Ampicillin sodium (Domicillin), a widely used antibiotic in the medical field, belongs to the beta-lactam class of drugs, specifically the penicillin subgroup. It is a derivative of ampicillin, combined with sodium ions to enhance its solubility and stability. This antibiotic is primarily effective against a broad spectrum of Gram-positive and some Gram-negative bateria, making it a versatile treatment option for various infections.The mechanism of action involves inhibiting the baterial cell wall synthesis by binding to specific penicillin-binding proteins (PBPs). This binding disrupts the formation of the peptidoglycan layer, essential for baterial cell structure and integrity, ultimately leading to cell lysis and baterial death.
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| Chemical Formula | C16H18N3NaO4S |
| Exact Mass | 371.09 |
| Molecular Weight | 371.39 |
| m/z | 371.09 (100.0%), 372.09 (17.3%), 373.09 (4.5%), 373.10 (1.4%), 372.09 (1.1%) |
| Elemental Analysis | C, 51.75; H, 4.89; N, 11.31; Na, 6.19; O, 17.23; S, 8.63 |
Ampicillin sodium, as a classic broad-spectrum semi synthetic penicillin antibiotic, has become an important drug in the treatment of infectious diseases since it came out in the 1960s with its unique antibacterial mechanism and extensive clinical application value. It exerts bactericidal effects by inhibiting baterial cell wall synthesis and has significant activity against both Gram positive and some Gram negative bateria.
Antibacterial mechanism: precise targeting of cell wall synthesis
The core mechanism of its antibaterial activity is to inhibit the key enzyme involved in baterial cell wall synthesis, transpeptidase. The baterial cell wall is composed of peptidoglycan, which undergoes three stages of synthesis: intracellular synthesis, transmembrane transport, and extracellular cross-linking. It binds to penicillin binding proteins (PBPs) to block the formation of cross-linking between peptidoglycan chains catalyzed by transpeptidase, leading to structural defects in the cell wall. Under osmotic pressure, bateria expand and lyse due to the inability to maintain cell wall integrity, ultimately leading to death.
This mechanism enables it to have a strong bactericidal effect on bateria in the growth and reproduction stage, while having a weaker effect on bateria in the dormant stage.
It is worth noting that the β - lactam ring structure of this substance is easily hydrolyzed and inactivated by β - lactamase produced by bateria, thus reducing its sensitivity to enzyme producing strains. Clinically, the antibaterial spectrum is often expanded by combining β - lactase inhibitors (such as sulbactam) or selecting enzyme resistant penicillins (such as benzylpenicillin).
Indications: Broad spectrum application covering multiple systemic infections
Antibacterial spectrum covers gram-positive bateria (such as hemolytic streptococcus, pneumonia streptococcus, non enzyme producing staphylococcus) and some gram-negative bateria (such as Haemophilus influenzae, Escherichia coli, Proteus mirabilis, Salmonella, Shigella), which are clinically applicable to the following infectious diseases:
1. Respiratory tract infection
Upper respiratory tract: It is effective in treating pharyngitis, tonsillitis, otitis media, etc., especially for streptococcal infections.
For example, acute tonsillitis caused by Group A β - hemolytic streptococcus can shorten the course of the disease and reduce the risk of complications such as rheumatic fever and glomerulonephritis by inhibiting baterial growth.
Lower respiratory tract: Used for the treatment of bronchitis and pneumonia, especially effective against Streptococcus pneumoniae and Haemophilus influenzae infections. Research has shown that the combination of ampicillin sodium and macrolide antibiotics can cover atypical pathogens such as mycoplasma and chlamydia, and improve the cure rate of community-acquired pneumonia.
2. Urinary system infection
It is a commonly used medication for cystitis and pyelonephritis, especially sensitive to common pathogens such as Escherichia coli and Proteus. Its urine concentration is high (up to 10-100 times the blood drug concentration), and it has strong stability in acidic urine, making it suitable for mild to moderate urinary tract infections.
For complex urinary tract infections (such as concomitant stones and obstruction), combination therapy with aminoglycosides or third-generation cephalosporins is necessary to enhance efficacy.
3. Gastrointestinal infection
Enteritis, typhoid fever, and paratyphoid fever caused by Salmonella and Shigella are classic indications for product.
