A9393

Ampicillin

anhydrous, 96.0-102.0% (anhydrous basis)

• Synonyme(s) : (-)-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
• Formule empirique (notation de Hill): C₁₆H₁₉N₃O₄S
• Numéro CAS: 69-53-4
• Poids moléculaire : 349.40
• Numéro Beilstein : 1090925
• Numéro CE : 200-709-7
• Numéro MDL: MFCD00005175
• Code UNSPSC : 51281703
• ID de substance PubChem : 24891442
• Nomenclature NACRES : NA.85

Propriétés

• Niveau de qualité: 200
• Pureté: 96.0-102.0% (anhydrous basis)
• Forme: solid
• pKa (25 °C): 2.5 (COOH); 7.3 (NH2)
• Pf: 208 °C (dec.) (lit.)
• Spectre d'activité de l'antibiotique: Gram-negative bacteria; Gram-positive bacteria
• Mode d’action: cell wall synthesis | interferes
• Température de stockage: 2-8°C
• Chaîne SMILES: [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
• Clé InChI: AVKUERGKIZMTKX-NJBDSQKTSA-N

Description

Description générale

Chemical structure: ß-lactam

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.

Actions biochimiques/physiologiques

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.

Attention

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.

Notes préparatoires

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.

Autres remarques

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

Informations sur la sécurité

• Pictogrammes: GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H317,H334
• Conseils de prudence: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Classification des risques: Resp. Sens. 1 - Skin Sens. 1
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 2
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Faceshields, Gloves