Sultamicillin: Difference between revisions

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⚫	\| verifiedrevid = ~~401071385~~
	\| IUPAC_name = heptane-2-carbonyl]oxymethyl(2''R'')-6-{amino}-3,3-dimethyl-7-oxo-<br>4-thia-1-azabicycloheptane-2-carboxylate		\| IUPAC_name = heptane-2-carbonyl]oxymethyl(2''R'')-6-{amino}-3,3-dimethyl-7-oxo-<br>4-thia-1-azabicycloheptane-2-carboxylate
	\| image = Sultamicillin.svg		\| image = Sultamicillin.svg
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	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 392048		\| ChemSpiderID = 392048
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	\| KEGG_Ref = {{keggcite\|~~changed~~\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D05972		\| KEGG = D05972
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	\| ChEBI = 51770		\| ChEBI = 51770

Revision as of 04:10, 31 August 2011

Pharmaceutical compound

Sultamicillin
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	J01CR04 (WHO)
Identifiers
IUPAC name heptane-2-carbonyl]oxymethyl(2R)-6-{amino}-3,3-dimethyl-7-oxo- 4-thia-1-azabicycloheptane-2-carboxylate
CAS Number	76497-13-7
PubChem CID	444022
ChemSpider	392048
UNII	65DT0ML581
KEGG	D05972
ChEBI	CHEBI:51770
CompTox Dashboard (EPA)	DTXSID501010077
Chemical and physical data
Formula	C₂₅H₃₀N₄O₉S₂
Molar mass	594.659 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(OCOC(=O)2N1C(=O)C1S(=O)(=O)C2(C)C)4N5C(=O)(NC(=O)(c3ccccc3)N)5SC4(C)C
InChI InChI=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 Key:OPYGFNJSCUDTBT-PMLPCWDUSA-N
(verify)

Sultamicillin is an oral form of the antibiotic combination (codrug or mutual prodrug) ampicillin/sulbactam. It contains esterified ampicillin and sulbactam and is marketed under a number of trade names, including Saltum and Unasyn

Singh GS. Beta-lactams in the new millennium. Part-II: cephems, oxacephems, penams and sulbactam.

Mini Rev Med Chem. 2004 Jan;4(1):93-109. Review. 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)

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

Aminopenicillins (3rd generation)	Amoxicillin Ampicillin (Pivampicillin Hetacillin Bacampicillin Lenampicillin Metampicillin Talampicillin) Epicillin
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin / Carindacillin Temocillin
Ureidopenicillins (4th generation)	Piperacillin Azlocillin Mezlocillin
Other	Mecillinam (Pivmecillinam) Sulbenicillin

1st generation	Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefonicid Ceforanide Cefuzonam Cephamycin (Cefoxitin Cefotetan Cefminox Cefbuperazone Cefmetazole) Carbacephem (Loracarbef)
3rd generation	Cefixime Ceftriaxone Cefotaxime Antipseudomonal (Ceftazidime Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem (Flomoxef Latamoxef)
4th generation	Cefepime Cefozopran Cefpirome Cefquinome
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol
Veterinary	Ceftiofur Cefquinome Cefovecin

Combinations

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

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