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Fórmula empírica (notación de Hill):
C16H19N3O4S
Número CAS:
Peso molecular:
349.40
UNSPSC Code:
51281703
NACRES:
NA.85
PubChem Substance ID:
EC Number:
200-709-7
Beilstein/REAXYS Number:
1090925
MDL number:
Servicio técnico
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Permítanos ayudarleQuality Level
assay
96.0-102.0% (anhydrous basis)
form
solid
pKa (25 °C)
2.5 (COOH), 7.3 (NH2)
mp
208 °C (dec.) (lit.)
antibiotic activity spectrum
Gram-negative bacteria, Gram-positive bacteria
mode of action
cell wall synthesis | interferes
storage temp.
2-8°C
SMILES string
[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
InChI key
AVKUERGKIZMTKX-NJBDSQKTSA-N
General description
Chemical structure: β-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.
Biochem/physiol Actions
Mode of Action: Ampicillin is a semisynthetic penicillin and a β-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 β-lactamase cleaves the β-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.
Mode of Resistance: Administration with β-lactamase cleaves the β-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.
β-lactams are inactivated by β-lactamases and for this reason ampicillin is used with a β-lactamase inhibitor.
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.
Other Notes
Store under argon. Keep container tightly closed in a dry and well-ventilated place, hygroscopic.
Disclaimer
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.
signalword
Danger
hcodes
Hazard Classifications
Resp. Sens. 1 - Skin Sens. 1
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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