![Ampicillin Trihydrate [D-(-)-α-Aminobenzylpenicillin] 7177-48-2](/picture/img/Ampicillin Trihydrate [D-(-)-α-Aminobenzylpenicillin] Chemical Structure.png)
Ampicillin Trihydrate [D-(-)-α-Aminobenzylpenicillin] is a transpeptidase inhibitor used as a broad-spectrum beta-lactam antibiotic by preventing bacterial cell wall formation. It has activity against a variety of gram-positive and gram-negative bacteria.
Physicochemical Properties
| Molecular Formula | C16H25N3O7S |
| Molecular Weight | 403.45 |
| Exact Mass | 403.141 |
| Elemental Analysis | C, 47.63; H, 6.25; N, 10.42; O, 27.76; S, 7.95 |
| CAS # | 7177-48-2 |
| Related CAS # | Ampicillin;69-53-4;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); 7177-48-2 (trihydrate); |
| PubChem CID | 23565 |
| Appearance | White to light yellow solid powder. |
| Boiling Point | 683.9ºC at 760 mmHg |
| Melting Point | 208 °C (dec.)(lit.) |
| Flash Point | 367.4ºC |
| Index of Refraction | 265 ° (C=0.1, H2O) |
| LogP | 1.154 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 27 |
| Complexity | 562 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | S1C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C(=O)O[H])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 |
| InChi Key | RXDALBZNGVATNY-CWLIKTDRSA-N |
| InChi Code | InChI=1S/C16H19N3O4S.3H2O/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)3*1H2/t9-,10-,11+,14-/m1.../s1 |
| Chemical Name | (2S,5R,6R)-6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate |
| Synonyms | Amcill; Aminobenzyl Penicillin; KS-R1; KS R1; KSR1; Omnipen; Pentrexyl; 615-347-9; 7177-48-2; Ampicillin trihydrate; Aminobenzylpenicillin trihydrate; Principen; Penbritin; AMPICILLIN/AMPICILLIN TRIHYDRATE; HXQ6A1N7R6; Polycillin; Ukapen |
| 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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 | Bacterial cell wall synthesis; β-lactam | |
| ln Vitro |
In an 11-week-old pig, ampicillin trihydrate (D-(-)-α-Aminobenzylpenicillin trihydrate) is very effective in treating hemorrhagic enteritis[1]. Maximum concentrations of ampicillin trihydrate 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 ischemia-reperfusion brain damage is offered by ampicillin trihydrate. Ampicillin trihydrate increases GLT-1 expression while decreasing MMP activity. After global forebrain ischemia, pretreatment with ampicillin trihydrate dramatically lowers medial hippocampal cell death[3]. |
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| ln Vivo |
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| 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. |
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| 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 |
Ampicillin (200 mg/kg/day) and penicillin G sodium salt (6,000 U/kg or 20,000 U/kg) were dissolved in normal saline and administered intraperitoneally (i.p.) for 5 days. Forebrain ischemia was induced as described earlier 24 h after the last injection. To elucidate the molecular mechanism of ampicillin, dihydrokainic acid (DHK) (10 mg/kg), a GLT-1 inhibitor, was administrated i.p. 30 min before the onset of ischemia. In the control animals, saline was administered instead of ampicillin or penicillin G, at the same volume and time schedule.[3] Ampicillin was tested on a 11-week old pig suffering from hemorrhagic enteritis. The antibiotic was administered orally in gelatin capsules. An initial dose of 8 mg/ Kg body weight was followed by two, 4 mg/Kg doses at 4 hour intervals. Fecal samples were obtained from the above scouring pig before the administration of the antibiotic and 48 hours after the first dose, by that time the animal had recovered. A third fecal sample was obtained from a healthy pig in another litter as a control. Dilutions of 'the fecal samples ranging up to 10-8 were plated in E.M.B. agar medium containing 0, 0.1, 1.0, 2.5, 5.0 and 10.0 uG of Ampicillin per ml. of the medium. The plates were incubated at 37°C. for 48 hours and the typical E. coli were enumerated. Seven representative colonies of E. colti were isolated from each fecal sample and characterized biochemically following Kaufmann's (5) scheme. The cultures were also identified serologically by employing 0 and K antisera prepared against six well described E. coli serotypes (E145, E681, E68II, G7, E4 and E57), isolated from diseased swine (Sojka, 10, 11). Antibiotic sensitivity of all the isolates was tested by employing sensi-discs4 of chlortetracycline, oxytetracycline, 30 and 5 uG each, Bacitracin, penicillin, 10 I.U. each, and Ampicillin5, 10 uG. A few E. coli colonies which grew in E.M.B. media containing 5.0 and 10.0 uG of Ampicillin per ml. were tested for their susceptibility to 10.0 uG Ampicillin with sensitivity discs.[1] |
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| 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. |
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| 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. |
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| Additional Infomation |
Ampicillin trihydrate is an odorless white microcrystalline powder with a bitter taste. A 0.25% solution in water has a pH of 3.5 to 5.5. (NTP, 1992) Ampicillin trihydrate is a hydrate. It contains an ampicillin. Ampicillin Trihydrate is the trihydrate form of ampicillin, a broad-spectrum semisynthetic derivative of aminopenicillin. Ampicillin trihydrate 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. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~81 mg/mL ( ~200.76 mM ) Water : 2~4.55 mg/mL(~11.28 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4786 mL | 12.3931 mL | 24.7862 mL | |
| 5 mM | 0.4957 mL | 2.4786 mL | 4.9572 mL | |
| 10 mM | 0.2479 mL | 1.2393 mL | 2.4786 mL |