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Merck

C1389

Carbenicillin disodium salt

89.0-100.5% anhydrous basis

Sinónimos:

Carbenicillin, Disodium carbenicillin, α-Carboxybenzylpenicillin disodium salt

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Fórmula empírica (notación de Hill):
C17H16N2Na2O6S
Número CAS:
Peso molecular:
422.36
UNSPSC Code:
51282413
NACRES:
NA.76
PubChem Substance ID:
EC Number:
225-360-8
Beilstein/REAXYS Number:
5722128
MDL number:
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biological source

synthetic (chemical)

Quality Segment

assay

89.0-100.5% anhydrous basis

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

[Na+].[Na+].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.2Na/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);;/q;2*+1/p-2/t9?,10-,11+,14-;;/m1../s1

InChI key

RTYJTGSCYUUYAL-YCAHSCEMSA-L

General description

Carbenicillin is a semi-synthetic, broad-spectrum carboxypenicillin antibiotic with bactericidal and beta-lactamase resistant activity. It is a broad-spectrum antibiotic, meaning that it is effective against a wide range of bacteria, including both Gram-positive and Gram-negative bacteria. Carbenicillin is particularly useful against Pseudomonas aeruginosa, a Gram-negative bacterium that is often resistant to other antibiotics.

Carbenicillin is commonly used in cell biology applications to prevent the growth of bacterial contaminants. It is also used in microbiology to select for bacteria that have been transformed with a vector harboring the gene encoding beta-lactamase, which makes them resistant to carbenicillin.

Application

Carbenicillin disodium salt has been used:

  • in the preparation of Luria-Bertani (LB) agar plates and media
  • as a selective agent in the culture media to prevent the growth of bacterial contaminants
  • in a study focused on the development of monoclonal antibodies

Biochem/physiol Actions

Mode of Action: Carboxypenicillin antibiotic that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane.


Antimicrobial spectrum: Active against Gram-positive and Gram-negative bacteria
Carbenicillin acylates the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation prevents the cross-linkage of peptidoglycan strands, thereby inhibiting the third and last stage of bacterial cell wall synthesis. This leads to incomplete bacterial cell wall synthesis and eventually causes cell lysis.

Features and Benefits

  • Broad-spectrum antibiotic with bactericidal and beta-lactamase resistant activity
  • Effective against a wide range of bacteria, including Pseudomonas aeruginosa
  • Commonly used in Cell Biology and Biochemical applications
  • Offers greater stablility than ampicillin

Preparation Note

Tightly closed. Dry. Keep locked up or in an area accessible only to qualified or authorized

Analysis Note

Stable at 37 °C for 3 days

Other Notes

For additional information on our range of Biochemicals, please complete this form.
Keep container tightly closed in a dry and well-ventilated place.


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pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves



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