Bacampicillin (BioDeep_00000006666)

 

Secondary id: BioDeep_00001868385

human metabolite blood metabolite


代谢物信息卡片


1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

化学式: C21H27N3O7S (465.157)
中文名称: 巴氨西林
谱图信息: 最多检出来源 Homo sapiens(blood) 9.46%

分子结构信息

SMILES: CCOC(=O)OC(C)OC(=O)C1C(SC2N1C(=O)C2NC(=O)C(C3=CC=CC=C3)N)(C)C
InChI: InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1

描述信息

Bacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.
J - Antiinfectives for systemic use > J01 - Antibacterials for systemic use > J01C - Beta-lactam antibacterials, penicillins > J01CA - Penicillins with extended spectrum
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

同义名列表

22 个代谢物同义名

1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 1-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanic acid; 1-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanic acid; 1-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanate; 1-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanic acid; 1-Ethoxycarbonyloxyethyl-(6-D-a-aminophenylacetamido)penicillanate; 1-Ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanate; Ethoxycarbonyloxyethyl ester OF ampicillin; Bacampicillin monohydrochloride; Bacampicillin hydrochloride; Bacampicillinum; Bacampicilline; CHEMBL1625790; Carampicillin; Bacampicillin; Bacampicilina; Bacampicine; Penglobe; BAPC; Bacampicillin



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

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)

2 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
Cytoplasm 4 ALB, AXIN2, CCL5, GLA
Peripheral membrane protein 1 ACHE
Endoplasmic reticulum membrane 2 CD4, GLA
Nucleus 3 ACHE, ALB, AXIN2
cytosol 2 ALB, AXIN2
centrosome 2 ALB, AXIN2
Cell membrane 5 ACHE, CD4, CD86, CR2, TNF
Multi-pass membrane protein 1 UCP1
Synapse 1 ACHE
cell surface 4 ACHE, CD86, TNF, TNFRSF4
Golgi apparatus 3 ACHE, ALB, GLA
mitochondrial inner membrane 1 UCP1
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
Lysosome 1 GLA
plasma membrane 11 ACHE, AXIN2, CD4, CD86, CR2, CSF2, FCER2, ICAM3, IFNLR1, TNF, TNFRSF4
Membrane 8 ACHE, CD86, CR2, FCER2, GLA, ICAM3, IFNLR1, TNFRSF4
extracellular exosome 6 ALB, CD86, CR2, FCER2, GLA, ICAM3
endoplasmic reticulum 1 ALB
extracellular space 10 ACHE, ALB, CCL5, CR2, CSF2, IL17A, IL17D, IL2, IL5, TNF
lysosomal lumen 1 GLA
perinuclear region of cytoplasm 1 ACHE
mitochondrion 1 UCP1
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 1 CSF2
Single-pass type I membrane protein 4 CD4, CD86, ICAM3, IFNLR1
Secreted 10 ACHE, ALB, CCL5, CR2, CSF2, FCER2, IL17A, IL2, IL23A, IL5
extracellular region 11 ACHE, ALB, CCL5, CR2, CSF2, GLA, IL17A, IL2, IL23A, IL5, TNF
Extracellular side 1 ACHE
anchoring junction 1 ALB
centriolar satellite 1 CD86
external side of plasma membrane 6 CD4, CD86, FCER2, IL17A, TNF, TNFRSF4
beta-catenin destruction complex 1 AXIN2
Early endosome 1 CD4
recycling endosome 1 TNF
Single-pass type II membrane protein 2 FCER2, TNF
Mitochondrion inner membrane 1 UCP1
Membrane raft 2 CD4, TNF
basement membrane 1 ACHE
receptor complex 1 CR2
ciliary basal body 1 ALB
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Lipid-anchor, GPI-anchor 1 ACHE
side of membrane 1 ACHE
endoplasmic reticulum lumen 3 ALB, CD4, IL23A
platelet alpha granule lumen 1 ALB
azurophil granule lumen 1 GLA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GLA
clathrin-coated endocytic vesicle membrane 1 CD4
endoplasmic reticulum-Golgi intermediate compartment 1 GLA
synaptic cleft 1 ACHE
granulocyte macrophage colony-stimulating factor receptor complex 1 CSF2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
[Isoform H]: Cell membrane 1 ACHE
interleukin-23 complex 1 IL23A
ciliary transition fiber 1 ALB
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