For example, when treating Salmonella typhi infection, the risk of complications such as intestinal bleeding and perforation can be reduced by inhibiting baterial growth. In addition, it has a certain therapeutic effect on severe diarrhea caused by Vibrio cholerae, but attention should be paid to supplementing electrolytes to correct dehydration.
4. Skin and soft tissue infections
Skin infections such as boils, cellulitis, and erysipelas caused by Staphylococcus aureus and Streptococcus pyogenes can be effectively concentrated through local infiltration. For mild infections, oral administration is sufficient; Severe or deep infections require intravenous administration, combined with topical antibiotics (such as mupirocin) to enhance efficacy.
5. Blood flow infection and central nervous system infection
Sepsis: It can be used for bloodstream infections caused by sensitive bateria, especially for infections of the Enterococcus genus (such as Enterococcus faecalis and Enterococcus faecalis), and is often used as the preferred drug for Enterococcus sepsis.
Meningitis: For meningitis caused by Haemophilus influenzae and Streptococcus pneumoniae, it can be treated through the blood-brain barrier (cerebrospinal fluid concentration can reach 30% -50% of blood drug concentration), but it needs to be combined with third-generation cephalosporins (such as ceftriaxone) to cover drug-resistant strains.
6. Other infections
Endocarditis: In the case of endocarditis caused by Streptococcus pyogenes, the combination of aminoglycosides (such as gentamicin) can increase baterial clearance and reduce the risk of recurrence.
Biliary tract infection: It has a high concentration in bile and can be used for the treatment of cholecystitis and cholangitis, especially for infections caused by Escherichia coli and Klebsiella.
Reproductive system infection: Urethritis and cervicitis caused by Neisseria gonorrhoeae (non enzyme producing strain), ampicillin sodium can be used as an alternative treatment drug, but attention should be paid to drug resistance issues.
Due to its broad antibacterial spectrum, it is commonly used in the treatment of various infections caused by sensitive bateria, including respiratory infections, gastrointestinal infections, urinary tract infections, soft tissue infections, endocarditis, meningitis, and sepsis. It can also be used for mixed infections caused by Streptococcus pyogenes or Streptococcus pneumoniae and penicillin-resistant Staphylococcus aureus.
Role in Cell Culture
Prevention of Bacterial Contamination
Domicillin is one of the most commonly used broad-spectrum antibacterial additives in routine cell culture systems. It is primarily applied to prevent exogenous contamination caused by susceptible Gram-positive and Gram-negative bacteria, which are easily introduced through culture media, operation procedures, or environmental exposure. By interfering with bacterial cell wall synthesis, domicillin creates a bacteria-inhibiting culture environment that effectively suppresses bacterial proliferation. It greatly reduces the risk of microbial infection and cross-contamination, providing a sterile and stable growth condition for cultured mammalian cells and microbial cell lines.
Maintenance of Cell Health
By continuously inhibiting bacterial growth and eliminating potential bacterial interference in the culture system, domicillin effectively maintains the normal physiological state, health and high viability of cultured cells. Uncontrolled bacterial contamination often leads to acidification of culture medium, production of harmful metabolites, and cell apoptosis, which seriously affects experimental results. The addition of domicillin stabilizes the culture microenvironment and ensures the smooth progress of cell proliferation, differentiation, passage and other key biological processes, improving the accuracy and reproducibility of cell culture experiments.
Usage Instructions
Concentration
Typically prepared as a stock solution (e.g., 100 mg/ml) and then diluted to the desired working concentration before being added to the cell culture medium.
Dilution and Addition
The stock solution is usually diluted 1:1000 with the cell culture medium, resulting in a final concentration that is effective against bateria but not harmful to the cells.
Frequency of Addition
The frequency of adding the item to the cell culture medium depends on the specific conditions and the type of cells being cultured. It is generally added at the beginning of the culture period and may be replenished as needed.
It is compatible with various cell culture media, including those containing serum or other growth factors. However, it is important to check for any potential interactions or incompatibilities before use.
Raw Material Preparation
The core starting material is 6-aminopenicillanic acid (6-APA), the parent nucleus of penicillin antibiotics. D-phenylglycine methyl ester hydrochloride acts as the side-chain acylating agent.
Auxiliary materials include triethylamine as an acid-binding agent, dichloromethane as an organic solvent, isooctanoic acid sodium salt for salt formation, and purified water for washing.
