Bacampicillin |
Catalog No.GC33966
One-Click Copy Product Info
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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.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 50972-17-3
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.
| 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. | 50972-17-3 | SDF | |
| 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 | ||
| Formula | C21H27N3O7S | M.Wt | 465.52 |
| Solubility | Soluble in DMSO | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.1481 mL | 10.7407 mL | 21.4814 mL |
| 5 mM | 429.6 μL | 2.1481 mL | 4.2963 mL |
| 10 mM | 214.8 μL | 1.0741 mL | 2.1481 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 38 reference(s) in Google Scholar.)