sulbactam

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 470472739

| IUPAC_name = (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide

| image = Sulbactam.svg

| image_class = skin-invert-image

| width = 150

| image2 = Sulbactam ball-and-stick.png

| image_class2 = bg-transparent

| width2 = 200

| tradename =

| Drugs.com = {{drugs.com|international|sulbactam}}

| MedlinePlus = a693021

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK = POM

| legal_US =

| legal_status =

| routes_of_administration = Intravenous, intramuscular

| bioavailability =

| protein_bound = 29%

| metabolism =

| elimination_half-life = 0.65–1.20 hrs

| excretion = Mainly kidneys (41–66% within 8 hrs)

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 68373-14-8

| ATC_prefix = J01

| ATC_suffix = CG01

| PubChem = 130313

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 115306

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S4TF6I2330

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08533

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 9321

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 403

| C=8 | H=11 | N=1 | O=5 | S=1

| smiles = O=S2(=O)C([C@@H](N1C(=O)C[C@H]12)C(=O)O)(C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FKENQMMABCRJMK-RITPCOANSA-N

| melting_point = 148

| melting_high = 151

}}

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.{{cite journal | vauthors = Totir MA, Helfand MS, Carey MP, Sheri A, Buynak JD, Bonomo RA, Carey PR | title = Sulbactam forms only minimal amounts of irreversible acrylate-enzyme with SHV-1 beta-lactamase | journal = Biochemistry | volume = 46 | issue = 31 | pages = 8980–8987 | date = August 2007 | pmid = 17630699 | pmc = 2596720 | doi = 10.1021/bi7006146 }}

It was patented in 1977 and approved for medical use in 1986.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=492 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA492 |language=en}}

Medical uses

The combination ampicillin/sulbactam (Unasyn) is available in the United States.{{cite web | title=Unasyn- ampicillin sodium and sulbactam sodium injection, powder, for solution | work = DailyMed | publisher = U.S. National Library of Medicine | date=29 March 2023 | url= https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=12eeb72a-403d-41be-bae4-4cb930862884 | access-date=25 May 2023}}

The combination cefoperazone/sulbactam (Sulperazon) is available in many countries but not in the United States.{{Cite web | url = https://www.drugs.com/international/sulperazon.html | title = Sulperazon | publisher = drugs.com }}

The co-packaged combination sulbactam/durlobactam was approved for medical use in the United States in May 2023.{{cite press release | title=FDA Approves New Treatment for Pneumonia Caused by Certain Difficult-to-Treat Bacteria | website=U.S. Food and Drug Administration | date=24 May 2023 | url=https://www.fda.gov/news-events/press-announcements/fda-approves-new-treatment-pneumonia-caused-certain-difficult-treat-bacteria | access-date=24 May 2023}}

Mechanism

Sulbactam is primarily used as a suicide inhibitor of β-lactamase, shielding more potent beta-lactams such as ampicillin.{{cite journal | vauthors = Crass RL, Pai MP | title = Pharmacokinetics and Pharmacodynamics of β-Lactamase Inhibitors | journal = Pharmacotherapy | volume = 39 | issue = 2 | pages = 182–195 | date = February 2019 | pmid = 30589457 | doi = 10.1002/phar.2210 | s2cid = 58567725 }} Sulbactam itself contains a beta-lactam ring, and has weak antibacterial activity by inhibiting penicillin binding proteins (PBP) 1 and 3, but not 2.{{cite journal | vauthors = Penwell WF, Shapiro AB, Giacobbe RA, Gu RF, Gao N, Thresher J, McLaughlin RE, Huband MD, DeJonge BL, Ehmann DE, Miller AA | display-authors = 6 | title = Molecular mechanisms of sulbactam antibacterial activity and resistance determinants in Acinetobacter baumannii | journal = Antimicrobial Agents and Chemotherapy | volume = 59 | issue = 3 | pages = 1680–1689 | date = March 2015 | pmid = 25561334 | pmc = 4325763 | doi = 10.1128/AAC.04808-14 }}

sulbactam

Medical uses

Mechanism

References

Further reading