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  • N H Pham, B A Baldo. beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies. Journal of molecular recognition : JMR. 1996 Jul; 9(4):287-96. doi: 10.1002/(sici)1099-1352(199607)9:4\%3c287::aid-jmr340\%3e3.0.co;2-l. [PMID: 9131470]
  • P Sarasola, Q A McKellar. Pharmacokinetics of bacampicillin in equids. American journal of veterinary research. 1995 Nov; 56(11):1486-92. doi: . [PMID: 8585661]
  • P Sarasola, Q A McKellar. Ampicillin and its congener prodrugs in the horse. The British veterinary journal. 1994 Mar; 150(2):173-87. doi: 10.1016/s0007-1935(05)80225-8. [PMID: 8025849]
  • Y Akimoto, Y Mochizuki, A Uda, J Shibutani, H Nishimura, M Komiya, K Kaneko, A Fujii, H Yamamoto. Ampicillin concentrations in radicular cysts following a single oral administration of bacampicillin. General pharmacology. 1993 Jul; 24(4):895-8. doi: 10.1016/0306-3623(93)90166-u. [PMID: 8224746]
  • Y Akimoto, K Kaneko, A Fujii, H Yamamoto. Ampicillin concentrations in human radicular granuloma following a single oral dose of bacampicillin. Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons. 1992 Jan; 50(1):11-3. doi: 10.1016/0278-2391(92)90185-3. [PMID: 1727454]
  • S Kawashima, M Sugimura, T Noguchi, H Fujiwara. Studies on sustained-release suppositories. II. Evaluation of polymer electrolyte containing acidic groups for prolonged rectal absorption of bacampicillin in rabbits. Chemical & pharmaceutical bulletin. 1989 Jul; 37(7):1899-903. doi: 10.1248/cpb.37.1899. [PMID: 2805169]
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  • S Kawashima, N Nishiura, T Noguchi, H Fujiwara. Studies on sustained-release suppositories. I. Effect of alginic acid addition on rectal absorption of bacampicillin in rabbits. Chemical & pharmaceutical bulletin. 1989 Mar; 37(3):766-70. doi: 10.1248/cpb.37.766. [PMID: 2752491]
  • O Paulsen, P Höglund, M Walder. No effect of omeprazole-induced hypoacidity on the bioavailability of amoxycillin or bacampicillin. Scandinavian journal of infectious diseases. 1989; 21(2):219-23. doi: 10.3109/00365548909039972. [PMID: 2727638]
  • W Hofstra, G W Welling, D Van der Waaij. A comparative study of the effect of oral treatment with augmentin, amoxycillin and bacampicillin on the faecal flora in mice. Zentralblatt fur Bakteriologie, Mikrobiologie, und Hygiene. Series A, Medical microbiology, infectious diseases, virology, parasitology. 1988 Jul; 269(1):78-85. doi: 10.1016/s0176-6724(88)80086-5. [PMID: 3051802]
  • O Paulsen, L Borgström, B Kågedal, M Walder. No effect of oral N-acetylcysteine on the bioavailability of erythromycin and bacampicillin. The European respiratory journal. 1988 Feb; 1(2):171-5. doi: . [PMID: 3360092]
  • M del Piano, R Nicosia, R Sessa, G Grippaudo, R Lolli, B Monaco. Study on tissue concentrations of antibiotics: bacampicillin in gingiva and maxillary bones. Chemotherapy. 1988; 34(1):13-7. doi: 10.1159/000238541. [PMID: 3349860]
  • S Ripa, L Ferrante, F Mignini, U Ecari, M P Ruffilli. Pharmacokinetics of bacampicillin using a compartment model with zero-order absorption. Chemotherapy. 1988; 34(2):85-9. doi: 10.1159/000238552. [PMID: 3391055]
