Bacampicillin是一种口服的前体药物，属于半合成青霉素类抗生素，在体内水解为活性代谢物氨苄西林，Bacampicillin通过抑制细菌细胞壁合成发挥杀菌作用。
Cas No.:37661-08-8
Sample solution is provided at 25 µL, 10mM.
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Bacampicillin is an oral prodrug belonging to the semisynthetic penicillin class of antibiotics. Bacampicillin is hydrolyzed in the body to Bacampicillin active metabolite, ampicillin. Bacampicillin exerts bactericidal action by inhibiting bacterial cell wall synthesis[1-2]. Bacampicillin is used in research related to infections caused by susceptible bacteria, such as respiratory tract infections, urinary tract infections, and skin and soft tissue infections[3-4].
In vitro, Caco-2 cells were incubated with Bacampicillin (0.2mM) for 5-10 minutes. The cellular uptake rate of Bacampicillin was significantly higher than that of Ampicillin. The transmembrane transport of Bacampicillin significantly increased as the pH of the culture medium was elevated[5].
In vivo, conventional female Swiss mice were orally treated with Bacampicillin (0-3mg/mouse/day) for 4 weeks starting from the 3rd week. The fecal microflora of the mice receiving Bacampicillin was almost unaffected. The interference of Bacampicillin with the normal protective intestinal flora was significantly less than that caused by ampicillin alone or its combination with clavulanic acid[6]. Fasted SPF rats were orally administered Bacampicillin (135mg/kg; single injection). Bacampicillin resulted in higher peak ampicillin concentration levels in the blood, kidneys, liver, and tissue fluid from subcutaneously implanted cages compared to treatment with an equimolar dose of ampicillin. In an experimental mouse infection model, when administered orally Bacampicillin (135mg/kg) 4 hours after infection with Haemophilus influenzae, Bacampicillin demonstrated higher anti-infective activity compared to ampicillin[7].
References:
[1] Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Bacampicillin. 2024 Sep 15.
[2] Scheife RT, Neu HC. Bacampicillin hydrochloride: chemistry, pharmacology, and clinical use. Pharmacotherapy. 1982 Nov-Dec;2(6):313-21.
[3] Neu HC. The pharmacokinetics of bacampicillin. Rev Infect Dis. 1981 Jan-Feb;3(1):110-6.
[4] Sum ZM, Sefton AM, Jepson AP, et al. Comparative pharmacokinetic study between lenampicillin, bacampicillin and amoxycillin. J Antimicrob Chemother. 1989 Jun;23(6):861-8.
[5] Oda M, Fujimoto K, Kobayashi M, et al. Bacampicillin uptake is shared with thiamine in Caco-2 cells. Biol Pharm Bull. 2007 Jul;30(7):1344-9.
[6] Hofstra W, Welling GW, Van der Waaij D. A comparative study of the effect of oral treatment with augmentin, amoxycillin and bacampicillin on the faecal flora in mice. Zentralbl Bakteriol Mikrobiol Hyg A. 1988 Jul;269(1):78-85.
[7] Bodin NO, Ekström B, Forsgren U, et al. Bacampicillin: a new orally well-absorbed derivative of ampicillin. Antimicrob Agents Chemother. 1975 Nov;8(5):518-25.
Bacampicillin是一种口服的前体药物，属于半合成青霉素类抗生素，在体内水解为活性代谢物氨苄西林，Bacampicillin通过抑制细菌细胞壁合成发挥杀菌作用[1-2]。Bacampicillin可用于敏感菌引起的呼吸道感染、泌尿系统感染和皮肤软组织感染等相关研究[3-4]。
在体外，Bacampicillin（0.2mM）孵育Caco-2细胞5-10min，Caco-2细胞对Bacampicillin的摄取率显著高于Ampicillin，Bacampicillin的跨膜转运在培养基pH值升高时显著增加[5]。
在体内，Bacampicillin（0-3mg/小鼠/天）口服处理常规雌性瑞士小鼠（从第3周开始持续4周），Bacampicillin的粪便菌群几乎未受影响，Bacampicillin对肠道正常保护性菌群的干扰远小于氨苄西林及其与克拉维酸的组合[6]。Bacampicillin（135mg/kg；单次）口服处理空腹SPF大鼠，Bacampicillin能使大鼠的血液、肾脏、肝脏以及皮下植入组织笼中的组织液获得更高浓度的氨苄西林峰值水平；在实验性小鼠感染模型中，在感染4小时后给药治疗流感嗜血杆菌感染时，口服给药Bacampicillin（135mg/kg），Bacampicillin显示出比氨苄西林更高的抗感染活性[7]。
| Cell experiment [1]: | |
Cell lines | Caco-2 cells (human intestinal epithelial cell line) |
Preparation Method | Caco-2 cells were maintained in Dulbecco's minimal essential medium (DMEM) supplemented with 10% heat-inactivated fetal bovine serum (FBS) at 37°C, 5% CO₂. Caco-2 cells were incubated in Bacampicillin (0.2mM) at 37°C for 5-10min. |
Reaction Conditions | 0.2mM; 5-10min. |
Applications | Bacampicillin was rapidly and extensively converted to its active metabolite ampicillin upon entry into Caco-2 cells. Bacampicillin uptake was significantly higher than ampicillin and pivampicillin. This uptake was mediated by a specialized, carrier-mediated transport system shared with thiamine, as evidenced by significant inhibition by thiamine, oxythiamine, amiloride, and procainamide, and trans-stimulation by preloading cells with thiamine. The uptake increased markedly with the elevation of extracellular pH from 5 to 7. Bacampicillin permeation across Caco-2 cell monolayers from the apical to the basolateral side was significantly inhibited by thiamine. |
| Animal experiment [2]: | |
Animal models | Mice (NMRI strain) |
Preparation Method | Mice were infected intraperitoneally with various bacterial strains (e.g., Haemophilus influenzae, Klebsiella pneumoniae) in a challenge dose that resulted in death of control animals within 24-96 hours. In most cases, 0.5ml of 5% hog gastric mucin was co-administered with the bacteria. Bacampicillin (135mg/kg) and sodium ampicillin, dissolved in distilled water, were administered orally immediately after infection or, in one H. influenzae series, 4 hours after infection. |
Dosage form | 135mg/kg; Oral; simultaneously with or after the infection. |
Applications | Orally administered Bacampicillin showed good activity against a range of gram-positive and gram-negative bacterial infections. When administered immediately after infection, Bacampicillin was as active as or more active than an equimolar dose of ampicillin against nine out of eleven tested organisms. In a delayed treatment model (4 hours post H. influenzae infection), Bacampicillin was relatively more effective than ampicillin, requiring significantly lower median curative doses to clear the established infection. |
References: | |
| Cas No. | 37661-08-8 | SDF | |
| 别名 | 盐酸巴氨西林 | ||
| 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.[H]Cl | ||
| 分子式 | C21H28ClN3O7S | 分子量 | 501.98 |
| 溶解度 | DMSO : ≥ 5.1 mg/mL (10.16 mM) | 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 | 1.9921 mL | 9.9606 mL | 19.9211 mL |
| 5 mM | 398.4 μL | 1.9921 mL | 3.9842 mL |
| 10 mM | 199.2 μL | 996.1 μL | 1.9921 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。
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- Purity: >98.00% Appearance: A solid
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