Skip to Content
Merck
All Photos(1)

Documents

C1389

Sigma-Aldrich

Carbenicillin disodium salt

89.0-100.5% anhydrous basis

Synonym(s):

Carbenicillin, Disodium carbenicillin, α-Carboxybenzylpenicillin disodium salt

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C17H16N2Na2O6S
CAS Number:
Molecular Weight:
422.36
Beilstein:
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

Looking for similar products? Visit Product Comparison Guide

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.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
J Steinmann et al.
Euro surveillance : bulletin Europeen sur les maladies transmissibles = European communicable disease bulletin, 16(33) (2011-08-30)
We describe the epidemiology and characteristics of the pathogen and patients (n=7) associated with an outbreak of a carbapenem-resistant Klebsiella pneumoniae (CRKP) strain in a German university hospital from July 2010 to January 2011. Species identification and detection of carbapenem
Catherine Kaminski et al.
Critical care (London, England), 15(2), R112-R112 (2011-04-13)
Although Pseudomonas aeruginosa is a leading pathogen responsible for ventilator-associated pneumonia (VAP), the excess in mortality associated with multi-resistance in patients with P. aeruginosa VAP (PA-VAP), taking into account confounders such as treatment adequacy and prior length of stay in

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service