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Safety Information

S9701

Sigma-Aldrich

Sulbactam

Synonym(s):

(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide, Betamaze, CP 45899, CP-45,899, Penicillanic acid 1,1-dioxide, Penicillanic acid S,S-dioxide, Penicillanic acid dioxide, Penicillanic acid sulfone

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About This Item

Empirical Formula (Hill Notation):
C8H11NO5S
CAS Number:
68373-14-8
Molecular Weight:
233.24
EC Number:
269-878-2
MDL number:
MFCD00867005
UNSPSC Code:
12352200
PubChem Substance ID:
329824632
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

100

form

powder

optical activity

[α]/D ≥+225°, c = 1 in H2O

color

white to tan

solubility

H2O: ≥18 mg/mL

storage temp.

2-8°C

SMILES string

CC1(C)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O

InChI

1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

InChI key

FKENQMMABCRJMK-RITPCOANSA-N

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General description

Sulbactam is a semi-synthetic penicillinate sulfone derived from 6-aminopenicllanic acid. This β-lactam compound is characterized by a β-lactam ring.

Application

Sulbactam has been used as a β-Lactamase inhibitor in β-lactamase inhibitor assay. It has also been used to evaluate its antimicrobial pharmacodynamic effects against extremely drug-resistant Acinetobacter baumannii. Sulbactam may be used in cell signaling studies.

Biochem/physiol Actions

Sulbactam acts as an irreversible inhibitor of β-lactamases that inactivate β-lactams such as penicillin and cephalosporin. It is also active against bacteroides and certain chromosomally mediated enzymes of Gram-negative bacteria. It exhibits limited antimicrobial activity. However, sulbactam in combination with other potential antibiotics exhibits therapeutic effects against multidrug-resistant Acinetobacter baumannii infections.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

S9701-10MG:
S9701-BULK:
S9701-50MG:
S9701-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
025M4733V
014M4749V
093M4721V
061M4716V

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Sarah M Drawz et al.
Clinical microbiology reviews, 23(1), 160-201 (2010-01-13)
Since the introduction of penicillin, beta-lactam antibiotics have been the antimicrobial agents of choice. Unfortunately, the efficacy of these life-saving antibiotics is significantly threatened by bacterial beta-lactamases. beta-Lactamases are now responsible for resistance to penicillins, extended-spectrum cephalosporins, monobactams, and carbapenems.
Robert K Flamm et al.
Antimicrobial agents and chemotherapy, 59(4), 2280-2285 (2015-02-04)
RX-P873 is a novel antibiotic from the pyrrolocytosine series which exhibits high binding affinity for the bacterial ribosome and broad-spectrum antibiotic properties. The pyrrolocytosines have shown in vitro activity against multidrug-resistant Gram-negative and Gram-positive strains of bacteria known to cause
Krisztina M Papp-Wallace et al.
Antimicrobial agents and chemotherapy, 56(11), 5687-5692 (2012-08-22)
Acinetobacter baumannii is an increasingly problematic pathogen in United States hospitals. Antibiotics that can treat A. baumannii are becoming more limited. Little is known about the contributions of penicillin binding proteins (PBPs), the target of β-lactam antibiotics, to β-lactam-sulbactam susceptibility
Serafim Tsitsilonis et al.
Langenbeck's archives of surgery, 398(1), 153-159 (2012-07-27)
Necrotizing fasciitis (NF) is a rare, but potentially fatal pathology. The aim of the present study was to identify the population characteristics of the NF patients, the responsible bacteria, and the differences between survivors and nonsurvivors. In this retrospective case-control
Shu Xia et al.
PloS one, 9(7), e100707-e100707 (2014-07-02)
To investigate CTX-M genotypes among extended-spectrum β-lactamase-producing Escherichia coli (ESBL-EC) isolated from patients with community-onset and hospital-onset infections in China, their clonality and the distribution of CTX-M variants in different specimens of community-onset and hospital-onset infections. ESBL-EC isolates were collected
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