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Merck
CN

C9231

Carbenicillin disodium

meets USP testing specifications

Synonym(s):

Carbenicillin disodium salt, α-Carboxybenzylpenicillin disodium salt

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About This Item

Empirical Formula (Hill Notation):
C17H16N2Na2O6S
CAS Number:
4800-94-6
Molecular Weight:
422.36
UNSPSC Code:
51102829
NACRES:
NA.76
PubChem Substance ID:
24893142
EC Number:
225-360-8
Beilstein/REAXYS Number:
5722128
MDL number:
MFCD00077683

Key Documents

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Product Name

Carbenicillin disodium, meets USP testing specifications

InChI key

RTYJTGSCYUUYAL-YCAHSCEMSA-L

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

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

agency

USP/NF
meets USP testing specifications

form

solid

solubility

H2O: 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

application(s)

pharmaceutical (small molecule)

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

Quality Level

200

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Analysis Note

Stable at 37 °C for 3 days

Application

Used for selection of ampr transformed cells. Used to study the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.

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

General description

Chemical structure: ß-lactam

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000511778
0000511778
0000504450
0000504449
0000504449

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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
Sarah Sainsbury et al.
Journal of molecular biology, 405(1), 173-184 (2010-10-27)
We report the first crystal structures of a penicillin-binding protein (PBP), PBP3, from Pseudomonas aeruginosa in native form and covalently linked to two important β-lactam antibiotics, carbenicillin and ceftazidime. Overall, the structures of apo and acyl complexes are very similar;
Nina Möker et al.
Journal of bacteriology, 192(7), 1946-1955 (2010-01-26)
Bacterial persister cells constitute a small portion of a culture which is tolerant to killing by lethal doses of bactericidal antibiotics. These phenotypic variants are formed in numerous bacterial species, including those with clinical relevance like the opportunistic pathogen Pseudomonas
John R Zupan et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(22), 9060-9065 (2013-05-16)
Growth and cell division in rod-shaped bacteria have been primarily studied in species that grow predominantly by peptidoglycan (PG) synthesis along the length of the cell. Rhizobiales species, however, predominantly grow by PG synthesis at a single pole. Here we
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
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