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C1613

Sigma-Aldrich

Carbenicillin

Ready Made Solution, 100 mg/mL in ethanol/water, 0.2 μm filtered

Synonym(s):

α-Carboxybenzylpenicillin solution

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About This Item

Empirical Formula (Hill Notation):
C17H18N2O6S
Molecular Weight:
378.40
MDL number:
MFCD00242604
UNSPSC Code:
51101500
PubChem Substance ID:
24892425
NACRES:
NA.85

Quality Level

200

sterility

0.2 μm filtered

form

liquid

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

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General description

Chemical structure: ß-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.

Pictograms

FlameHealth hazard
GHS02,GHS08

Signal Word

Danger

Hazard Statements

H226,H317,H334

Hazard Classifications

Flam. Liq. 3 - Resp. Sens. 1 - Skin Sens. 1

WGK

WGK 2

Flash Point(F)

104.0 °F

Flash Point(C)

40 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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G N Rolinson
The Journal of antimicrobial chemotherapy, 41(6), 589-603 (1998-08-01)
For more than 40 years the author has been involved in research in the field of beta-lactam antibiotics. Much of this work was concerned with the development of the semisynthetic penicillins, following the isolation of the penicillin nucleus, 6-aminopenicillanic acid.
Andrea Brenna et al.
AMB Express, 4, 43-43 (2014-06-21)
Agrobacterium tumefaciens-mediated transformation is a powerful tool for reverse genetics and functional genomic analysis in a wide variety of plants and fungi. Tuber spp. are ecologically important and gastronomically prized fungi ("truffles") with a cryptic life cycle, a subterranean habitat
A J Wright
Mayo Clinic proceedings, 74(3), 290-307 (1999-03-25)
The penicillin family of antibiotics remains an important part of our antimicrobial armamentarium. In general, these agents have bactericidal activity, excellent distribution throughout the body, low toxicity, and efficacy against infections caused by susceptible bacteria. The initial introduction of aqueous
Kunihiko Nishino et al.
Antimicrobial agents and chemotherapy, 54(5), 2239-2243 (2010-03-10)
NlpE, an outer membrane lipoprotein, functions during envelope stress responses in Gram-negative bacteria. In this study, we report that overproduction of NlpE increases multidrug and copper resistance through activation of the genes encoding the AcrD and MdtABC multidrug efflux pumps
Maria Tomás et al.
Antimicrobial agents and chemotherapy, 54(5), 2219-2224 (2010-03-03)
Expression of ampC, oprD, mexA, mexC, mexE, and mexX was studied in 25 Pseudomonas aeruginosa isolates from cystic fibrosis patients, including 14 isolates of the Liverpool epidemic strain. Overexpressed mexA or ampC and reduced oprD were associated with beta-lactam resistance.
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