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Merck
CN

271861

Sigma-Aldrich

Ampicillin

99%

Synonym(s):

D-(−)-α-Aminobenzylpenicillin

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About This Item

Empirical Formula (Hill Notation):
C16H19N3O4S
CAS Number:
Molecular Weight:
349.40
Beilstein:
1090925
EC Number:
MDL number:
UNSPSC Code:
12352103
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Assay

99%

optical activity

[α]20/D +297°, c = 0.25 in H2O

mp

208 °C (dec.) (lit.)

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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Biochem/physiol Actions

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.

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