A9393

Ampicillin

anhydrous, 96.0-102.0% (anhydrous basis)

• Sinónimos: (-)-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
• Fórmula empírica (notación de Hill): C₁₆H₁₉N₃O₄S
• Número de CAS: 69-53-4
• Peso molecular: 349.40
• Beilstein: 1090925
• Número CE: 200-709-7
• Número MDL: MFCD00005175
• Código UNSPSC: 51281703
• ID de la sustancia en PubChem: 24891442
• NACRES: NA.85

Propiedades

• Nivel de calidad: 200
• Ensayo: 96.0-102.0% (anhydrous basis)
• Formulario: solid
• pKa (25 °C): 2.5 (COOH); 7.3 (NH2)
• mp: 208 °C (dec.) (lit.)
• espectro de actividad antibiótica: Gram-negative bacteria; Gram-positive bacteria
• Modo de acción: cell wall synthesis | interferes
• temp. de almacenamiento: 2-8°C
• cadena 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
• Clave InChI: AVKUERGKIZMTKX-NJBDSQKTSA-N

Descripción

Descripción general

Chemical structure: ß-lactam

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Precaución

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 de preparación

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.

Otras notas

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

Información de seguridad

• Pictogramas: GHS08
• Palabra de señalización: Danger
• Frases de peligro: H317,H334
• Consejos de prudencia: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Clasificaciones de peligro: Resp. Sens. 1 - Skin Sens. 1
• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 2
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: dust mask type N95 (US), Eyeshields, Faceshields, Gloves