Ampicillin, 5G

SKU:
A9393-5G
  • $79.20

    • Description

    Ampicillin, 5G

    anhydrous, 96.0-102.0% (anhydrous basis)

    Synonym(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
    Empirical Formula (Hill Notation):
    C16H19N3O4S
    CAS Number:
    69-53-4
    Molecular Weight:
    349.40
    Beilstein:
    1090925
    EC Number:
    200-709-7
    MDL number:
    MFCD00005175
    PubChem Substance ID:
    24891442
    NACRES:
    NA.85

    PROPERTIES

    Quality Level

    200

    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

    DESCRIPTION

    General description

    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.[1][2][3][4]

    Biochem/physiol Actions

    β-lactams are inactivated by β-lactamases and for this reason ampicillin is used with a β-lactamase inhibitor.[5][6][7]
    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.

    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.

    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.

    SAFETY INFORMATION

    Signal Word

    Danger

    Hazard Statements

    H317 - H334

    Precautionary Statements

    P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313

    Hazard Classifications

    Resp. Sens. 1 - Skin Sens. 1

    Storage Class Code

    11 - Combustible Solids

    WGK

    WGK 2

    Flash Point(F)

    Not applicable

    Flash Point(C)

    Not applicable

    Personal Protective Equipment

    dust mask type N95 (US), Eyeshields, Gloves