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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-7-oxo-6--4-thia-1-azabicycloheptane-2-carboxylic acid |
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| Watchedfields = changed |
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| image = Sulbenicillin.svg |
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| verifiedrevid = 408887617 |
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| CAS_number = 41744-40-5 |
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| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-7-oxo-6--4-thia-1-azabicycloheptane-2-carboxylic acid |
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| CAS_supplemental = {{CAS|28002-18-8}} (disodium salt) |
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| image = Sulbenicillin.svg |
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| ATC_prefix = J01 |
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| ATC_suffix = CA16 |
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<!--Clinical data--> |
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| ATC_supplemental = |
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| tradename = |
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| PubChem = 39031 |
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| Drugs.com = {{drugs.com|international|sulbenicillin}} |
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| DrugBank = |
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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_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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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, or Class A, B, C --> |
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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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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 41744-40-5 |
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| CAS_supplemental = {{CAS|28002-18-8}} |
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| ATC_prefix = J01 |
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| ATC_suffix = CA16 |
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| ATC_supplemental = |
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| PubChem = 39031 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = Q2VYF0562D |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D08534 |
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| KEGG = D08534 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| chemical_formula = |
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| ChEMBL = 564107 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 16736045 |
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<!--Chemical data--> |
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| chemical_formula = |
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| C=16 | H=18 | N=2 | O=7 | S=2 |
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| C=16 | H=18 | N=2 | O=7 | S=2 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| molecular_weight = 414.45 g/mol |
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| StdInChI = 1S/C16H18N2O7S2/c1-16(2)11(15(21)22)18-13(20)9(14(18)26-16)17-12(19)10(27(23,24)25)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,17,19)(H,21,22)(H,23,24,25)/t9-,10-,11+,14-/m1/s1 |
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| bioavailability = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| protein_bound = |
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| StdInChIKey = JETQIUPBHQNHNZ-NJBDSQKTSA-N |
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| metabolism = |
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| SMILES = CC1((N2(S1)(C2=O)NC(=O)(c3ccccc3)S(=O)(=O)O)C(=O)O)C |
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| elimination_half-life = |
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| excretion = |
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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_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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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, or Class A, B, C --> |
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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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| routes_of_administration = |
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}} |
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}} |
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'''Sulbenicillin''' (]) is a ] ], notable for its combination use with ]. <ref name="pmid3114912">{{cite journal |vauthors=Aonuma S, Ariji F, Oizumi K, Konno K |date=June 1987 |title=Electron microscopy of Pseudomonas aeruginosa treated with sulbenicillin and dibekacin |url=https://www.jstage.jst.go.jp/article/tjem1920/152/2/152_2_119/_article |journal=Tohoku J. Exp. Med. |volume=152 |issue=2 |pages=119–28 |doi=10.1620/tjem.152.119 |pmid=3114912 |doi-access=free}}</ref> ], crucial in primary ] for potent ] properties and wide distribution, include oral options for enhanced accessibility. Post-], synthetic penicillins like sulbenicillin broadened efficacy, leading to new groups that diversified treatment. This evolution reflects a dynamic interplay between ] and clinical needs, emphasizing enduring value in managing infectious diseases in ]. |
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'''Sulbenicillin''' (]) is a ] ]. |
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== Structure and mechanism of action == |
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It has been used in combination with ].<ref name="pmid3114912">{{cite journal |author=Aonuma S, Ariji F, Oizumi K, Konno K |title=Electron microscopy of Pseudomonas aeruginosa treated with sulbenicillin and dibekacin |journal=Tohoku J. Exp. Med. |volume=152 |issue=2 |pages=119–28 |year=1987 |month=June |pmid=3114912 |doi= 10.1620/tjem.152.119|url=http://joi.jlc.jst.go.jp/JST.Journalarchive/tjem1920/152.119?from=PubMed |format={{dead link|date=May 2010}}}}</ref> |
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Characterized by a distinctive beta-lactam ring, penicillins inhibit bacterial cell wall synthesis, leading to cell destruction. This mechanism is effective against a broad spectrum of bacteria.<ref>{{Cite web |last=PubChem |title=CID 5317 |url=https://pubchem.ncbi.nlm.nih.gov/compound/5317 |access-date=2023-12-20 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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{{antibiotic-stub}} |
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{{PenicillinAntiBiotics}} |
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{{PenicillinAntiBiotics}} |
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] |
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] |
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] |
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{{antibiotic-stub}} |