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A6140

Sigma-Aldrich

Ampicillin trihydrate

900-1050 μg/mg anhydrous basis (HPLC)

Synonym(s):

α-Aminobenzylpenicillin trihydrate, Aminobenzyl Penicillin, Ampicillin, D-(−)-α-Aminobenzylpenicillin

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About This Item

Empirical Formula (Hill Notation):
C16H19N3O4S · 3H2O
CAS Number:
7177-48-2
Molecular Weight:
403.45
Beilstein:
5399534
EC Number:
200-709-7
MDL number:
MFCD00072036
UNSPSC Code:
51281703
PubChem Substance ID:
57653869
NACRES:
NA.85

form

powder or crystals

concentration

900-1050 μg/mg (anhydrous, HPLC)

mp

198-200 °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

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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General description

Chemical structure: ß-lactam

Application

Ampicillin Trihydrate is commonly 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.

Other Notes

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H317,H319,H334,H335

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

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H J Nelis et al.
Antimicrobial agents and chemotherapy, 36(8), 1606-1610 (1992-08-01)
The determination of ampicillin in plasma and serum by reversed-phase high-performance liquid chromatography with UV detection suffers from poor selectivity and sensitivity. Currently, the most common approach to overcoming these problems consists of improving the compound's detectability via pre- or
Ramendra K Singh et al.
European journal of medicinal chemistry, 45(3), 1078-1086 (2009-12-26)
Curcumin bioconjugates, viz. di-O-tryptophanylphenylalanine curcumin (2), di-O-decanoyl curcumin (3), di-O-pamitoyl curcumin (4), di-O-bis-(gamma,gamma)folyl curcumin (6), C(4)-ethyl-O-gamma-folyl curcumin (8) and 4-O-ethyl-O-gamma-folyl curcumin (10) have been synthesized and tested for their antibacterial and antiviral activities. The conjugates 2, 3, 4, 6 and
Sherif A F Rostom et al.
Bioorganic & medicinal chemistry, 17(2), 882-895 (2008-12-17)
The synthesis of two groups of structure hybrids comprising basically the antipyrine moiety attached to either polysubstituted thiazole or 2,5-disubstituted-1,3,4-thiadiazole counterparts through various linkages is described. Twelve out of the newly synthesized compounds were evaluated for their anti-inflammatory activity using
Ebtehal S Al-Abdullah et al.
European journal of medicinal chemistry, 46(9), 4642-4647 (2011-08-19)
New series of 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles namely, 2-substitued thio-6-phenyl-3,4-dihydro-4-oxopyrimidine-5-carbonitriles (5a-d, 6, 7a-d, 8), 2-(4-chlorobenzylthio)-4-chloro-6-phenylpyrimidine-5-carbonitrile (9), 2-(4-chlorobenzylthio)-4-arylthio-6-phenylpyrimidine-5-carbonitriles (10a-d) and 2-(4-chlorobenzylthio)-4-arylamino-6-phenylpyrimidine-5-carbonitriles (11a-d) was synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus
Sherif A F Rostom et al.
Bioorganic & medicinal chemistry, 17(6), 2410-2422 (2009-03-03)
The azole pharmacophore is still considered a viable lead structure for the synthesis of more efficacious and broad spectrum antimicrobial agents. Potential antibacterial and antifungal activities are encountered with some tetrazoles. Therefore, this study presents the synthesis and antimicrobial evaluation
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