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Merck
CN

S9701

Sigma-Aldrich

Sulbactam

≥98% (HPLC), β-lactamases inhibitor, powder

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

Key Documents

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Product Name

Sulbactam,

Assay

98-102% (HPLC)

form

crystalline powder

color

white to off-white

solubility

H2O: 1%

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 Information

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

Lot/Batch Number
0000308127
0000308127
0000452398
0000452398
0000431502

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Mallika Sengupta et al.
Cureus, 14(2), e21802-e21802 (2022-03-08)
Background Acinetobacter species are known to be important hospital-acquired pathogens. Unfortunately, multidrug-resistant Acinetobacter spp. has very limited options for an effective treatment. Aim To identify the common pathogens causing lower respiratory tract infections (LRTI), their antimicrobial susceptibility pattern, and determine the minimum inhibitory
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.
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
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
J D Williams
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 24(3), 494-497 (1997-03-01)
beta-Lactamase inhibitors such as sulbactam are beta-lactam compounds that have low antimicrobial activity but are able to inhibit enzymes (beta-lactamases) that destroy beta-lactam antibiotics like penicillins and cephalosporins. The main activity of beta-lactamase inhibitors is directed against plasmid-mediated transferable enzymes
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