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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

Pureté

≥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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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.
Bahadir M Gulluoglu et al.
Annals of surgery, 257(1), 37-43 (2012-09-25)
To assess the impact of prophylactic antibiotics on the prevention of surgical site infection (SSI) and the cost-effectiveness of this prophylaxis for breast cancer surgery in overweight or obese women. SSI is higher than expected after breast surgery. Obesity was
G S Singh
Mini reviews in medicinal chemistry, 4(1), 93-109 (2004-02-03)
Beta-lactam ring-containing compounds such as penicillins, ampicillin, amoxicillin, cephalosporins and carbapenems are among the most famous antibiotics. This article reviews the recent developments in study of cephems, oxacephems, penams and sulbactam. Many of the compounds reviewed have potential antibacterial activity
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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