C1389

Carbenicillin disodium salt

89.0-100.5% anhydrous basis

• Synonym(s): Carbenicillin, Disodium carbenicillin, α-Carboxybenzylpenicillin disodium salt
• Empirical Formula (Hill Notation): C₁₇H₁₆N₂Na₂O₆S
• CAS Number: 4800-94-6
• Molecular Weight: 422.36
• Beilstein: 5722128
• EC Number: 225-360-8
• MDL number: MFCD00077683
• UNSPSC Code: 51282413
• PubChem Substance ID: 24892409
• NACRES: NA.76

Properties

• biological source: synthetic (chemical)
• Quality Level: 200
• 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

Description

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[1]
• as a selective agent in the culture media to prevent the growth of bacterial contaminants[2]
• in a study focused on the development of monoclonal antibodies[3]

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

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.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H317,H334
• Precautionary Statements: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• 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