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C1613

Carbenicillin

Name: Carbenicillin
Brand: SIGMA

Ready Made Solution, 100 mg/mL in ethanol/water

Synonym(s):

α-Carboxybenzylpenicillin solution

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₁₈N₂O₆S

Molecular Weight:

378.40

NACRES:

NA.85

PubChem Substance ID:

24892425

UNSPSC Code:

51282404

MDL number:

MFCD00242604

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Properties

Quality Segment

200

form

liquid, ready-to-use solution

concentration

100 mg/mL in ethanol/water

solubility

H₂O: 100 mg/mL, ethanol: 100 mg/mL

suitability

suitable for testing specifications (Bacteriostatic (cell type) E. Coli DH5a, result: pass)

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

cell wall synthesis | interferes

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1

InChI key

FPPNZSSZRUTDAP-UWFZAAFLSA-N

Description

General description

Chemical structure: β-lactam

Application

Carbenicillin is used for selection of Ampicillin-resistant transformed cells. It is used to study the role of penicillin-sensitive transpeptidases in the process cell wall biosynthesis.

Biochem/physiol Actions

Carbenicillin is an ampicillin analog with structure related to benzyl penicillin. It is effective against Gram-negative bacteria and exhibits limited activity against Gram-positive bacteria. Carbenicillin binds and inhibits the enzymes involved in the synthesis of bacterial cell wall. Since carbenicillin is less sensitive to β-lactamases than ampicillin, it is effective against ampicillin-resistant bacteria. It has superior stability at low pH and acts as a selection agent. Effective concentration of carbenicillin: 50 to 100 μg/ml.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.