59349
Ampicillin
analytical standard
Synonym(s):
D-(−)-α-Aminobenzylpenicillin
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About This Item
Empirical Formula (Hill Notation):
C16H19N3O4S
CAS Number:
Molecular Weight:
349.40
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
EC Number:
200-709-7
Beilstein/REAXYS Number:
1090925
MDL number:
Product Name
Ampicillin, analytical standard
InChI key
AVKUERGKIZMTKX-NJBDSQKTSA-N
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
SMILES string
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c3ccccc3)C(O)=O
grade
analytical standard
assay
≥95.0% anhydrous basis (NT)
shelf life
limited shelf life, expiry date on the label
technique(s)
HPLC: suitable
gas chromatography (GC): suitable
impurities
≤20% water
mp
208 °C (dec.) (lit.)
application(s)
clinical testing
format
neat
storage temp.
2-8°C
Quality Level
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Application
Ampicillin has been used as a reference compound in the determination of ampicillin free drug concentration in standard solution of human serum albumin by micellar liquid chromatography method.
Ampicillin is a semi-synthetic derivative of penicillin that functions as a broad-spectrum antibiotic. It has been used to study antibiotic resistance and penetration limitations, the synergy between multiple antibiotics, certain bloodstream infections, and has been used to develop PCR assays to detect resistance genes in cerebrospinal fluid.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Biochem/physiol Actions
Mode of Action: Ampicillin is a semisynthetic penicillin and a ß-lactam antibiotic that inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane.
Mode of Resistance: Administration with ß-lactamase cleaves the ß-lactam ring of Ampicillin and inactivates it.
Antimicrobial Spectrum: Effective against both Gram-positive (similar to benzylpenicillin) and Gram-negative bacteria (similar to tetracyclines and chloramphenicol.
Mode of Resistance: Administration with ß-lactamase cleaves the ß-lactam ring of Ampicillin and inactivates it.
Antimicrobial Spectrum: Effective against both Gram-positive (similar to benzylpenicillin) and Gram-negative bacteria (similar to tetracyclines and chloramphenicol.
Disclaimer
This product has been reported stable as supplied at 25°C at 43% and 81% relative humidity for six weeks. Additional studies have shown that the stability of Ampicillin in solution is a function of pH, temperature and the identity of the buffer. It′s activity is quickly lost when stored above pH 7. Optimal storage conditions are suggested as 2-8°C, and pH 3.8-5 where its activity was retained at 90%+ for a week.
General description
Chemical structure: β-lactam
Ampicillin belongs to the β-lactum group of antibiotics. It is used to treat bacterial infections via penetrating gram positive and gram negative bacteria. Its mode of action basically involves the inhibition of bacterial cell wall synthesis, thus leading to cell lysis.
Ampicillin belongs to the β-lactum group of antibiotics. It is used to treat bacterial infections via penetrating gram positive and gram negative bacteria. Its mode of action basically involves the inhibition of bacterial cell wall synthesis, thus leading to cell lysis.
Packaging
This product is packaged in a bottomless glass bottle with the contents inside an inserted fused cone.
Preparation Note
Ampicillin is reported as slightly soluble in water, practically insoluble in alcohol, chloroform, ether and fixed oils but soluble in dilute acids or bases. The solution should not be autoclaved; a stock solution should be sterilized through filtration and stored frozen, where it will be stable for months.
signalword
Danger
hcodes
Hazard Classifications
Resp. Sens. 1 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
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Analysis of three penicillin antibiotics (ampicillin, amoxicillin and cloxacillin) of several Iranian pharmaceutical companies by HPLC.
Ashnagar A and Naseri GN
Journal of Chemistry, 4(4), 536-545 (2007)
Rapid method for the determination of ampicillin residues in animal muscle tissues by high-performance liquid chromatography with fluorescence detection.
Luo W, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 694(2), 401-407 (1997)
A new application of micellar liquid chromatography in the determination of free ampicillin concentration in the drug?human serum albumin standard solution in comparison with the adsorption
Stepnik KE, et al.
Talanta, 153, 1-7 (2016)
Jens T Van Praet et al.
The EMBO journal, 34(4), 466-474 (2015-01-21)
Antinuclear antibodies are a hallmark feature of generalized autoimmune diseases, including systemic lupus erythematosus and systemic sclerosis. However, the processes underlying the loss of tolerance against nuclear self-constituents remain largely unresolved. Using mice deficient in lymphotoxin and Hox11, we report
Nuria Fernández-Hidalgo et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 56(9), 1261-1268 (2013-02-09)
The aim of this study was to compare the effectiveness of the ampicillin plus ceftriaxone (AC) and ampicillin plus gentamicin (AG) combinations for treating Enterococcus faecalis infective endocarditis (EFIE). An observational, nonrandomized, comparative multicenter cohort study was conducted at 17
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