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| Targets |
β-lactam; cell wall synthesis
Ampicillin sodium targets penicillin-binding proteins (PBPs), which are transpeptidases essential for the final stages of bacterial cell wall synthesis. By binding to and inhibiting these PBPs, it prevents the cross-linking of peptidoglycan chains, a critical component of the bacterial cell wall. This weakens the cell wall, leading to osmotic instability and ultimately bacterial cell lysis and death. It is a β-lactam antibiotic and is inactivated by β-lactamases (lactamases), enzymes produced by some bacteria that confer resistance. |
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| ln Vitro |
Ampicillin has a dose-dependent effect on swine-derived E. Coli growth inhibition. Ampicillin's effective inhibitory concentration was 2.5 uG/mL[1].
In vitro, Ampicillin sodium demonstrates broad-spectrum bactericidal activity. It is effective against a wide range of bacteria, including both Gram-positive and Gram-negative organisms. Its activity is typically determined by measuring the minimum inhibitory concentration (MIC) against various bacterial strains. It is commonly used in cell culture media as a selective agent to maintain plasmids that carry an ampicillin resistance gene (bla). In such applications, it prevents the growth of non-transformed cells while allowing the growth of cells that have taken up the plasmid and express the β-lactamase enzyme. |
| ln Vivo |
Ampicillin is very effective in alleviating the symptoms of hemorrhagic enteritis in a 11-week old pig[1]. Maximum concentrations of ampicillin are twice as high in bile as they are in serum. After an oral dosage, the peak concentration of ampicillin in portal blood is twice as high as in peripheral blood[2]. Neuroprotection against brain damage caused by ischemia-reperfusion is offered by ampicillin. Ampicillin raises the level of GLT-1 expression while decreasing MMP activity. After global forebrain ischemia, pretreatment with ampicillin dramatically lowers medial hippocampal cell death[3].
In vivo, Ampicillin sodium is used to treat infections caused by susceptible bacteria. It is effective against a range of pathogens and is used for conditions such as respiratory tract infections, urinary tract infections, and meningitis. It is also used prophylactically to prevent group B streptococcal infection in newborns. Its clinical use is limited by the development of bacterial resistance, primarily through the production of β-lactamases that inactivate the drug. In animal models, it is used to study bacterial infections and to evaluate the efficacy of new antibacterial agents. |
| Enzyme Assay |
SENSITIVITY TESTING[1]
A set of 5 replicate tubes at each concentration of the antibiotic were inoculated with one drop each of an 18 hour growth of the test culture. The inoculated tubes were incubated at 37°C. for 6 hours, after which further growth was stopped by mixing formalin at 0.5% final concentration. Growth of cultures was recorded as the optical density, employing a Fisher Electrophotometer3 with a 525 m.u. filter.
In vitro non-cell enzyme/receptor binding assays for Ampicillin sodium are not common, as it is an antibiotic that targets a cellular process (cell wall synthesis) rather than a specific enzyme in a cell-free system. However, its mechanism can be studied by measuring its ability to inhibit the transpeptidase activity of PBPs in membrane preparations. This involves incubating the compound with isolated PBPs and a labeled substrate, then measuring the extent of cross-linking. The results are typically expressed as the concentration required to inhibit 50% of the enzyme activity (IC₅₀). |
| Cell Assay |
The in vitro susceptibility of 103 cultures of E. coli isolated from scouring and nonscouring pigs, and four cultures of Salmonella isolated from a case of necrotic enteritis was tested against Ampicillin contained in nutrient broth at concentrations of 0, 0.1, 1.0 and 5.0 uG per ml. of the medium. All but three cultures of E. coli were found to be susceptible to 5.0 uG/ml., all Salmonella isolates were also susceptible to this concentration of the antibiotic. Susceptibility of E. coli was also tested by plating dilutions of fecal samples obtained from either a scouring or a nonscouring pig, with E.M.B. agar containing 0, 0.1, 1.0, 2.5, 5.0 and 10.0 uG Ampicillin per ml. of the medium. No difference in the growth of E. coli was observed at 0, 0.1 and 1.0 uG concentrations. The three higher concentrations of the antibiotic inhibited the growth of E. coli proportional to the amount of Ampicillin in each concentration. Ampicillin proved very effective in alleviating the symptoms of hemorrhagic enteritis in a 11-week old pig. The disappearance of scours was associated with the replacement of the previously existing sero-biotypes of fecal E. coliwith another aberrant type of E.coli which produced H2S. No Ampicillin resistant strains of E. coli emerged following treatment of the animal with this antibiotic.[1]
In vitro cell-based assays for Ampicillin sodium are standard microbiological assays used to determine its antimicrobial activity. These include broth microdilution and agar diffusion methods to determine the minimum inhibitory concentration (MIC) against various bacterial strains. The compound is tested against a panel of organisms to define its spectrum of activity. Time-kill assays are also used to assess the bactericidal activity over time. The compound's effectiveness can be evaluated in the presence of β-lactamase to assess its stability. |
| Animal Protocol |
Mice: Normal saline is used to dissolve ampicillin. After receiving halothane anesthesia, male C57BL/6 mice had their common carotid arteries blocked bilaterally for 40 minutes. Penicillin G (6,000 U/kg or 20,000 U/kg, intraperitoneally [i.p.]) or ampicillin (200 mg/kg) was given intraperitoneally (i.p.) every day for five days prior to transient forebrain ischemia. The same volume and timing of saline administration were used for the control animals[3].
