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S9701

Sigma-Aldrich

Sulbactam

Synonym(e):

(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsäure-4,4-dioxid, Betamaze, CP 45899, CP-45,899, Penicillansäure-1,1-dioxid, Penicillansäure-S,S-dioxid, Penicillansäuredioxid, Penicillansäuresulfon

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About This Item

Empirische Formel (Hill-System):
C8H11NO5S
CAS-Nummer:
68373-14-8
Molekulargewicht:
233.24
EG-Nummer:
269-878-2
MDL-Nummer:
MFCD00867005
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329824632
NACRES:
NA.77

Assay

≥98% (HPLC)

Qualitätsniveau

100

Form

powder

Optische Aktivität

[α]/D ≥+225°, c = 1 in H2O

Farbe

white to tan

Löslichkeit

H2O: ≥18 mg/mL

Lagertemp.

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

InChIKey

FKENQMMABCRJMK-RITPCOANSA-N

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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Piktogramme

Health hazard
GHS08

Signalwort

Danger

H-Sätze

H317,H334

Gefahreneinstufungen

Resp. Sens. 1 - Skin Sens. 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (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.
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
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
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
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