From Wikipedia, the free encyclopedia
Chemical compound
Sulbactam
AHFS /
Drugs.com
International Drug Names
MedlinePlus
a693021
Routes of administration
Intravenous ,
intramuscular
ATC code
Legal status
UK :
POM (Prescription only)
Protein binding 29%
Elimination half-life 0.65–1.20 hrs
Excretion Mainly kidneys (41–66% within 8 hrs)
(2S ,5R )-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
CAS Number
PubChem
CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.063.506
Formula C 8 H 11 N O 5 S
Molar mass 233.24 g·mol−1 3D model (
JSmol )
Melting point 148 to 151 °C (298 to 304 °F)
O=S2(=O)C([C@@H](N1C(=O)C[C@H]12)C(=O)O)(C)C
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
Y Key:FKENQMMABCRJMK-RITPCOANSA-N
Y
(verify)
Sulbactam is a
β-lactamase inhibitor . This
drug is given in combination with
β-lactam antibiotics to inhibit
β-lactamase , an
enzyme produced by
bacteria that destroys the
antibiotics .
[1]
It was patented in 1977 and approved for medical use in 1986.
[2]
Medical uses
The combination
ampicillin/sulbactam (Unasyn) is available in the United States.
[3]
The combination
cefoperazone/sulbactam (Sulperazon) is available in many countries.
[4]
The co-packaged combination
sulbactam/durlobactam was approved for medical use in the United States in May 2023.
[5]
Mechanism
Sulbactam is primarily used as a
suicide inhibitor of β-lactamase, shielding more potent beta-lactams such as ampicillin.
[6] Sulbactam itself contains a
beta-lactam ring, and has weak antibacterial activity by inhibiting
penicillin binding proteins (PBP) 1 and 3, but not 2.
[7]
References
^ Totir MA, Helfand MS, Carey MP, Sheri A, Buynak JD, Bonomo RA, Carey PR (August 2007).
"Sulbactam forms only minimal amounts of irreversible acrylate-enzyme with SHV-1 beta-lactamase" . Biochemistry . 46 (31): 8980–8987.
doi :
10.1021/bi7006146 .
PMC
2596720 .
PMID
17630699 .
^ Fischer J, Ganellin CR (2006).
Analogue-based Drug Discovery . John Wiley & Sons. p. 492.
ISBN
9783527607495 .
^
"Unasyn- ampicillin sodium and sulbactam sodium injection, powder, for solution" . DailyMed . U.S. National Library of Medicine. 29 March 2023. Retrieved 25 May 2023 .
^
"Sulperazon" .
drugs.com .
^
"FDA Approves New Treatment for Pneumonia Caused by Certain Difficult-to-Treat Bacteria" . U.S. Food and Drug Administration (Press release). 24 May 2023. Retrieved 24 May 2023 .
^ Crass RL, Pai MP (February 2019). "Pharmacokinetics and Pharmacodynamics of β-Lactamase Inhibitors". Pharmacotherapy . 39 (2): 182–195.
doi :
10.1002/phar.2210 .
PMID
30589457 .
S2CID
58567725 .
^ Penwell WF, Shapiro AB, Giacobbe RA, Gu RF, Gao N, Thresher J, et al. (March 2015).
"Molecular mechanisms of sulbactam antibacterial activity and resistance determinants in Acinetobacter baumannii" . Antimicrobial Agents and Chemotherapy . 59 (3): 1680–1689.
doi :
10.1128/AAC.04808-14 .
PMC
4325763 .
PMID
25561334 .
Further reading
Singh GS (January 2004). "Beta-lactams in the new millennium. Part-II: cephems, oxacephems, penams and sulbactam". Mini Reviews in Medicinal Chemistry . 4 (1): 93–109.
doi :
10.2174/1389557043487547 .
PMID
14754446 .