 26129932]
  • Frédéric Raymond, Amin A Ouameur, Maxime Déraspe, Naeem Iqbal, Hélène Gingras, Bédis Dridi, Philippe Leprohon, Pier-Luc Plante, Richard Giroux, Ève Bérubé, Johanne Frenette, Dominique K Boudreau, Jean-Luc Simard, Isabelle Chabot, Marc-Christian Domingo, Sylvie Trottier, Maurice Boissinot, Ann Huletsky, Paul H Roy, Marc Ouellette, Michel G Bergeron, Jacques Corbeil. The initial state of the human gut microbiome determines its reshaping by antibiotics. The ISME journal. 2016 Mar; 10(3):707-20. doi: 10.1038/ismej.2015.148. [PMID: 26359913]
  • David P Nicolau, Christina A Sutherland, Adriano Arguedas, Ron Dagan, Micheal E Pichichero. Pharmacokinetics of cefprozil in plasma and middle ear fluid: in children undergoing treatment for acute otitis media. Paediatric drugs. 2007; 9(2):119-23. doi: 10.2165/00148581-200709020-00005. [PMID: 17407367]
  • Philip Toltzis, Michael Dul, Mary Ann O'Riordan, Hasida Toltzis, Jeffrey L Blumer. Comparative effects of single-dose ceftriaxone versus three oral antibiotic regimens on stool colonization by resistant bacilli in children. The Pediatric infectious disease journal. 2007 Jan; 26(1):25-30. doi: 10.1097/01.inf.0000247130.11902.64. [PMID: 17195701]
  • Tae-Hwan Park, Jin-Ki Kim, Jun-Pil Jee, Jeong-Sook Park, Chong-Kook Kim. HPLC method for simultaneous determination of cefprozil diastereomers in human plasma. Journal of pharmaceutical and biomedical analysis. 2004 Sep; 36(1):243-8. doi: 10.1016/j.jpba.2004.06.001. [PMID: 15351073]
  • Chul Ho Jang, See Young Park. Penetration of cefprozil to middle ear effusion in children with chronic otitis media with effusion. International journal of pediatric otorhinolaryngology. 2003 Sep; 67(9):965-8. doi: 10.1016/s0165-5876(03)00163-0. [PMID: 12907051]
  • 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]
  • R Wise. Comparative microbiological activity and pharmacokinetics of cefprozil. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology. 1994 Oct; 13(10):839-45. doi: 10.1007/bf02111350. [PMID: 7889957]
  • W C Shyu, J Haddad, J Reilly, W N Khan, D A Campbell, Y Tsai, R H Barbhaiya. Penetration of cefprozil into middle ear fluid of patients with otitis media. Antimicrobial agents and chemotherapy. 1994 Sep; 38(9):2210-2. doi: 10.1128/aac.38.9.2210. [PMID: 7811050]
  • N Lowery, G L Kearns, R A Young, J G Wheeler. Serum sickness-like reactions associated with cefprozil therapy. The Journal of pediatrics. 1994 Aug; 125(2):325-8. doi: 10.1016/s0022-3476(94)70220-9. [PMID: 8040786]
  • W C Shyu, C R Gleason, R H Barbhaiya. Effects of time of administration and posture on the pharmacokinetics of cefprozil. Clinical pharmacokinetics. 1993 Sep; 25(3):237-42. doi: 10.2165/00003088-199325030-00006. [PMID: 8222462]
  • W C Shyu, J Reilly, D A Campbell, R B Wilber, R H Barbhaiya. Penetration of cefprozil into tonsillar and adenoidal tissues. Antimicrobial agents and chemotherapy. 1993 May; 37(5):1180-3. doi: 10.1128/aac.37.5.1180. [PMID: 8517711]
  • H Wakiguchi, N Ohishi, S Kido, T Takechi, K Takeda, K Yoshimura, I Nomura, M Fujieda, K Araki, T Kurashige. [Therapeutic effects of cefprozil in the treatment of various infectious diseases in children]. The Japanese journal of antibiotics. 1992 Dec; 45(12):1676-83. doi: . [PMID: 1289587]
  • K Nagano, H Maeda, T Yanagi, Y Tsuji, H Imamura, N Nakayama, M Yanagishima, S Fukuda. [Pharmacokinetic and clinical studies of cefprozil fine granules in children]. The Japanese journal of antibiotics. 1992 Dec; 45(12):1736-44. doi: . [PMID: 1289590]
  • T Motohiro, M Aramaki, K Oda, A Kawakami, T Koga, S Tomita, Y Sakata, F Yamashita, N Takajo, S Okabayashi. [Pharmacokinetic and clinical studies on cefprozil granules in the pediatric field]. The Japanese journal of antibiotics. 1992 Dec; 45(12):1700-35. doi: . [PMID: 1289589]
  • Y Kainou, S Matsumoto, K Kida, H Matsuda. [Basic and clinical studies on cefprozil in pediatrics]. The Japanese journal of antibiotics. 1992 Dec; 45(12):1667-75. doi: . [PMID: 1289586]
