MedKoo Cat#: 317188 | Name: Ampicillin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ampicillin is an antibiotic used to prevent and treat a number of bacterial infections. This includes respiratory tract infections, urinary tract infections, meningitis, salmonella infections, 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. It is not useful for the treatment of viral infections. Ampicillin was developed in 1961. It is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system. Ampicillin is in the penicillin group of beta-lactam antibiotics and is part of the aminopenicillin family. It is roughly equivalent to amoxicillin in terms of activity. Ampicillin is able to penetrate Gram-positive and some Gram-negative bacteria. It differs from penicillin G, or benzylpenicillin, only by the presence of an amino group. That amino group helps the drug penetrate the outer membrane of Gram-negative bacteria. Ampicillin acts as an irreversible inhibitor of the enzyme transpeptidase, which is needed by bacteria to make their cell walls. It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis; therefore ampicillin is usually bacteriocidal.

Chemical Structure

Ampicillin
Ampicillin
CAS#69-53-4 (free acid)

Theoretical Analysis

MedKoo Cat#: 317188

Name: Ampicillin

CAS#: 69-53-4 (free acid)

Chemical Formula: C16H19N3O4S

Exact Mass: 349.1096

Molecular Weight: 349.40

Elemental Analysis: C, 55.00; H, 5.48; N, 12.03; O, 18.32; S, 9.18

Price and Availability

Size Price Availability Quantity
1g USD 150.00 Ready to ship
2g USD 250.00 Ready to ship
5g USD 450.00 Ready to ship
10g USD 650.00 Ready to ship
20g USD 950.00 2 weeks
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Synonym
Aminobenzylpenicillin; Ampicillin acid; Principen; Amcill; Ampicilline
IUPAC/Chemical Name
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChi Key
AVKUERGKIZMTKX-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H19N3O4S/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)
SMILES Code
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
Appearance
Solid powder
Purity
>96% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Certificate of Analysis
Safety Data Sheet (SDS)
Biological target:
Ampicillin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall.
In vitro activity:
To evaluate if the in vitro activity of ampicillin increases when combined with ceftriaxone. The activity of ampicillin and ceftriaxone was evaluated against six Listeria monocytogenes invasive clinical isolates. Ampicillin and ceftriaxone MICs were determined by the broth microdilution method. Synergy was evaluated by checkerboard and time-kill curves methods. All six L. monocytogenes strains were susceptible to ampicillin (MICs 0.25-0.5 mg/L). A bacteriostatic synergy was demonstrated by the FIC index of 0.5 and a 2.5 log10 CFU reduction on the six strains studied for MIC ampicillin plus 16 mg/L ceftriaxone concentrations. The association of ceftriaxone with ampicillin increases the in vitro activity of ampicillin, and therefore could be a valuable option in the treatment of invasive infection by L. monocytogenes. Reference: Lepe JA, Rodríguez-Villodres A, Martín-Gutiérrez G, Luque R, Aznar J. In vitro study of synergy of ampicillin with ceftriaxone against Listeria monocytogenes. Rev Esp Quimioter. 2019 Oct;32(5):465-468. Epub 2019 Sep 12. PMID: 31515975; PMCID: PMC6790883.
In vivo activity:
This study aimed to determine if amoxicillin disturbs the enamel mineralization in in vivo experiments. Fifteen pregnant rats were randomly assigned into three groups to received daily phosphatase-buffered saline or amoxicillin as either 100 or 500 mg/kg. Mice received treatment from day 13 of pregnancy to day 40 postnatal. After birth, the offsprings from each litter continued to receive the same treatment according to their respective group. Calcium (Ca) and phosphorus (P) content in the dental hard tissues were analyzed from 60 upper first molars and 60 upper incisors by the complexometric titration method and colorimetric analysis using a spectrophotometer at 680 nm, respectively. Lower incisors were analyzed by X-ray microtomography, it was measured the electron density of lingual and buccal enamel, and the enamel and dentin thickness. Differences in Ca and P content and electron density among the groups were analyzed by one-way ANOVA. There was no significant difference on enamel electron density and thickness among the groups (p > 0.05). However, in incisors, the higher dose of amoxicillin decreased markedly the electron density in some rats. There were no statistically significant differences in Ca (p = 0.180) or P content (p = 0.054), although the higher dose of amoxicillin could affect the enamel in some animals. The amoxicillin did not significantly alter the enamel mineralization and thickness in rats. Reference: Feltrin-Souza J, Jeremias F, Alaluusua S, Sahlberg C, Santos-Pinto L, Jernvall J, Sova S, Cordeiro RCL, Cerri PS. The effect of amoxicillin on dental enamel development in vivo. Braz Oral Res. 2020 Sep 4;34:e116. doi: 10.1590/1807-3107bor-2020.vol34.0116. PMID: 32901731.

