31591

Supelco

Ampicillin trihydrate

VETRANAL®, analytical standard

Synonym(s):
D-(−)-α-Aminobenzylpenicillin
Empirical Formula (Hill Notation):
C16H19N3O4S · 3H2O
CAS Number:
Molecular Weight:
403.45
Beilstein/REAXYS Number:
5399534
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.24
Pricing and availability is not currently available.

Quality Level

grade

analytical standard

product line

VETRANAL®

form

neat

shelf life

limited shelf life, expiry date on the label

application(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white to off-white

mp

198-200 °C (dec.) (lit.)

Featured Industry

Clinical
Forensics and Toxicology
Pharmaceutical (small molecule)

Mode of action

cell wall synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

format

neat

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

Ampicillin trihydrate is a stable hydrated form of ampicillin.
Chemical structure: ß-lactam

Application

Ampicillin trihydrate has been used as reference standard for determining the residual solvents and its effect on ampicillin trihydrate crystal structure using GC, X-ray powder diffraction (XRPD) and Fourier transform infrared spectroscopy (FT-IR).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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

250 mg

Other Notes

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

Legal Information

VETRANAL is a registered trademark of Sigma-Aldrich Chemie GmbH

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Determination of residual solvents and investigation of their effect on ampicillin trihydrate crystal structure.
Nojavan S
Journal of Pharmaceutical and Biomedical Analysis, 4;36(5), 983-988 (2005)
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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