University of North Florida
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Stuart Chalk, Ph.D.
Department of Chemistry
University of North Florida
Phone: 1-904-620-1938
Fax: 1-904-620-3535
Email: schalk@unf.edu
Website: @unf

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Ampicillin

  • IUPAC 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
  • Molecular Formula: C16H19N3O4S
  • CAS Registry Number: 69-53-4
  • InChI: 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)/t9-,10-,11+,14-/m1/s1
  • InChI Key: AVKUERGKIZMTKX-NJBDSQKTSA-N

@ ChemSpider@ NIST@ PubChem

Citations 6

"Simultaneous Determination Of Penicillin And Ampicillin By Spectral Fiberoptic Enzyme Optodes And Multivariate Data-analysis Based On Transient Signals Obtained By Flow Injection Analysis"
Talanta 1995 Volume 42, Issue 12 Pages 2065-2072
Jürgen Polster*, Gertraud Prestel, Markus Wollenweber, Gerolf Kraus and Günter Gauglitz

Abstract: A multicomponent detection system using optical biosensors and flow injection analysis is described. The analysis of mixtures containing penicillin and ampicillin was realised by evaluating dynamic measurements of Phenol Red spectra in penicillinase optodes in combination with a diode array spectrometer. A variety of optodes has been produced by changing the composition of the receptor gel and the working pH. A set of characteristic quantities (describing dynamic and static features) could be obtained for each optode. These were used to compare the predictivity of classical multivariate calibration methods as well as of an artificial neural network, In addition, different algorithms were applied for the evaluation of the spectral data in order to select the most appropriate method for feature extraction. In consequence, the information obtained from the multivariate calibration models was used to set up an optimal sensor array consisting of four optodes with different types of penicillinase at different working pH. (25 references)
Sensor Sensor Calibration Multivariate calibration Optosensing Neural network Optical fiber

"Derivatization Techniques For High Performance Liquid Chromatographic Analysis Of β-lactams"
J. Chromatogr. A 1984 Volume 297, Issue 1 Pages 385-391
M. E. Rogers, M. W. Adlard, G. Saunders and G. Holt

Abstract: Antibiotic β-lactams with a C6 side-chain [e.g., penicillin X(I) and benzylpenicillin(II)] were pre-derivatized with imidazole and a salt of Ni(II), Zn(II), Ag+, Cd(II), Au+ or Hg(II) (HgCl2 best) before analysis by HPLC on a column (20 cm x 4.6 mm) of Spherisorb C18 (5 µm) with aqueous 0.01 M NaH2PO4 buffer (pH 6.5) - acetonitrile (4:1), 0.01 M in complexing agent (EDTA, NaCN or Na2S2O3), as mobile phase (1.5 mL min-1) and detection at 325 nm. Although NaCN was the best complexing agent, the less toxic ones were preferred. With use of EDTA and HgCl2 calibration graphs based on peak area were rectilinear for up to 50 µg mL-1 of I and II; for determination of 25 µg mL-1 of I, the coefficient of variation was 2% (n = 10). With Na2S2O3, the detection limits were 0.5 µg mL-1 for I and II. β-Lactams with a primary amino-group, e.g., 6-aminopenicillanic acid(III) and cephamycin C(IV), were separated on a column (20 cm x 4.6 mm) of Spherisorb C8 with acetonitrile - 0.01 M phosphate buffer of pH 5.5 containing 0.01 M butylammonium hydroxide and 0.2% of acetic acid (1:19) as mobile phase (1.5 mL min-1), post-column derivatization with phthalaldehyde and 2-mercaptoethanol and fluorimetric detection at 450 nm (excitation at 350 nm). Hydrolysis on a column of Amberlite IRA-120 before derivatization improved sensitivity for, e.g., III. Calibration graphs for (IV) and adicillin (V) were rectilinear in the range 0 to 100 µg mL-1. In analysis of a sample containing 100 µg mL-1 of (IV) the coefficient of variation was 2% (n = 20). The detection limits for (IV) and V were 0.5 to 1.0 µg mL-1 and for ampicillin, cephalexin and cephradine were 26, 14 and 8 µg mL-1, respectively.
HPLC Spectrophotometry Amberlite Post-column derivatization

"Determination Of Ampicillin In Biological Fluids By Coupled-column Liquid Chromatography And Post-column Derivatization"
J. Chromatogr. B 1991 Volume 567, Issue 1 Pages 121-128
K. Lanbeck-Vallén*, J. Carlqvist and T. Nordgren