In vivo animal studies for Ampicillin sodium are conducted to evaluate its efficacy in treating bacterial infections. Animal models of infection, such as murine sepsis or pneumonia models, are used. The compound is administered via various routes (e.g., subcutaneous, intramuscular, intravenous), and the reduction in bacterial load, survival rates, or clinical signs of infection are measured. Pharmacokinetic studies are also performed to determine its absorption, distribution, metabolism, and excretion (ADME) in the animal model. |
| ADME/Pharmacokinetics |
Ampicillin sodium has a molecular weight of 371.39 g/mol and a molecular formula of C₁₆H₁₈N₃NaO₄S. It is a white to off-white solid powder. It is hygroscopic and should be stored at +2°C to +8°C. It is soluble in water, and aqueous stock solutions are stable for up to 1 month at -20°C. The product is heat-resistant and stable between pH 2 and 11. It has a half-life of approximately 1 hour and is primarily excreted unchanged in the urine.
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of Use During Lactation A large body of information indicates that the concentration of ampicillin in breast milk is low and is not expected to have adverse effects on breastfed infants. Although there are reports of penicillin-type drugs occasionally disrupting the infant's gut microbiota, leading to diarrhea or thrush, these effects have not been fully assessed. Ampicillin is safe for breastfeeding women. ◉ Effects on Breastfed Infants A non-controlled observational study of infants breastfed by mothers who had taken ampicillin found an apparent increase in cases of diarrhea and candidiasis, which was thought to be due to ampicillin in breast milk. In a prospective follow-up study, five breastfeeding mothers reported taking ampicillin (dosage not specified). One mother reported that her infant developed diarrhea. No rashes or candidiasis were reported in the exposed infants. A small, controlled, prospective study required mothers to monitor their infants for signs of adverse reactions (thickened tongue coating, feeding difficulties, changes in stool frequency and consistency, diaper rash, and skin rash). Weight changes and the occurrence of jaundice were also recorded. No statistically significant differences were found in these parameters between infants of control mothers and infants of mothers taking ampicillin. ◉ Effects on breastfeeding and breast milk As of the revision date, no relevant published information was found. Ampicillin sodium is generally well-tolerated, but can cause side effects such as gastrointestinal disturbances, skin rashes, and, rarely, anaphylaxis. It is classified as an irritant. It is contraindicated in patients with a history of penicillin allergy. Its use can lead to the development of antibiotic resistance. As a research compound, it is intended for laboratory use and should be handled with appropriate safety precautions. |
| References | |
| Additional Infomation |
Ampicillin sodium is an organocalocyanate containing an ampicillin (1-) group. Ampicillin sodium is the sodium salt form of ampicillin, a broad-spectrum semi-synthetic aminopenicillin derivative. Ampicillin sodium inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins, thereby inhibiting peptidoglycan synthesis, a key component of the bacterial cell wall. Ampicillin sodium is a semi-synthetic penicillin derivative and can be used as an orally effective broad-spectrum antibiotic. See also: ampicillin (containing the active portion); ampicillin sodium; sulbactam sodium (one of the components).
Ampicillin sodium is a broad-spectrum β-lactam antibiotic widely used in both clinical and research settings. It inhibits bacterial cell wall synthesis by targeting penicillin-binding proteins. It is commonly used as a selective agent for ampicillin-resistant plasmids in molecular biology. It is also known as D-(-)-6-(2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt. It is available in various grades, including cell culture grade. |
| Molecular Formula |
C16H18N3NAO4S
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|---|---|
| Molecular Weight |
371.3866
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| Exact Mass |
371.091
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| Elemental Analysis |
C, 51.75; H, 4.89; N, 11.31; Na, 6.19; O, 17.23; S, 8.63
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| CAS # |
69-52-3
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| Related CAS # |
Ampicillin;69-53-4;Ampicillin trihydrate;7177-48-2; Ampicillin sodium;69-52-3; 69-53-4 (free acid); 23277-71-6 (potassium); 114977-84-3 (trimer trisodium) ; 69-52-3 (sodium); 7490-86-0 (hemisulfate); 33276-75-4 (benzathine); 119229-01-5 (embonate); 40688-84-4 (HCl)
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| PubChem CID |
23663979
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| Appearance |
White to off-white solid powder
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| Boiling Point |
683.9ºC at 760 mmHg
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| Melting Point |
215 °C (dec.)(lit.)
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| LogP |
0.012
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
25
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| Complexity |
568
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| Defined Atom Stereocenter Count |
4
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| SMILES |
S1C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C(=O)[O-])N2C([C@]([H])([C@@]12[H])N([H])C([C@@]([H])(C1C([H])=C([H])C([H])=C([H])C=1[H])N([H])[H])=O)=O.[Na+]
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| InChi Key |
KLOHDWPABZXLGI-YWUHCJSESA-M
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| InChi Code |
1S/C16H19N3O4S.Na/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1
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| Chemical Name |
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, (2S-(2alpha,5alpha,6beta(S*)))-
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| Synonyms |
Alpen-N; Amcill-S; Ampicillin natrium; 200-708-1; 69-52-3; Ampicillin sodium; Ampicillin sodium salt; Sodium ampicillin; Ampicillin natrium; Ampicillin (sodium); Citteral; Ampicillin sodium
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ≥ 200 mg/mL (~538.53 mM)
DMSO : ~200 mg/mL (~538.53 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (13.46 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (13.46 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 5 mg/mL (13.46 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: ≥ 2.5 mg/mL (6.73 mM) (saturation unknown) in 5% DMSO + 40% PEG300 + 5% Tween80 + 50% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 5: ≥ 2.5 mg/mL (6.73 mM) (saturation unknown) in 5% DMSO + 95% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 6: 50 mg/mL (134.63 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6926 mL | 13.4629 mL | 26.9259 mL | |
| 5 mM | 0.5385 mL | 2.6926 mL | 5.3852 mL | |
| 10 mM | 0.2693 mL | 1.3463 mL | 2.6926 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution 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 stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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