WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 317188
Description: 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.
MedKoo Cat#: 317188
Chemical Formula: C16H19N3O4S
Exact Mass: 349.10963
Molecular Weight: 349.4
Elemental Analysis: C, 55.00; H, 5.48; N, 12.03; O, 18.32; S, 9.18
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: >98% (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
The following data is based on the product molecular weight 349.4 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.
|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|
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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.
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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.