  • S Nakazawa, H Sato, A Narita, S Nakazawa, H Suzuki, K Matsumoto, K Niinou. [Clinical studies on cefprozil granules in pediatrics]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1514-25. doi: . [PMID: 1494234]
  • H Akita, Y Sato, S Iwata, K Sunakawa. [Laboratory and clinical studies on cefprozil granules in pediatrics]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1526-36. doi: . [PMID: 1494235]
  • F Hayakawa, K Kuno, A Ogawa, Y Nakao, Y Ando, H Ando. [Laboratory and clinical studies on cefprozil in the field of pediatrics]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1558-70. doi: . [PMID: 1494237]
  • T Nishimura, K Tabuki, S Aoki, M Takagi. [Laboratory and clinical studies of cefprozil in pediatric field]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1582-91. doi: . [PMID: 1494239]
  • R Fujii, H Meguro, T Tajima, H Shiraishi, T Abe, S Nakazawa, H Sato, K Niinou, K Matsumoto, K Sunakawa. [Overall clinical evaluation of cefprozil against infections in pediatric fields. Pediatric Study Group for Cefprozil]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1592-608. doi: NULL. [PMID: 1494240]
  • S Arai, R Sono, M Ito, M Sakurai, T Ihara, H Kamiya, S Shimizu, H Nishi, M Inoue, M Kojima. [Pharmacokinetic, bacteriological and clinical studies on cefprozil in pediatric patients]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1571-81. doi: . [PMID: 1494238]
  • S Iwata, M Ikeda, K Yamada, E Isohata, Y Kin, Y Kusumoto, Y Sato, H Akita, S Nanri, T Oikawa. [The influence of cefprozil on intestinal bacterial flora]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1474-88. doi: NULL. [PMID: 1494231]
  • H Nakamura, N Iwai. [Pharmacokinetic study on oral antibiotics in pediatrics. III. A pharmacokinetic study on cefprozil in pediatrics]. The Japanese journal of antibiotics. 1992 Nov; 45(11):1489-504. doi: NULL. [PMID: 1494232]
  • W C Shyu, V R Shah, D A Campbell, R B Wilber, K A Pittman, R H Barbhaiya. Oral absolute bioavailability and intravenous dose-proportionality of cefprozil in humans. Journal of clinical pharmacology. 1992 Sep; 32(9):798-803. doi: 10.1002/j.1552-4604.1992.tb03885.x. [PMID: 1430299]
  • U A Shukla, K A Pittman, R H Barbhaiya. Pharmacokinetic interactions of cefprozil with food, propantheline, metoclopramide, and probenecid in healthy volunteers. Journal of clinical pharmacology. 1992 Aug; 32(8):725-31. doi: 10.1002/j.1552-4604.1992.tb03876.x. [PMID: 1487562]
  • S L Barriere. Pharmacology and pharmacokinetics of cefprozil. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 1992 Jun; 14 Suppl 2(?):S184-8; discussion S195. doi: 10.1093/clinids/14.supplement_2.s184. [PMID: 1617036]
  • W C Shyu, V R Shah, D A Campbell, J Venitz, V Jaganathan, K A Pittman, R B Wilber, R H Barbhaiya. Excretion of cefprozil into human breast milk. Antimicrobial agents and chemotherapy. 1992 May; 36(5):938-41. doi: 10.1128/aac.36.5.938. [PMID: 1510416]
  • R H Barbhaiya, L Wang, W C Shyu, K A Pittman. Absolute bioavailability of cefprozil after oral administration in beagles. Antimicrobial agents and chemotherapy. 1992 Mar; 36(3):687-9. doi: 10.1128/aac.36.3.687. [PMID: 1622187]
  • H Lode, C Müller, K Borner, C E Nord, P Koeppe. Multiple-dose pharmacokinetics of cefprozil and its impact on intestinal flora of volunteers. Antimicrobial agents and chemotherapy. 1992 Jan; 36(1):144-9. doi: 10.1128/aac.36.1.144. [PMID: 1590680]
  • J C Christenson, W M Gooch, J N Herrod, E Swenson. Comparative efficacy and safety of cefprozil and cefaclor in the treatment of acute uncomplicated urinary tract infections. The Journal of antimicrobial chemotherapy. 1991 Oct; 28(4):581-6. doi: 10.1093/jac/28.4.581. [PMID: 1761453]
  • W C Shyu, U A Shukla, V R Shah, E A Papp, R H Barbhaiya. Simultaneous high-performance liquid chromatographic analysis of cefprozil diastereomers in a pharmacokinetic study. Pharmaceutical research. 1991 Aug; 8(8):992-6. doi: 10.1023/a:1015896722170. [PMID: 1924169]
  • J C Christenson, E Swenson, W M Gooch, J N Herrod. Comparative efficacy and safety of cefprozil (BMY-28100) and cefaclor in the treatment of acute group A beta-hemolytic streptococcal pharyngitis. Antimicrobial agents and chemotherapy. 1991 Jun; 35(6):1127-30. doi: 10.1128/aac.35.6.1127. [PMID: 1929253]
