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S9701

Sigma-Aldrich

Sulbactam

Synonim(y):

(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

Wzór empiryczny (zapis Hilla):
C8H11NO5S
Numer CAS:
68373-14-8
Masa cząsteczkowa:
233.24
Numer WE:
269-878-2
Numer MDL:
MFCD00867005
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
329824632
NACRES:
NA.77

Próba

≥98% (HPLC)

Postać

powder

aktywność optyczna

[α]/D ≥+225°, c = 1 in H2O

kolor

white to tan

rozpuszczalność

H2O: ≥18 mg/mL

temp. przechowywania

2-8°C

ciąg SMILES

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

Klucz InChI

FKENQMMABCRJMK-RITPCOANSA-N

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Opis ogólny

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

Zastosowanie

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.

Działania biochem./fizjol.

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.
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Piktogramy

Health hazard
GHS08

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H317,H334

Zwroty wskazujące środki ostrożności

P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313

Klasyfikacja zagrożeń

Resp. Sens. 1 - Skin Sens. 1

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Certyfikaty analizy (CoA)

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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
A S Levin
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 8(3), 144-153 (2002-05-16)
Recent studies have highlighted the emergence of infections involving multiresistant Acinetobacter clinical isolates. Sulbactam offers direct antimicrobial activity against Acinetobacter species. Accordingly, co-administration of sulbactam with ampicillin or cefoperazone offers the potential of effective empirical therapy against Acinetobacter and other
Mei Li et al.
Antimicrobial agents and chemotherapy, 56(11), 5678-5686 (2012-08-22)
Ambler position 105 in class A β-lactamases is implicated in resistance to clavulanic acid, although no clinical isolates with mutations at this site have been reported. We hypothesized that Y105 is important in resistance to clavulanic acid because changes in
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