Preparing Stock Solutions

The following data is based on the product molecular weight 349.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Lepe JA, Rodríguez-Villodres A, Martín-Gutiérrez G, Luque R, Aznar J. In vitro study of synergy of ampicillin with ceftriaxone against Listeria monocytogenes. Rev Esp Quimioter. 2019 Oct;32(5):465-468. Epub 2019 Sep 12. PMID: 31515975; PMCID: PMC6790883.
In vitro protocol:
Lepe JA, Rodríguez-Villodres A, Martín-Gutiérrez G, Luque R, Aznar J. In vitro study of synergy of ampicillin with ceftriaxone against Listeria monocytogenes. Rev Esp Quimioter. 2019 Oct;32(5):465-468. Epub 2019 Sep 12. PMID: 31515975; PMCID: PMC6790883.
In vivo protocol:
Feltrin-Souza J, Jeremias F, Alaluusua S, Sahlberg C, Santos-Pinto L, Jernvall J, Sova S, Cordeiro RCL, Cerri PS. The effect of amoxicillin on dental enamel development in vivo. Braz Oral Res. 2020 Sep 4;34:e116. doi: 10.1590/1807-3107bor-2020.vol34.0116. PMID: 32901731.
1: Belhaj M, Boutiba-Ben Boubaker I, Slim A. Penicillin-Binding Protein 5 Sequence Alteration and Levels of plp5 mRNA Expression in Clinical Isolates of Enterococcus faecium with Different Levels of Ampicillin Resistance. Microb Drug Resist. 2015 Nov 30. [Epub ahead of print] PubMed PMID: 26618475. 2: Wang P, Pang S, Zhang H, Fan M, He L. Characterization of Lactococcus lactis response to ampicillin and ciprofloxacin using surface-enhanced Raman spectroscopy. Anal Bioanal Chem. 2015 Nov 27. [Epub ahead of print] PubMed PMID: 26613795. 3: Yokoyama Y, Matsumoto K, Ikawa K, Watanabe E, Yamamoto H, Imoto Y, Morikawa N, Takeda Y. Pharmacokinetics of Prophylactic Ampicillin-Sulbactam and Dosing Optimization in Patients Undergoing Cardiovascular Surgery with Cardiopulmonary Bypass. Biol Pharm Bull. 2015;38(11):1817-21. doi: 10.1248/bpb.b15-00334. PubMed PMID: 26521833. 4: Gar Alalm M, Ookawara S, Fukushi D, Sato A, Tawfik A. Improved WO3 photocatalytic efficiency using ZrO2 and Ru for the degradation of carbofuran and ampicillin. J Hazard Mater. 2016 Jan 25;302:225-31. doi: 10.1016/j.jhazmat.2015.10.002. Epub 2015 Oct 22. PubMed PMID: 26476309. 5: Parker SL, Adnan S, Ordóñez Meija JL, Paterson DL, Lipman J, Roberts JA, Wallis SC. An UHPLC-MS/MS method for the simultaneous determination of ampicillin and sulbactam in human plasma and urine. Bioanalysis. 2015 Sep 23. [Epub ahead of print] PubMed PMID: 26395242. 6: Kussmann M, Schuster L, Zeitlinger M, Pichler P, Reznicek G, Wiesholzer M, Burgmann H, Poeppl W. The influence of different peritoneal dialysis fluids on the in vitro activity of ampicillin, daptomycin, and linezolid against Enterococcus faecalis. Eur J Clin Microbiol Infect Dis. 2015 Nov;34(11):2257-63. doi: 10.1007/s10096-015-2477-8. Epub 2015 Sep 4. PubMed PMID: 26337433. 7: Sánchez-Díaz AM, Cuartero C, Rodríguez JD, Lozano S, Alonso JM, Rodríguez-Domínguez M, Tedim AP, Del Campo R, López J, Cantón R, Ruiz-Garbajosa P. The rise of ampicillin-resistant Enterococcus faecium high-risk clones as a frequent intestinal colonizer in oncohaematological neutropenic patients on levofloxacin prophylaxis: a risk for bacteraemia? Clin Microbiol Infect. 2015 Aug 29. pii: S1198-743X(15)00794-6. doi: 10.1016/j.cmi.2015.08.008. [Epub ahead of print] PubMed PMID: 26321668. 8: Lâm TT, Claus H, Elias J, Frosch M, Vogel U. Ampicillin resistance of invasive Haemophilus influenzae isolates in Germany 2009-2012. Int J Med Microbiol. 2015 Oct;305(7):748-55. doi: 10.1016/j.ijmm.2015.08.028. Epub 2015 Aug 21. PubMed PMID: 26321008. 9: Sun L, Jia L, Xie X, Xie K, Wang J, Liu J, Cui L, Zhang G, Dai G, Wang J. Quantitative analysis of amoxicillin, its major metabolites and ampicillin in eggs by liquid chromatography combined with electrospray ionization tandem mass spectrometry. Food Chem. 2016 Feb 1;192:313-8. doi: 10.1016/j.foodchem.2015.07.028. Epub 2015 Jul 8. PubMed PMID: 26304353. 10: Jaspers S, Verbeke G, Böhning D, Aerts M. Application of the Vertex Exchange Method to estimate a semi-parametric mixture model for the MIC density of Escherichia coli isolates tested for susceptibility against ampicillin. Biostatistics. 2015 Aug 13. pii: kxv030. [Epub ahead of print] PubMed PMID: 26272992.