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Revision as of 18:10, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456556631 of page Sulbactam for the Chem/Drugbox validation project (updated: '').  Latest revision as of 21:24, 6 November 2024 edit Isla (talk | contribs)Extended confirmed users2,388 edits →Medical uses 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 429891367 | verifiedrevid = 470472739
| IUPAC_name = (2''S'',5''R'')-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid 4,4-dioxide | IUPAC_name = (2''S'',5''R'')-3,3-Dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid 4,4-dioxide
| image = Sulbactam.svg | image = Sulbactam.svg
| width = 150px | width = 150
| image2 = Sulbactam ball-and-stick.png

| width2 = 200
<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| Drugs.com = {{drugs.com|international|sulbactam}} | Drugs.com = {{drugs.com|international|sulbactam}}
| MedlinePlus = a693021 | MedlinePlus = a693021
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 --> | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = POM | legal_UK = POM
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status =
| routes_of_administration = Injection | routes_of_administration = ], ]

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 1 | bioavailability =
| protein_bound = | protein_bound = 29%
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life = 0.65–1.20 hrs
| excretion = Kidneys? | excretion = Mainly kidneys (41–66% within 8 hrs)

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 68373-14-8 | CAS_number = 68373-14-8
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| ATC_suffix = CG01 | ATC_suffix = CG01
| PubChem = 130313 | PubChem = 130313
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref =
| DrugBank = | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 115306 | ChemSpiderID = 115306
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08533 | KEGG = D08533
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9321 | ChEBI = 9321
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 403 | ChEMBL = 403

<!--Chemical data--> <!--Chemical data-->
| C=8 | H=11 | N=1 | O=5 | S=1 | C=8 | H=11 | N=1 | O=5 | S=1
| molecular_weight = 233.243 g/mol
| smiles = O=S2(=O)C((N1C(=O)C12)C(=O)O)(C)C | smiles = O=S2(=O)C((N1C(=O)C12)C(=O)O)(C)C
| InChI = 1/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-RITPCOANBJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FKENQMMABCRJMK-RITPCOANSA-N | StdInChIKey = FKENQMMABCRJMK-RITPCOANSA-N
| melting_point = 148
| melting_high = 151
}} }}
<!-- Definition and medical uses -->
'''Sulbactam''' is a ]. This ] is given in combination with ]s to inhibit ], an ] produced by ] that destroys the ]s.<ref name="pmid17630699">{{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 }}</ref>

<!-- Society and culture -->
It was patented in 1977 and approved for medical use in 1986.<ref name=Fis2006>{{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}}</ref>

==Medical uses==
The combination ] (Unasyn) is available in the United States.<ref>{{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}}</ref>

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

The co-packaged combination ] was approved for medical use in the United States in May 2023.<ref>{{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}}</ref>

==Mechanism==
Sulbactam is primarily used as a ] of β-lactamase, shielding more potent beta-lactams such as ampicillin.<ref>{{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 }}</ref> Sulbactam itself contains a ] ring, and has weak antibacterial activity by inhibiting ] (PBP) 1 and 3, but not 2.<ref>{{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 }}</ref>

== References ==
{{reflist}}

== Further reading ==
{{refbegin}}
* {{cite journal | vauthors = Singh GS | title = Beta-lactams in the new millennium. Part-II: cephems, oxacephems, penams and sulbactam | journal = Mini Reviews in Medicinal Chemistry | volume = 4 | issue = 1 | pages = 93–109 | date = January 2004 | pmid = 14754446 | doi = 10.2174/1389557043487547 }}
{{refend}}

{{PenicillinAntiBiotics}}

]
]
]
]

{{antibiotic-stub}}