Ampicillin
SIGMA/A9393 - anhydrous, 96.0-102.0% (anhydrous basis)
Synonym: (-
CAS Number: 69-53-4
Empirical Formula (Hill Notation): C16H19N3O4S
Molecular Weight: 349.40
EC Number: 200-709-7
MDL Number: MFCD00005175
Linear Formula: C16H19N3O4S
Product Type: Chemical
| antibiotic activity spectrum | Gram-negative bacteria |
| Gram-positive bacteria | |
| assay | 96.0-102.0% (anhydrous basis) |
| form | solid |
| InChI | 1S/C16H19N3O4S/c1-16(2)11 |
| InChI key | AVKUERGKIZMTKX-NJBDSQKTSA |
| mode of action | cell wall synthesis | interferes |
| mp | 208 °C (dec.) (lit.) |
| pKa (25 °C) | 2.5 (COOH) |
| 7.3 (NH2) | |
| Quality Level | 200  |
| SMILES string | [H][C@]12SC(C)(C)[C@@H](N |
| storage temp. | 2-8°C |
| Application: | Ampicillin 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. |
| Biochem/physiol Actions: | β-lactams are inactivated by β-lactamases and for this reason ampicillin is used with a β-lactamase inhibitor. |
| 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. |
| General description: | Chemical structure: ß-lactam |
| Other Notes: | Store under argon. Keep container tightly closed in a dry and well-ventilated place, hygroscopic. |
| 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 |
| Hazard Codes | Xn |
| Risk Statements | 36/37/38-42/43 |
| Safety Statements | 22-26-36/37 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 2 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | 96.0-102.0% (anhydrous basis) |
| mp | 208 °C (dec.) (lit.) |
| Storage Temp. | 2-8°C |
| UNSPSC | 51101500 |