  • W C Shyu, R B Wilber, K A Pittman, D C Garg, R H Barbhaiya. Pharmacokinetics of cefprozil in healthy subjects and patients with hepatic impairment. Journal of clinical pharmacology. 1991 Apr; 31(4):372-6. doi: 10.1002/j.1552-4604.1991.tb03720.x. [PMID: 2037711]
  • W C Shyu, K A Pittman, R B Wilber, G R Matzke, R H Barbhaiya. Pharmacokinetics of cefprozil in healthy subjects and patients with renal impairment. Journal of clinical pharmacology. 1991 Apr; 31(4):362-71. doi: 10.1002/j.1552-4604.1991.tb03719.x. [PMID: 2037710]
  • 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]
  • T Motohiro, A Kawakami, H Sasaki, M Aramaki, Y Sakata, K Tominaga, F Yamashita. [Effect of BMY-28100 on bacterial flora in adult human feces]. The Japanese journal of antibiotics. 1990 Nov; 43(11):1898-913. doi: NULL. [PMID: 2287057]
  • X Sáez-Llorens, W C Shyu, S Shelton, H Kumiesz, J Nelson. Pharmacokinetics of cefprozil in infants and children. Antimicrobial agents and chemotherapy. 1990 Nov; 34(11):2152-5. doi: 10.1128/aac.34.11.2152. [PMID: 2073105]
  • T Motohiro, A Kawakami, H Sasaki, M Aramaki, Y Sakata, K Tominaga, F Yamashita, H Nakanomyo, M Hiraoka, K Ishikawa. [Pharmacokinetics of BMY-28100 in multiple administration]. The Japanese journal of antibiotics. 1990 Nov; 43(11):1893-7. doi: NULL. [PMID: 2287056]
  • H Nakanomyo, M Hiraoka, M Kidono. [Microbiological assay method of BMY-28100 and some other cephem antibiotic in serum and tissues. Development of new sample preparation with Evan's blue, a high albumin binding dye]. The Japanese journal of antibiotics. 1990 Sep; 43(9):1538-44. doi: . [PMID: 2262961]
  • S Kawano, H Kohmura, S Ohta, N Takahashi. [Immunological properties of BMY-28100 and cefepime]. The Japanese journal of antibiotics. 1990 Jul; 43(7):1275-88. doi: . [PMID: 2232157]
  • H Nakanomyo, K Ishikawa, Y Esumi, M Takaichi, Y Jin, S Gunji, H Ishikawa, J Sonobe. [Studies on the pharmacokinetics of BMY-28100 (I)]. The Japanese journal of antibiotics. 1990 Jul; 43(7):1310-24. doi: NULL. [PMID: 2232159]
  • H Nakanomyo, K Ishikawa, Y Esumi, M Takaichi, Y Jin, S Gunji, H Ishikawa, J Sonobe. [Studies on the pharmacokinetics of BMY-28100 (II)]. The Japanese journal of antibiotics. 1990 Jul; 43(7):1325-34. doi: NULL. [PMID: 2232160]
  • A Goto, M Amano, A Sakai, M Hara, N Takahashi. [General pharmacology of BMY-28100]. The Japanese journal of antibiotics. 1990 Jul; 43(7):1289-309. doi: NULL. [PMID: 2232158]
  • R H Barbhaiya, U A Shukla, C R Gleason, W C Shyu, R B Wilber, R R Martin, K A Pittman. Phase I study of multiple-dose cefprozil and comparison with cefaclor. Antimicrobial agents and chemotherapy. 1990 Jun; 34(6):1198-203. doi: 10.1128/aac.34.6.1198. [PMID: 2393281]
  • R H Barbhaiya, U A Shukla, C R Gleason, W C Shyu, K A Pittman. Comparison of the effects of food on the pharmacokinetics of cefprozil and cefaclor. Antimicrobial agents and chemotherapy. 1990 Jun; 34(6):1210-3. doi: 10.1128/aac.34.6.1210. [PMID: 2393283]
  • R H Barbhaiya, U A Shukla, C R Gleason, W C Shyu, R B Wilber, K A Pittman. Comparison of cefprozil and cefaclor pharmacokinetics and tissue penetration. Antimicrobial agents and chemotherapy. 1990 Jun; 34(6):1204-9. doi: 10.1128/aac.34.6.1204. [PMID: 2393282]
  • K Nye, P O'Neill, J M Andrews, R Wise. Pharmacokinetics and tissue penetration of cefprozil. The Journal of antimicrobial chemotherapy. 1990 May; 25(5):831-5. doi: 10.1093/jac/25.5.831. [PMID: 2373665]
  • R H Barbhaiya, C R Gleason, W C Shyu, R B Wilber, R R Martin, K A Pittman. Phase I study of single-dose BMY-28100, a new oral cephalosporin. Antimicrobial agents and chemotherapy. 1990 Feb; 34(2):202-5. doi: 10.1128/aac.34.2.202. [PMID: 2327766]
  • T Naito, H Hoshi, S Aburaki, Y Abe, J Okumura, K Tomatsu, H Kawaguchi. Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds. The Journal of antibiotics. 1987 Jul; 40(7):991-1005. doi: 10.7164/antibiotics.40.991. [PMID: 3624077]
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