Ampicillin sodium is a potent broad-spectrum beta-lactam antibiotic widely used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously. Like all antibiotics, it is not useful for the treatment of viral infections.
Physicochemical Properties
| Molecular Formula | C16H18N3NAO4S |
| Molecular Weight | 371.3866 |
| Exact Mass | 371.091 |
| Elemental Analysis | C, 51.75; H, 4.89; N, 11.31; Na, 6.19; O, 17.23; S, 8.63 |
| CAS # | 69-52-3 |
| 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) |
| PubChem CID | 23663979 |
| Appearance | White to off-white solid powder |
| Boiling Point | 683.9ºC at 760 mmHg |
| Melting Point | 215 °C (dec.)(lit.) |
| LogP | 0.012 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 25 |
| Complexity | 568 |
| Defined Atom Stereocenter Count | 4 |
| 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+] |
| InChi Key | KLOHDWPABZXLGI-YWUHCJSESA-M |
| 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 |
| 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*)))- |
| 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 |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets | β-lactam; cell wall synthesis |
| 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]. |
| 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]. |
| 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. |
| 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] |
| 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]. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Substantial information indicates that ampicillin produces low levels in milk that are not expected to cause adverse effects in breastfed infants. Occasionally disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush have been reported with penicillins, but these effects have not been adequately evaluated. Ampicillin is acceptable in nursing mothers. ◉ Effects in Breastfed Infants An uncontrolled observation of the breastfed infants of mothers taking ampicillin noted a seeming increase in cases of diarrhea and candidiasis that was attributed to ampicillin in breastmilk. In a prospective follow-up study, 5 nursing mothers reported taking ampicillin (dosage unspecified). One mother reported diarrhea in her infant. No rashes or candidiasis were reported among the exposed infants. A small, controlled, prospective study had mothers monitor their infants for signs of adverse effects (furring of the tongue, feeding difficulties, changes in stool frequency and consistency, diaper rash, and skin rash). Weight change and the development of jaundice were also recorded. No statistical differences in these parameters were found between the infants of the control mothers and those of mothers taking ampicillin. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
[1]. Effect of Ampicillin on E. Coli of Swine Origin. Can J Comp Med Vet Sci. 1963 Sep;27(9):223-7. [2]. Ampicillin in portal and peripheral blood and bile after oral administration of ampicillin andpivampicillin. Eur J Clin Pharmacol. 1974;7(2):133-5. [3]. The neuroprotective mechanism of ampicillin in a mouse model of transient forebrain ischemia. Korean J Physiol Pharmacol. 2016 Mar;20(2):185-92. |
| Additional Infomation |
Ampicillin sodium is an organic sodium salt. It contains an ampicillin(1-). Ampicillin Sodium is the sodium salt form of ampicillin, a broad-spectrum semisynthetic derivative of aminopenicillin. Ampicillin sodium inhibits bacterial cell wall synthesis by binding to penicillin binding proteins, thereby inhibiting peptidoglycan synthesis, a critical component of the bacterial cell wall. Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. See also: Ampicillin (has active moiety); Ampicillin sodium; sulbactam sodium (component of). |
Solubility Data
| Solubility (In Vitro) |
H2O : ≥ 200 mg/mL (~538.53 mM) DMSO : ~200 mg/mL (~538.53 mM) |
| 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. 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. 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 corn oil and mix evenly. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| 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 |