| Revision as of 18:22, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 447601597 of page Sultamicillin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number'). |
Latest revision as of 21:17, 20 October 2024 edit 2601:642:c303:f370:55fb:d40:5db6:c77d (talk) Reclassified to Clostridioides in 2016. |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 447429128 |
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| Watchedfields = changed |
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| IUPAC_name = heptane-2-carbonyl]oxymethyl(2''R'')-6-{amino}-3,3-dimethyl-7-oxo-<br>4-thia-1-azabicycloheptane-2-carboxylate |
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| verifiedrevid = 470474605 |
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| IUPAC_name = heptane-2-carbonyl]oxymethyl(2''R'')-6-{amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate |
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| image = Sultamicillin.svg |
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| image = Sultamicillin.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Unasyn, Unacid PD oral |
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| Drugs.com = {{drugs.com|international|sultamicillin}} |
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| Drugs.com = {{drugs.com|international|sultamicillin}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = Oral |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = 80% |
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| protein_bound = |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = Mainly via kidney |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 76497-13-7 --> |
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| CAS_number = 76497-13-7 |
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| ATC_prefix = J01 |
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| ATC_prefix = J01 |
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| ATC_suffix = CR04 |
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| ATC_suffix = CR04 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 506110 |
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| ChEMBL = 506110 |
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| PubChem = 444022 |
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| PubChem = 444022 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 392048 |
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| ChemSpiderID = 392048 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 51770 |
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| ChEBI = 51770 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=25 | H=30 | N=4 | O=9 | S=2 |
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| C=25 | H=30 | N=4 | O=9 | S=2 |
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| molecular_weight = 594.659 g/mol |
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| smiles = O=C(OCOC(=O)2N1C(=O)C1S(=O)(=O)C2(C)C)4N5C(=O)(NC(=O)(c3ccccc3)N)5SC4(C)C |
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| smiles = O=C(OCOC(=O)2N1C(=O)C1S(=O)(=O)C2(C)C)4N5C(=O)(NC(=O)(c3ccccc3)N)5SC4(C)C |
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| InChI = 1/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1 |
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| InChIKey = OPYGFNJSCUDTBT-PMLPCWDUBA |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1 |
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| StdInChI = 1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1 |
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| StdInChIKey = OPYGFNJSCUDTBT-PMLPCWDUSA-N |
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| StdInChIKey = OPYGFNJSCUDTBT-PMLPCWDUSA-N |
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}} |
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}} |
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<!-- Definition and medical uses --> |
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'''Sultamicillin''', sold under the brand name '''Unasyn''' among others, is an oral form of the ] antibiotic combination ]. It is used for the treatment of bacterial infections of the upper and lower ], the kidneys and ], skin and ], among other organs. It contains ]ified ] and ].<ref name="AC">{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Unasyn-Filmtabletten |publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=de}}</ref> |
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Sultamicillin is better absorbed from the gut than ampicillin/sulbactam, decreasing the chances of ] and ]. The inclusion of sulbactam extends ampicillin's spectrum of action to ] producing strains of bacteria.<ref name="Mutschler">{{cite book| vauthors = Mutschler E |title=Arzneimittelwirkungen|language=German|location=Stuttgart|publisher=Wissenschaftliche Verlagsgesellschaft|year=2013|edition=10|pages=745, 748|isbn=978-3-8047-2898-1}}</ref> Oral sulbactam with the ] form provides a regimen of continuous sulbactam therapy throughout the treatment, resulting in better clinical results.{{fact|date=February 2021}} |
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<!-- Society and culture --> |
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It was patented in 1979 and approved for medical use in 1987.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=491 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA491 |language=en}}</ref> |
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== Medical uses == |
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{{medref|section|date=September 2014}} |
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Medical uses for sultamicillin include: |