  • A Scordamaglia, G Ciprandi, S Mirabelli, R Aquilina, L Calcagno, A Nicolini, C Simonassi, M De Palma. Bacampicillin and the immune response. The Journal of antimicrobial chemotherapy. 1987 Jun; 19(6):791-3. doi: 10.1093/jac/19.6.791. [PMID: 3497151]
  • J Seppänen, O Hällström, J Sjövall, T Vaalasti. Intrarenal concentration-time profile of ampicillin after administration of bacampicillin to patients before nephrectomy. Journal of clinical pharmacology. 1986 Mar; 26(3):227-30. doi: 10.1002/j.1552-4604.1986.tb02939.x. [PMID: 3958226]
  • Y Akimoto, M Komiya, K Kaneko, A Fujii, T Tamura. Ampicillin concentrations in human serum, gingiva, mandibular bone, dental follicle, and dental pulp following a single oral administration of bacampicillin. Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons. 1986 Feb; 44(2):107-12. doi: 10.1016/0278-2391(86)90191-6. [PMID: 3456015]
  • Y Akimoto, J Shibutani, H Nishimura, M Komiya, T Shibata, H Tadokoro, K Kaneko, A Fujii, T Tamura. Ampicillin concentrations in human serum and periodontal membrane following a single oral administration of bacampicillin. General pharmacology. 1986; 17(2):227-9. doi: 10.1016/0306-3623(86)90143-6. [PMID: 3699449]
  • J Sjövall, G Alván, D Westerlund. Dose-dependent absorption of amoxycillin and bacampicillin. Clinical pharmacology and therapeutics. 1985 Sep; 38(3):241-50. doi: 10.1038/clpt.1985.166. [PMID: 4028617]
  • 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 Tauchnitz, R Ezold, V Kleint. [Bacampicillin in urinary tract infections tolerance in patients with impaired kidney and liver function]. Immunitat und Infektion. 1984 Nov; 12(6):303-8. doi: . [PMID: 6392071]
  • M Nicklasson, K Ellström, R Sjöqvist, J Sjövall. Linear systems analysis and moment analysis in the evaluation of bacampicillin bioavailability from microcapsule suspensions. Journal of pharmacokinetics and biopharmaceutics. 1984 Oct; 12(5):467-78. doi: 10.1007/bf01060126. [PMID: 6520743]
  • D K Sommers, M van Wyk, J Moncrieff, H S Schoeman. Influence of food and reduced gastric acidity on the bioavailability of bacampicillin and cefuroxime axetil. British journal of clinical pharmacology. 1984 Oct; 18(4):535-9. doi: 10.1111/j.1365-2125.1984.tb02501.x. [PMID: 6091711]
  • J Sjövall, R Sjöqvist, B Huitfeldt, H Nyqvist. Correlation between the bioavailability of microencapsulated bacampicillin hydrochloride in suspension and in vitro microcapsule dissolution. Journal of pharmaceutical sciences. 1984 Feb; 73(2):141-5. doi: 10.1002/jps.2600730202. [PMID: 6707871]
  • J Sjövall, D Westerlund, G Alván, L Magni, C E Nord, J Sörstad. Rectal bioavailability of bacampicillin hydrochloride in man as determined by reversed-phase liquid chromatography. Chemotherapy. 1984; 30(3):137-47. doi: 10.1159/000238260. [PMID: 6734304]
  • S Kitamura, L H Hsu, Y Ishihara, F Takaku. [Experimental investigation on intrapulmonary and tracheobronchial distribution of ampicillin after administration of a beta-lactam antibiotic, bacampicillin]. The Japanese journal of antibiotics. 1983 Nov; 36(11):2965-70. doi: . [PMID: 6674527]
  • T Bergan, A Engeset, W Olszewski, J Sjövall. Distribution to human peripheral lymph of amoxycillin and of ampicillin from the oral prodrug bacampicillin. The Journal of antimicrobial chemotherapy. 1983 Nov; 12(5):497-502. doi: 10.1093/jac/12.5.497. [PMID: 6671926]
