Bacampicillin
(Synonyms: 巴氨西林) 目录号 : GC33966
Bacampicillin是青霉素类抗生素,是Ampicillin的前药,具有口服生物有效性。
Cas No.:50972-17-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Bacampicillin is a penicillin antibiotic, is a prodrug of ampicillin with improved oral bioavailability.
| Cas No. | 50972-17-3 | SDF | |
| 别名 | 巴氨西林 | ||
| Canonical SMILES | O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC([C@H](N)C3=CC=CC=C3)=O)N1C2=O)OC(OC(OCC)=O)C | ||
| 分子式 | C21H27N3O7S | 分子量 | 465.52 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.1481 mL | 10.7407 mL | 21.4814 mL |
| 5 mM | 0.4296 mL | 2.1481 mL | 4.2963 mL |
| 10 mM | 0.2148 mL | 1.0741 mL | 2.1481 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The pharmacokinetics of Bacampicillin
Rev Infect Dis 1981 Jan-Feb;3(1):110-6.PMID:7012993DOI:10.1093/clinids/3.1.110.
Bacampicillin is an ethoxycarbonyloxyethyl ester of ampicillin that is rapidly converted to free ampicillin, the active agent, by nonspecific esterases present in serum and in the intestinal wall. The compound is absorbed more rapidly than ampicillin, with peak absorption occurring 45 min to 1 hr after administration of the drug, whereas the peak after administration of the parent compound is at 2 hr. Peak levels of drug in serum after a 400-mg dose of Bacampicillin (molar equivalent, 278 mg of ampicillin) are 6-8 micrograms/ml. Peak levels after an 800-mg dose of Bacampicillin (molar equivalent, 556 mg of ampicillin) are 11-14 micrograms/ml. These peak levels are twofold greater than those achieved with equimolar doses of ampicillin. Ingestion of Bacampicillin with food does not decrease or delay absorption of the drug. Recovery of ampicillin in urine after ingestion of Bacampicillin is 75% vs. a recovery of 45% after ampicillin. Ampicillin appears earlier in tears, saliva, bronchial and maxillary sinus secretions, middle ear fluid, skin blisters. lymph, and urethral and cervical secretions, and the levels obtained in these tissues are greater after ingestion of Bacampicillin than after ampicillin. The pharmacokinetics of Bacampicillin and ampicillin in the period 2.5-8 hr after their ingestion is virtually identical at equimolar doses.
Bacampicillin hydrochloride: chemistry, pharmacology, and clinical use
Pharmacotherapy 1982 Nov-Dec;2(6):313-21.PMID:6762528DOI:10.1002/j.1875-9114.1982.tb03206.x.
Bacampicillin hydrochloride is an orally administered ester of ampicillin that is rapidly and completely hydrolyzed in vivo to ampicillin. The most notable advantage of Bacampicillin over ampicillin is its superior bioavailability--bacampicillin achieves significantly higher blood and tissue levels and attains peak blood levels more rapidly than equimolar doses of oral ampicillin. In addition, the percentage of an oral dose of ampicillin that is absorbed decreases sharply as the size of the dose is increased from 500 mg to 2 g; this phenomenon is not observed with equipotent doses of Bacampicillin. The enhanced absorption of Bacampicillin in the upper gastrointestinal tract results in a frequency of diarrhea that appears to be markedly lower than that of ampicillin and similar to that observed with amoxicillin. Apart from the sizable differences between Bacampicillin and ampicillin with regard to oral absorption, the pharmacokinetic and pharmacologic profiles of these two agents are essentially identical. Twice daily dosing (pulse dosing) with Bacampicillin has been shown in numerous clinical trials to be of equivalent efficacy to ampicillin given four times daily or amoxicillin given three times daily in the treatment of infections of the upper respiratory tract, lower respiratory tract, skin and soft tissues, and urinary tract. The unanswered question is whether twice daily ampicillin or amoxicillin would yield similar results.
Bacampicillin uptake is shared with thiamine in Caco-2 cells
Biol Pharm Bull 2007 Jul;30(7):1344-9.PMID:17603179DOI:10.1248/bpb.30.1344.