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* Skin and soft tissue infections<ref name="AC" /> - ]s, ]s, ], ], ], ]s and abscesses caused by '']'' and '']''. |
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* ]s<ref name="AC" /> - ] and ] caused by '']'' and ''S. aureus''. Acute and chronic sinusitis caused by ''S. aureus'', '']'', '']'' and ''S. progenies''. {{clarify|date=February 2021}} ], particularly suppurative otitis media, with or without ] antrum. |
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* ]s<ref name="AC" /> - ]s,<ref name="Mutschler_therapy">{{cite book| vauthors = Mutschler E |title=Arzneimittelwirkungen|language=German|location=Stuttgart|publisher=Wissenschaftliche Verlagsgesellschaft|year=2013|edition=10|page=790|isbn=978-3-8047-2898-1}}</ref> ], ] caused by ''S. pneumoniae'', ''H. influenzae'', ''Staphylococcus aureus'' and ''S. progenies''. Acute exacerbations of ]. |
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* ]s<ref name="AC" /> - ], ] caused by '']'', '']'', '']'' and ''Staphylococcus aureus''. |
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* Surgical infections - prophylaxis and treatment of surgical site infections, peri-operative prophylaxis in orthopaedic and cardiovascular surgery. |
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* Gynecological infections - Caused by beta-lactamase producing strains of ''E. coli'' and '']'' sp. (including '']''). |
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* Infections of the ] - Bacterial ], treatment of '']'' infections as a part of MDT{{clarify|date=February 2021}} in ulcer management. |
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== Contraindications == |
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Sultamicillin is contraindicated in people with penicillin allergy and those with ], as these have an increased risk of developing severe rashes.<ref name="AC" /><ref name=="Friedel" /> |
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== Adverse effects == |
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The most common side effect, as with many other antibiotics, is ] and soft stool. In Japanese clinical trials, these occurred with a frequency of 3.7% and 1.1%, respectively; however, in studies outside Japan, diarrhoea was much more common at 10% to over 50% in patients taking sultamicillin. Other adverse effects occurring in the range of 1 to 10% of people include nausea, vomiting, stomach ache, headache, rashes, and ]. ] caused by ]s is a rare complication.<ref name="AC" /><ref name=="Friedel" /> |
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== Interactions == |
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Interactions with other drugs are similar to other penicillins: ] increases the risk for patients to develop rashes. Penicillins slow down the elimination of ], potentially increasing its adverse effects. Conversely, the elimination of sultamicillin's active constituents (ampicillin and sulbactam) is reduced by ] and probably by the ]s (NSAIDs) ], ] and ].<ref name="AC" /> |
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== Pharmacology == |
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=== Pharmacokinetics === |
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] (blue), ] (red), and the ] link (black).]] |
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Sultamicillin is a ] or (mutual ]) of ampicillin and sulbactam. After oral intake, it is absorbed and ] cleaved to ampicillin and sulbactam by ]s in the gut wall. These two substances are then released into the system in a 1:1 ] ratio. Their pharmacokinetic behaviour is similar (and practically independent of food intake): they reach peak concentrations after about one hour; their ] is 26% (ampicillin) and 29% (sulbactam); and their ] are 45–80 minutes and 40–70 minutes, respectively. Both drugs are mainly eliminated via the kidneys: within eight hours after intake, 46 to 80% of the ampicillin and 41 to 66% of the sulbactam are found in the urine.<ref name="Mutschler" /><ref name=="Friedel" /> |
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=== Mechanism of action === |
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{{see|Ampicillin#Mechanism of action|β-Lactamase inhibitor#Mechanism of action}} |
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Ampicillin, a ] orally active ] ] antibiotic, exerts antibacterial activity against sensitive organisms by inhibiting biosynthesis of cell wall mucopeptide. Sulbactam, a ], irreversibly inhibits many ]s that occur in resistant bacteria strains.<ref name="AC" /> |
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== Chemistry == |
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Ampicillin and sulbactam are linked via a ], forming two ] bonds (or more accurately ] bonds). Sultamicillin is used in form of the ] salt.<ref name="Mutschler" /><ref name=="Friedel">{{cite journal | vauthors = Friedel HA, Campoli-Richards DM, Goa KL | title = Sultamicillin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use | journal = Drugs | volume = 37 | issue = 4 | pages = 491–522 | date = April 1989 | pmid = 2661196 | doi = 10.2165/00003495-198937040-00005 | s2cid = 195693347 }}</ref> |
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== References == |
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{{Reflist}} |
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{{Cell wall disruptive antibiotics}} |
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] |
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] |
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] |
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] |