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S9701

Sigma-Aldrich

Sulbactam

Synonyme(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

Formule empirique (notation de Hill):
C8H11NO5S
Numéro CAS:
68373-14-8
Poids moléculaire :
233.24
Numéro CE :
269-878-2
Numéro MDL:
MFCD00867005
Code UNSPSC :
12352200
ID de substance PubChem :
329824632
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Niveau de qualité

100

Forme

powder

Activité optique

[α]/D ≥+225°, c = 1 in H2O

Couleur

white to tan

Solubilité

H2O: ≥18 mg/mL

Température de stockage

2-8°C

Chaîne 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

Clé InChI

FKENQMMABCRJMK-RITPCOANSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H317,H334

Classification des risques

Resp. Sens. 1 - Skin Sens. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000395626
0000308124
0000395626
0000308124
0000136152

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Consulter la Bibliothèque de documents

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.
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
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
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
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