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C9231

Sigma-Aldrich

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
Beilstein:
5722128
EC Number:
225-360-8
MDL number:
MFCD00077683
UNSPSC Code:
51101500
PubChem Substance ID:
24893142
NACRES:
NA.76

Agency

USP/NF
meets USP testing specifications

Quality Level

200

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

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

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

Analysis Note

Stable at 37 °C for 3 days

Other Notes

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

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Precautionary Statements

P261 - P280 - P342 + P311

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Yasser M Abdelrahman et al.
Nucleic acids research, 39(5), 1843-1854 (2010-11-06)
Chlamydia trachomatis is an obligate intracellular bacterium that exhibits a unique biphasic developmental cycle that can be disrupted by growth in the presence of IFN-γ and β-lactams, giving rise to an abnormal growth state termed persistence. Here we have examined
Steven D Brown et al.
Biochemistry, 48(47), 11155-11157 (2009-10-24)
Bacteriophage Qbeta coat protein forms uniform virus-like particles when expressed recombinantly in a variety of organisms. We have inserted the IgG-binding Z domain at the carboxy terminus of the coat protein and coexpressed this chimeric subunit with native coat protein
J Steinmann et al.
Euro surveillance : bulletin Europeen sur les maladies transmissibles = European communicable disease bulletin, 16(33) (2011-08-30)
We describe the epidemiology and characteristics of the pathogen and patients (n=7) associated with an outbreak of a carbapenem-resistant Klebsiella pneumoniae (CRKP) strain in a German university hospital from July 2010 to January 2011. Species identification and detection of carbapenem
Lintao Zeng et al.
Chemical communications (Cambridge, England), 46(14), 2435-2437 (2010-04-10)
A fluorescent probe (QA) based on quinine bearing two quaternary ammonium groups and a long hydrophobic chain was synthesized, and it showed highly selective recognition of carbenicillin (a typical beta-lactam antibiotic) in 100% aqueous solution via concerted interactions.
Jiachuan Pan et al.
PloS one, 7(9), e45778-e45778 (2012-10-03)
Bacteria are well known to form dormant persister cells that are tolerant to most antibiotics. Such intrinsic tolerance also facilitates the development of multidrug resistance through acquired mechanisms. Thus persister cells are a promising target for developing more effective methods
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