All raw materials meet pharmaceutical grade standards with strict control over heavy metals and microbial impurities. 6-APA is dried to remove residual moisture to prevent hydrolysis during acylation, while D-phenylglycine methyl ester is filtered to eliminate insoluble polymer impurities to guarantee high reaction conversion.
Acylation Condensation Core Reaction
The key step is the acylation between 6-APA and activated D-phenylglycine derivative under low temperature. Dissolve 6-APA in mixed dichloromethane-water solvent, add triethylamine to adjust pH to 6.5–7.2 to dissolve the penicillin nucleus completely.
Slowly drip activated D-phenylglycine methyl ester solution under stirring, and control reaction temperature at 0–5 °C. Low temperature suppresses β-lactam ring cleavage, which would cause product inactivation.
The reaction lasts 2–3 hours; HPLC monitors residual 6-APA content to confirm full condensation and form ampicillin methyl ester intermediate. Excessive side-chain raw material is removed by dilute alkali washing to avoid subsequent color deepening.
Hydrolysis and Acid Precipitation of Ampicillin
Add dilute sodium hydroxide solution dropwise to the organic phase containing ampicillin methyl ester to conduct mild ester hydrolysis at 5–10 °C, converting methyl ester to free ampicillin.
After hydrolysis, separate the water layer, adjust pH to 3.8–4.2 with dilute hydrochloric acid, and free ampicillin solid precipitates out.
Filter the crude ampicillin solid, wash with cold purified water repeatedly to remove residual chloride ions and organic solvent residues, then vacuum dry at low temperature to obtain high-purity ampicillin solid with purity over 99.0%.
Salt Formation and Crystallization
Dissolve purified ampicillin in mixed solvent of isopropanol and water, add sodium isooctanoate solution dropwise under stirring to carry out salt-forming reaction at 10–15 °C.
Ampicillin sodium gradually separates as crystalline powder. Cool the system to 0 °C for full crystal precipitation, filter and rinse the crystals with cold isopropanol to reduce solubility loss.
Vacuum drying under 40 °C removes residual solvent, then sieve and package the finished domicillin powder. The whole process strictly avoids high temperature and strong acid/alkali to protect the unstable β-lactam ring, ensuring high potency and low polymer impurities compliant with pharmacopoeia standards.
Natural penicillin only targets Gram-positive bacteria and exhibits poor efficacy against Gram-negative infections, limiting its clinical application. In the late 1950s, researchers at Britain's Beecham Research Laboratories realized structural modification based on the 6-APA penicillin nucleus.
By introducing an aminophenyl side chain, they successfully synthesized ampicillin in 1958, which possessed a broad antibacterial spectrum against both Gram-positive and Gram-negative bacteria.
This sodium salt derivative retains stable antibacterial activity and achieves good water solubility, making it suitable for clinical injection administration.
It was officially launched in 1961 and approved by the US FDA in 1963 as a classic injectable broad-spectrum semi-synthetic penicillin.
Due to its reliable safety and bactericidal performance, domicillin was widely promoted worldwide for treating respiratory, urinary and systemic bacterial infections. China realized its localized mass production in the 1970s. To date, it remains a fundamental and commonly used antibiotic in modern clinical anti-infection treatment.
faq
What is ampicillin sodium used for?
Ampicillin is a medication used to manage and treat certain bacterial infections. It is in the penicillin class of medications. Ampicillin was developed to overcome the issue of drug resistance and extend the antimicrobial coverage of penicillins.
What is the use of ampicillin sodium salt?
Ampicillin can be used in cell culture applications. Ampicillin Sodium Salt is in powder form which makes it an economical choice that can be used in a wide range of gram-positive and gram-negative infections.
Does ampicillin cause hypernatremia?
To the best of our knowledge, there are no documented cases of hypernatremia resulting from the use of ampicillin/sulbactam. We present the case of a 58-year-old male who developed this electrolyte imbalance during hospitalization, which was refractory to conventional management.
What is the difference between ampicillin and ampicillin sodium?
Ampicillin sodium salt is a semi-synthetic derivative of penicillin used to select for ampicillin resistance in mutated and transformed cells. Ampicillin is a ß-lactam antibiotic that inhibits bacterial cell wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane.
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