Merck
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A9393

Sigma-Aldrich

Ampicillin

anhydrous, 96.0-102.0% (anhydrous basis)

Synonym(s):
D-(−)-α-Aminobenzylpenicillin
Empirical Formula (Hill Notation):
C16H19N3O4S
CAS Number:
Molecular Weight:
349.40
Beilstein:
1090925
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.85

Nível de qualidade

200

teor

96.0-102.0% (anhydrous basis)

forma

solid

pKa (25 °C)

2.5 (COOH)
7.3 (NH2)

pf

208 °C (dec.) (lit.)

espectro de atividade do antibiótico

Gram-negative bacteria
Gram-positive bacteria

Modo de ação

cell wall synthesis | interferes

temperatura de armazenamento

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

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Descrição geral

Chemical structure: ß-lactam

Aplicação

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.

Ações bioquímicas/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.

Atenção

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 preparo

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.

Outras notas

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

Pictogramas

Health hazard

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

Resp. Sens. 1 - Skin Sens. 1

Código de classe de armazenamento

11 - Combustible Solids

WGK

WGK 2

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificate of Analysis

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Certificate of Origin

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