A9393

Ampicillin

anhydrous, 96.0-102.0% (anhydrous basis)

• Sinonimo/i: (-)-6-(2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, Ampicillin acid, Ampicillin anhydrous, D-(−)-α-Aminobenzylpenicillin
• Formula empirica (notazione di Hill): C₁₆H₁₉N₃O₄S
• Numero CAS: 69-53-4
• Peso molecolare: 349.40
• Beilstein: 1090925
• Numero CE: 200-709-7
• Numero MDL: MFCD00005175
• Codice UNSPSC: 51281703
• ID PubChem: 24891442
• NACRES: NA.85

Proprietà

• Livello qualitativo: 200
• Saggio: 96.0-102.0% (anhydrous basis)
• Forma fisica: solid
• pKa (25 °C): 2.5 (COOH); 7.3 (NH2)
• Punto di fusione: 208 °C (dec.) (lit.)
• Spettro attività antibiotica: Gram-negative bacteria; Gram-positive bacteria
• Modalità d’azione: cell wall synthesis | interferes
• Temperatura di conservazione: 2-8°C
• Stringa SMILE: [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; AVKUERGKIZMTKX-NJBDSQKTSA-N

Descrizione

Descrizione generale

Chemical structure: ß-lactam

Applicazioni

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.

Azioni biochim/fisiol

β-lactams are inactivated by β-lactamases and for this reason ampicillin is used with a β-lactamase inhibitor.

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.

Avvertenza

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.

Nota sulla preparazione

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.

Altre note

Store under argon. Keep container tightly closed in a dry and well-ventilated place, hygroscopic.

Informazioni sulla sicurezza

• Pittogrammi: GHS08
• Avvertenze: Danger
• Indicazioni di pericolo: H317,H334
• Consigli di prudenza: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Classi di pericolo: Resp. Sens. 1 - Skin Sens. 1
• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 2
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable
• Dispositivi di protezione individuale: dust mask type N95 (US), Eyeshields, Faceshields, Gloves