Abstract: Plasma (0.5 ml) was mixed vigorously with 70% trichloracetic acid in Na2PO4 - citric acid buffer solution, pH 5.4 (200 µL) and centrifuged at 2400 g for 10 min. A portion (400 µL) of the supernatant liquid was mixed with 1 M NaOH (85 µL) to adjust the pH to ~5. Paediatric plasma (100 µL) was treated in a similar manner. Urine was diluted with 0.5 M Na2PO4 - citric acid buffer solution of pH 4.85. Portions (20 to 100 µL) of the solution were analyzed by HPLC on a column of Perkin Elmer 3 x 3 (3 µm) connected in series with a column (10 cm x 4.6 mm) of Microspher C18 (3 µm) with elution (1 mL min-1) with 17% methanol in phosphate buffer solution of pH 7.4 containing 1 mM Na hexylsulfate for the first column and 35% methanol (for plasma) or 30% methanol (for urine) in phosphate buffer solution of pH 7.4 for the second column. The eluate from the second column was reacted with fluorescamine (0.16 mg mL-1) in acetonitrile and the fluorescence was measured at 470 nm (excitation at 372 nm). Detection limits were 14 nM and 570 nM-of ampicillin in plasma and urine, respectively.
Blood Plasma Urine HPLC Fluorescence Buffer Column pH Post-column derivatization

"Determination Of Ampicillin Or Amoxycillin In Pharmaceutical Samples By Flow Injection Analysis"
J. Pharm. Biomed. Anal. 1994 Volume 12, Issue 12 Pages 1585-1589
M. S. García, C. Sánchez-Pedreño*, M. I. Albero and V. Ródenas

Abstract: Powdered capsule contents, suspensions or injection solutions equivalent to 37 mg of ampicillin (I) or 40 mg of amoxycillin (II) were dissolved in 1 mL of water (for I) or 1 mL of 1 M HCl (for II) and diluted to 100 mL with water. Portions (72 µL) were injected into a carrier stream (1.2 ml/min) of water which merged with a stream (1.2 ml/min) of 3 mM PdCl2 in 10 mM HCl before passing to a reactor (3 m x 0.5 mm i.d.) maintained at 40°C and on to a flow cell for detection at 400 nm. The calibration graphs for I and II were linear from 20 µM to 0.6 mM and the detection limits were 8 µM and 7.3 µM, respectively; the corresponding RSD were 0.16% and 0.22%. Recoveries were 99-102.2%. Sample throughput was 45/h. No interfering compounds were identified. The results agreed well those obtained by standard methods (European Pharmacopoeia Second Ed., Part II, volume 3, p. 260).
Pharmaceutical Spectrophotometry Interferences Standard method Method comparison

"Application Of Fuzzy-logic In Multicomponent Analysis By Optrodes"
Biosens. Bioelectron. 1997 Volume 12, Issue 9-10 Pages 917-923
Markus Wollenweber, Jürgen Polster*, Thomas Becker and Hanns-Ludwig Schmidt

Abstract: Fuzzy logic can be a useful tool for the determination of substrate concentrations applying optode arrays in combination with flow injection analysis, UV-VIS spectroscopy and kinetics. The transient diffuse reflectance spectra in the visible wavelength region from four optodes were evaluated to carry out the simultaneous determination of artificial mixtures of ampicillin and penicillin. The discrimination of the samples was achieved by changing the composition of the receptor gel and working pH. Different algorithms of pre-processing were applied on the data to reduce the spectral information to a few analytic-specific variables. These variables were used to develop the fuzzy model. After calibration the model was validated by an independent test data set. (C) 1997 Elsevier Science Limited. 21 References
Spectrophotometry Sensor Optosensing Multicomponent Chemometrics Fuzzy logic Kinetic

"Hydroxylaminolysis Of β-lactams And Its Use For The Determination Of Penicillins By Flow Injection Analysis"
Cesk. Farm. 1990 Volume 39, Issue 2 Pages 77-79
Karlicek, R.;Solich, P.

Abstract: A three-stream (0.6 mL min-1 each) system was used, containing three coils in series, of length 25, 50 and 100 cm (A, B and C, respectively). A sample (85 µL) was injected into a stream of reagent solution of pH 6.2 composed of 0.1 M hydroxylammonium chloride and 0.15% Brij-35 in aqueous 25% ethanol, the mixture was passed through reaction coil A (for hydrolysis of β-lactam rings), then acidified to pH ~1 by mixing with a stream of 0.5 M H2SO4 in coil B, merged with solution comprising 12.8 g of (NH4)2Fe(SO4)2 and 1 mL of 15% Brij-35 in 100 mL of 0.05 M H2SO4 - ethanol (3:1), and passed through coil C. The absorbance of the colored complex formed with Fe(III) was measured at 505 nm. Calibration graphs were rectilinear for 0.25 to 3 mg mL-1 of ampicillin, benzylpenicillin, procaine penicillin or phenoxymethylpenicillin, and the detection limits were ~0.1 mg mL-1. The coefficient of variation (n = 6 to 10) were 1.5% for ~1 mg mL-1 of individual penicillins. The method is suitable for analysis of pharmaceuticals; throughput is 50 h-1.
Pharmaceutical Spectrophotometry pH Calibration