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Merck
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Key Documents

C1613

Sigma-Aldrich

Carbenicillin

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

Synonyme(s) :

α-Carboxybenzylpenicillin solution

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About This Item

Formule empirique (notation de Hill):
C17H18N2O6S
Poids moléculaire :
378.40
Numéro MDL:
MFCD00242604
Code UNSPSC :
51282404
ID de substance PubChem :
24892425
Nomenclature NACRES :
NA.85

Stérilité

0.2 μm filtered

Forme

liquid

Concentration

100 mg/mL in ethanol/water

Solubilité

H2O: 100 mg/mL
ethanol: 100 mg/mL

Adéquation

suitable for testing specifications (Bacteriostatic (cell type) E. Coli DH5a, result: pass)

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

cell wall synthesis | interferes

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

FPPNZSSZRUTDAP-UWFZAAFLSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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.

Pictogrammes

FlameHealth hazard
GHS02,GHS08

Mention d'avertissement

Danger

Mentions de danger

H226,H317,H334

Classification des risques

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

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

104.0 °F - closed cup

Point d'éclair (°C)

40 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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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.
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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