Bacampicillin (BioDeep_00000006666)

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 (465.15696320000006)
中文名称: 巴氨西林
谱图信息: 最多检出来源 Homo sapiens(blood) 50%

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

21 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

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:2968
KEGG: C08122
KEGGdrug: D07487
PubChem: 441397
PubChem: 2282
HMDB: HMDB0015540
Metlin: METLIN612
DrugBank: DB01602
ChEMBL: CHEMBL1583
Wikipedia: Bacampicillin
chemspider: 390135
CAS: 50972-17-3
PMhub: MS000019744
PubChem: 10322
NIKKAJI: J14.626I

分类词条

Penicillins

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

7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
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

J M Ensink, A G Vulto, A S van Miert, J J Tukker, M B Winkel, M A Fluitman. Oral bioavailability and in vitro stability of pivampicillin, bacampicillin, talampicillin, and ampicillin in horses. American journal of veterinary research. 1996 Jul; 57(7):1021-4. doi: . [PMID: 8807014]
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]
Z M Sum, A M Sefton, A P Jepson, J D Williams. Comparative pharmacokinetic study between lenampicillin, bacampicillin and amoxycillin. The Journal of antimicrobial chemotherapy. 1989 Jun; 23(6):861-8. doi: 10.1093/jac/23.6.861. [PMID: 2759930]
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]
F Fraschini, P C Braga, V Copponi, M Maccari, D Piovani, F Scaglione, G Scarpazza. Bactericidal activity of erythromycin in the respiratory system. Current medical research and opinion. 1981; 7(7):429-39. doi: 10.1185/03007998109114280. [PMID: 6266774]
J S Tan, S J Salstrom, T M File. Levels of antibiotic in human blood and interstitial fluid after oral administration of bacampicillin or phenoxymethyl penicillin and intravenous administration of amoxicillin or ampicillin. Reviews of infectious diseases. 1981 Jan; 3(1):121-4. doi: 10.1093/clinids/3.1.121. [PMID: 6784223]
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]
C M Ginsburg, G H McCracken, J Clahsen, T Zweighaft. Comparative pharmacokinetics of bacampicillin and ampicillin suspensions in infants and children. Reviews of infectious diseases. 1981 Jan; 3(1):117-20. doi: 10.1093/clinids/3.1.117. [PMID: 7194499]
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]
O S Nielsen, N Frimodt-Moeller, S Maigaard, U Hoyme, A Baumueller, P O Madsen. Penicillanic acid derivatives in the canine prostate. The Prostate. 1980; 1(1):79-85. doi: 10.1002/pros.2990010111. [PMID: 6269107]
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]
A Nishio, Y Kumamoto, S Sakai, T Saka, M Terada, M Hikita. [Clinical investigation on a new penicillin derivative, bacampicillin (author's transl)]. The Japanese journal of antibiotics. 1979 Aug; 32(8):839-45. doi: . [PMID: 490899]
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]
S Nakazawa, H Sato, H Chikaoka, Y Hirama, A Narita. [An investigation on bacampicillin granules (author's transl)]. The Japanese journal of antibiotics. 1979 Apr; 32(4):541-5. doi: . [PMID: 459084]
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]
J Guibert, J F Acar. [Comparison of the serum and urinary concentrations of antibiotic after oral administration of bacampicillin and ampicillin]. Therapie. 1979 Jan; 34(1):89-94. doi: NULL. [PMID: 483228]
C Simon, V Malerczyk, M Klaus. [Clinical pharmacology of Bacampicillin in comparison to Ampicillin (author's transl)]. Medizinische Klinik. 1978 Jun; 73(24):910-3. doi: . [PMID: 661733]
A Swahn. Gastrointestinal absorption and metabolism of two 35S-labelled ampicillin esters. European journal of clinical pharmacology. 1976 Feb; 9(4):299-306. doi: 10.1007/bf00561664. [PMID: 9302]
L Accatino, F R Simon. Identification and characterization of a bile acid receptor in isolated liver surface membranes. The Journal of clinical investigation. 1976 Feb; 57(2):496-508. doi: 10.1172/jci108302. [PMID: 3520]