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Merck

C1389

Sigma-Aldrich

Carbenicillin disodium salt

89.0-100.5% anhydrous basis

Sinónimos:

Carbenicillin, Disodium carbenicillin, α-Carboxybenzylpenicillin disodium salt

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About This Item

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

biological source

synthetic (chemical)

Quality Level

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

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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

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.
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

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

Storage and Stability

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.

Comparable product

Referencia del producto
Descripción
Precios

Pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

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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Boris Rodenko et al.
Nature protocols, 1(3), 1120-1132 (2007-04-05)
Major histocompatibility complex (MHC) class I molecules present peptide ligands on the cell surface for recognition by appropriate cytotoxic T cells. MHC-bound peptides are critical for the stability of the MHC complex, and standard strategies for the production of recombinant
Edward Avilés et al.
Organic letters, 12(22), 5290-5293 (2010-10-23)
Monamphilectine A (1), a new diterpenoid β-lactam alkaloid showing potent antimalarial activity, was isolated in milligram quantities following bioassay-directed extraction of a Puerto Rican marine sponge Hymeniacidon sp. Its structure, established by interpretation of spectral data, was confirmed unequivocally by
Sua Lee et al.
Frontiers in immunology, 12, 778829-778829 (2021-12-07)
Since the coronavirus disease outbreak in 2019, several antibody therapeutics have been developed to treat severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) infections. Antibody therapeutics are effective in neutralizing the virus and reducing hospitalization in patients with mild and moderate
Gina M Geiselman et al.
Microbial cell factories, 19(1), 24-24 (2020-02-07)
Rhodosporidium toruloides has emerged as a promising host for the production of bioproducts from lignocellulose, in part due to its ability to grow on lignocellulosic feedstocks, tolerate growth inhibitors, and co-utilize sugars and lignin-derived monomers. Ent-kaurene derivatives have a diverse
Brigitte K Ziervogel et al.
Structure (London, England : 1993), 21(1), 76-87 (2012-12-04)
The structure of OmpF porin in complex with three common antibiotics (zwitterionic ampicillin, anionic ertapenem, and di-anionic carbenicillin) was determined using X-ray crystallography. The three antibiotics are found to bind within the extracellular and periplasmic pore vestibules, away from the

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