Ampicillin
USP/1033000 - United States Pharmacopeia (USP) Reference Standard
Synonym: D-(−)-α-Aminobenzylpenicillin
CAS Number: 69-53-4
Empirical Formula (Hill Notation): C16H19N3O4S
Molecular Weight: 349.40
MDL Number: MFCD00005175
Linear Formula: C16H19N3O4S
Product Type: Chemical
| application(s) | pharmaceutical (small molecule) |
| description | API family: ampicillin |
| format | neat |
| grade | pharmaceutical primary standard |
| InChI | 1S/C16H19N3O4S/c1-16(2)11 |
| InChI key | AVKUERGKIZMTKX-NJBDSQKTSA |
| manufacturer/tradename | USP |
| mp | 208 °C (dec.) (lit.) |
| SMILES string | [H][C@]12SC(C)(C)[C@@H](N |
| storage temp. | 2-8°C |
| 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. |
| 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. |
| 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   . |
| Other Notes: | USP issued SDS can be found here . |
| 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. |
| Symbol |   GHS07,GHS08 |
| Signal word | Danger |
| Hazard statements | H315 - H317 - H319 - H334 - H335 |
| Precautionary statements | P280 - P302 + P352 - P305 + P351 + P338 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 2 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| mp | 208 °C (dec.) (lit.) |
| Storage Temp. | 2-8°C |
| UNSPSC | 41116107 |