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Sulbactam

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Sulbactam
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa693021
Routes of
administration
Intravenous,intramuscular
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding29%
Eliminationhalf-life0.65–1.20 hrs
ExcretionMainly kidneys (41–66% within 8 hrs)
Identifiers
  • (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.063.506Edit this at Wikidata
Chemical and physical data
FormulaC8H11NO5S
Molar mass233.24 g·mol−1
3D model (JSmol)
Melting point148 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 checkY
  • Key:FKENQMMABCRJMK-RITPCOANSA-N checkY
  (verify)

Sulbactam is aβ-lactamase inhibitor. Thisdrug is given in combination withβ-lactam antibiotics to inhibitβ-lactamase, anenzyme produced bybacteria that destroys theantibiotics.[1]

It was patented in 1977 and approved for medical use in 1986.[2]

Medical uses

[edit]

The combinationampicillin/sulbactam (Unasyn) is available in the United States.[3]

The combinationcefoperazone/sulbactam (Sulperazon) is available in many countries but not in the United States.[4]

The co-packaged combinationsulbactam/durlobactam was approved for medical use in the United States in May 2023.[5]

Mechanism

[edit]

Sulbactam is primarily used as asuicide inhibitor of β-lactamase, shielding more potent beta-lactams such as ampicillin.[6] Sulbactam itself contains abeta-lactam ring, and has weak antibacterial activity by inhibitingpenicillin binding proteins (PBP) 1 and 3, but not 2.[7]

References

[edit]
  1. ^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.
  2. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery. John Wiley & Sons. p. 492.ISBN 9783527607495.
  3. ^"Unasyn- ampicillin sodium and sulbactam sodium injection, powder, for solution".DailyMed. U.S. National Library of Medicine. 29 March 2023. Retrieved25 May 2023.
  4. ^"Sulperazon".drugs.com.
  5. ^"FDA Approves New Treatment for Pneumonia Caused by Certain Difficult-to-Treat Bacteria".U.S. Food and Drug Administration (Press release). 24 May 2023. Retrieved24 May 2023.
  6. ^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.
  7. ^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

[edit]
  • 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.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems /Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking:Ramoplanin§
Intracellular
Other
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