EMAIL THIS PAGE TO A FRIEND
1033000 USP

Ampicillin

United States Pharmacopeia (USP) Reference Standard

Synonym: D-(−)-α-Aminobenzylpenicillin

  • CAS Number 69-53-4

  • Empirical Formula (Hill Notation) C16H19N3O4S

  • Molecular Weight 349.40

  •  Beilstein/REAXYS Number 1090925

  •  MDL number MFCD00005175

  •  PubChem Substance ID 329749022

  •  NACRES NA.24

Purchase

Properties

Related Categories Analytical Standards, Analytical/Chromatography, Pharmacopeia & Metrological Institutes Standards, USP Standards, USP Standards A - B More...
grade   pharmaceutical primary standard
form   neat
mfr. no.   USP
mp   208 °C (dec.) (lit.)
Featured Industry   Pharmaceutical (small molecule)
format   neat
SMILES string   [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c3ccccc3)C(O)=O
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

Description

Application

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.

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.

Caution

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.

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.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

USP issued SDS can be found here.

Legal Information

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number
Protocols & Articles

Articles

HPLC Analysis of β-Lactam Antibiotics on Discovery® RP-Amide C16

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of β-Lactam Antibiotics on Discovery® RP-Amide C16
Keywords: Antibiotics, Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

Related Products

related product

Product #

Description

Add to Cart

08168 Timestrip Plus 8 °C

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?