Bacampicillin was developed as a prodrug to improve the intestinal absorption of its metabolite ampicillin. This study was undertaken to characterize Bacampicillin transport in Caco-2 cells. The uptake of Bacampicillin in Caco-2 cells was significantly greater than those of ampicillin and pivampicillin. An Eadie-Hofstee plot obtained from 5-min uptake of 0.2-5 mM Bacampicillin was linear, indicating the presence of a saturable transport system for Bacampicillin with K(m) and V(max) of 3.6 mM and 23.9 nmol/mg protein/min, respectively. Hydrophilic organic cations such as choline, cimetidine, guanidine, nicotinamide, 1-methylnicotiamide, and tetraethylammonium failed to modulate Bacampicillin uptake in Caco-2 cells whereas diphenhydramine, procainamide, and thiamine significantly depressed it. Moreover, when thiamine was preloaded in Caco-2 cells, Bacampicillin uptake was significantly increased, indicating that this cationic vitamin was capable of trans-stimulating Bacampicillin transport across the apical membrane of Caco-2 cells. However, trans-stimulated Bacampicillin uptake was not observed in the presence of diphenhydramine. Bacampicillin uptake increased with elevation of the medium pH, and the known modulators of thiamine transport such as amiloride and oxythiamine significantly inhibited Bacampicillin uptake. Thiamine also significantly decreased the apical-to-basolateral transport of Bacampicillin across Caco-2 cell monolayers. However, thiamine did not exert any modulating effect on pivampicillin uptake and its apical-to-basolateral permeation in Caco-2 cells. These results suggest that Bacampicillin is transported in Caco-2 cells, sharing a carrier-mediated system with thiamine.
Bacampicillin: a new orally well-absorbed derivative of ampicillin
Antimicrob Agents Chemother 1975 Nov;8(5):518-25.PMID:1211909DOI:10.1128/AAC.8.5.518.
Bacampicillin (proposed international nonproprietary name), 1'-ethoxycarbonyloxyethyl 6-(d-alpha-aminophenylacetamido)penicillanate, is a new orally well-absorbed penicillin, highly active in vivo due to rapid transformation into ampicillin. The compound is stable in vitro at gastric pH and hydrolyzed slowly to ampicillin at neutral pH but very rapidly in the presence of biological fluids, e.g., tissue homogenates or serum. In vivo the transformation into ampicillin is so rapid that no unchanged compound could be detected in the blood after oral administration of Bacampicillin to rats, dogs, and humans. On oral administration to mice, rats, and dogs, Bacampicillin was found to be better absorbed than ampicillin, giving higher and earlier peak blood levels of ampicillin. The bioavailability of Bacampicillin in rats and dogs was three to four times higher than that of an equimolar amount of ampicillin. On oral administration to rats, Bacampicillin was found to give higher levels of ampicillin in organs such as the kidney, liver, and spleen than ampicillin itself. In "tissue cages" in rats, higher transudate levels of antibiotic were found after oral administration of Bacampicillin than after ampicillin. On oral treatment of experimentally infected mice, Bacampicillin was found to be more active than ampicillin.
Bacampicillin and ampicillin in urinary tract infections: a double-blind comparison of efficacy and tolerance
Infection 1979;7 Suppl 5:S489-91.PMID:389825DOI:10.1007/BF01659780.
A total of 100 hospitalized patients with upper and lower urinary tract infections were treated with Bacampicillin or ampicillin. The treatment was double-blind and 50 patients were randomly allocated to each group, receiving 800 mg of Bacampicillin or 2 g of ampicillin t. i. d. for ten days. The distribution by age and sex was similar in the two groups. Assessments of therapeutic response and tolerance were made two and six weeks after initiation of therapy. In 89% of the patients treated with Bacampicillin and 68% of the ampicillin-treated patients both the bacteria and the symptoms were eliminated at the first follow-up visit three days after end of therapy. Relapse of reinfection occurred in 44% of the ampicillin-treated patients as compared to 7% in the bacampicillin-treated patients. Side-effects occurred significantly less frequently with Bacampicillin compared with ampicillin (p less than 0.05). Treatment had to be stopped on account of side-effects in 16 patients treated with ampicillin compared with only four patients treated with Bacampicillin.