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A1593

Sigma-Aldrich

Ampicillin

meets USP testing specifications

Synonym(s):
D-(−)-α-Aminobenzylpenicillin, Ampicillin trihydrate
Empirical Formula (Hill Notation):
C16H19N3O4S · 3H2O
CAS Number:
Molecular Weight:
403.45
Beilstein:
5399534
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.76

Quality Level

Agency/Method

USP/NF
meets USP testing specifications

form

solid

color

white

mp

198-200 °C (dec.) (lit.)

solubility

H2O: soluble 10 g/L

Featured Industry

Pharmaceutical (small molecule)

Mode of action

cell wall synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

storage temp.

2-8°C

SMILES string

O.O.O.CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(O)=O

InChI

1S/C16H19N3O4S.3H2O/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);3*1H2/t9-,10-,11+,14-;;;/m1.../s1

InChI key

RXDALBZNGVATNY-CWLIKTDRSA-N

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Related Categories

General description

Chemical structure: ß-lactam

Application

Used to select for ampicillin resistance in mutated and transformed cells.

Biochem/physiol Actions

A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.

Packaging

25g

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 2

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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Ramendra K Singh et al.
European journal of medicinal chemistry, 45(3), 1078-1086 (2009-12-26)
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Alexander V Semenov et al.
Applied and environmental microbiology, 75(10), 3206-3215 (2009-03-10)
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