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Key Documents

21800

Sigma-Aldrich

Carbenicillin disodium salt

≥90% (anhydrous basis)

Synonym(s):

α-Carboxybenzylpenicillin disodium salt

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About This Item

Empirical Formula (Hill Notation):
C17H16N2Na2O6S
CAS Number:
Molecular Weight:
422.36
Beilstein/REAXYS Number:
5722128
EC Number:
MDL number:
UNSPSC Code:
51101500

assay

≥90% (anhydrous basis)

solubility

H2O: 50 mg/mL

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

Chemical structure: ß-lactam

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

Analysis Note

Stable at 37 °C for 3 days

Other Notes

Parenteral antibiotic active against Pseudomonas aeruginosa.; Characterization of two chromosome-encoded β-lactamases from Citrobacter diversus ULA-27

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pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

13 - Non 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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G Amicosante et al.
The Biochemical journal, 254(3), 885-890 (1988-09-15)
Two chromosome-encoded beta-lactamases have been purified from Citrobacter diversus ULA-27. They exhibited slightly different isoelectric points (6.8 and 6.2) and very similar Mr values (congruent to 29,000). Their specificity spectrum was rather wide, since they hydrolysed some cephalosporins with kcat:
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
Liang Yang et al.
Journal of microbiology (Seoul, Korea), 49(1), 107-114 (2011-03-04)
Resistance-Nodulation-Cell Division (RND) pumps play important roles in bacterial resistance to antibiotics. Pseudomonas aeruginosa is an important human pathogen which exhibits high level resistance to antibiotics. There are total of 12 RND pumps present in the P. aeruginosa PAOl genome.
Olivier Fisette et al.
Biophysical journal, 103(8), 1790-1801 (2012-10-23)
The effects of substrate binding on class A β-lactamase dynamics were studied using molecular dynamics simulations of two model enzymes; 40 100-ns trajectories of the free and substrate-bound forms of TEM-1 (with benzylpenicillin) and PSE-4 (with carbenicillin) were recorded (totaling
Paromita Raha et al.
Biochemistry, 49(45), 9809-9819 (2010-10-07)
Conformational switching upon core RNA polymerase binding is an integral part of functioning of bacterial sigma factors. Here, we have studied dynamical features of two alternative sigma factors. A study of fluorescence resonance energy transfer and hydrodynamic measurements in Escherichia

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