  • F Di Nola. [Update on antibiotic therapy. 12) Bacampicillin]. Minerva medica. 1982 Dec; 73(49-50):3539-43. doi: NULL. [PMID: 7155402]
  • M Onsrud, T Bergan, H Gjønnaess. Antibiotic levels in plasma and peritoneal fluid after amoxycillin, ampicillin, and bacampicillin treatment for pelvic inflammatory disease. Acta obstetricia et gynecologica Scandinavica. 1982; 61(3):247-51. doi: 10.3109/00016348209156566. [PMID: 7124355]
  • A Heimdahl, L Kager, A S Malmborg, C E Nord. Impact of different betalactam antibiotics on the normal human flora, and colonization of the oral cavity, throat and colon. Infection. 1982; 10(2):120-4. doi: 10.1007/bf01816741. [PMID: 6807848]
  • J Sjövall. Tissue levels after administration of bacampicillin, a prodrug of ampicillin, and comparisons with other aminopenicillins: a review. The Journal of antimicrobial chemotherapy. 1981 Nov; 8 Suppl C(?):41-58. doi: 10.1093/jac/8.suppl_c.41. [PMID: 7319988]
  • F Di Nola, E Capra, M L Soranzo, G Bosio, C Bramato, B Salassa, L Andrini, G Andreoni, M Eandi, E Musso. [Kinetic and clinical study of bacampicillin]. Minerva medica. 1981 Apr; 72(15):941-50. doi: . [PMID: 7219802]
  • A Schreiner, T Bergan, K B Hellum, A Digranes. Pharmacokinetics of ampicillin in serum and in dermal suction blisters after oral administration of bacampicillin. Reviews of infectious diseases. 1981 Jan; 3(1):125-31. doi: 10.1093/clinids/3.1.125. [PMID: 7221355]
  • H C Neu. The pharmacokinetics of bacampicillin. Reviews of infectious diseases. 1981 Jan; 3(1):110-6. doi: 10.1093/clinids/3.1.110. [PMID: 7012993]
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  • P C Braga, F Fraschini, G Ceccarelli, F Scaglione, G Scarpazza. Clinical pharmacokinetic evaluation of bacampicillin. Clinical therapeutics. 1981; 4(1):32-42. doi: NULL. [PMID: 7273067]
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  • P J Spengler, L D Edwards. Comparative study of bacampicillin and ampicillin in the treatment of uncomplicated gonorrhoea. The British journal of venereal diseases. 1980 Jun; 56(3):151-5. doi: 10.1136/sti.56.3.151. [PMID: 7000303]
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  • A Heimdahl, C E Nord, K Weilander. Effect of phenoxymethylpenicillin, bacampicillin and clindamycin on the oral, throat and colon microflora of man. Swedish dental journal. 1980; 4(1-2):39-52. doi: . [PMID: 6770480]
  • M Ehrnebo, S O Nilsson, L O Boréus. Pharmacokinetics of ampicillin and its prodrugs bacampicillin and pivampicillin in man. Journal of pharmacokinetics and biopharmaceutics. 1979 Oct; 7(5):429-51. doi: 10.1007/bf01062386. [PMID: 529016]
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  • T Bergan, A Engeset, W Olszewski, R Solberg. Pharmacokinetics of bacampicillin and bacmecillinam in plasma and peripheral lymph. Lymphology. 1979 Jun; 12(2):85-94. doi: NULL. [PMID: 226808]
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  • J S Tan, S J Salstrom. Bacampicillin, Ampicillin, Cephalothin, and Cephapirin levels in human blood and interstitial fluid. Antimicrobial agents and chemotherapy. 1979 Apr; 15(4):510-2. doi: 10.1128/aac.15.4.510. [PMID: 464583]
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