Bacampicillin: Difference between revisions

Revision as of 23:00, 22 October 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - updated 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or [[u...← Previous edit		Revision as of 15:23, 4 November 2011 edit undoBeetstra (talk \| contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI', 'StdInChI', 'StdInChIKey', 'CAS_number').Next edit →
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	<!--Identifiers-->		<!--Identifiers-->
	\| CAS_number_Ref = {{cascite\|correct\|??}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 37661-08-8		\| CAS_number = <!-- blanked - oldvalue: 37661-08-8 -->
	\| ATC_prefix = J01		\| ATC_prefix = J01
	\| ATC_suffix = CA06		\| ATC_suffix = CA06
	\| ATC_supplemental =		\| ATC_supplemental =
			\| ChEBI = 2968
			\| StdInChI = 1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
			\| StdInChIKey = PFOLLRNADZZWEX-FFGRCDKISA-N
	\| PubChem = 39849		\| PubChem = 39849
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank =		\| DrugBank = DB01602
	\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| ChemSpiderID = 390135		\| ChemSpiderID = 390135

Revision as of 15:23, 4 November 2011

Pharmaceutical compound

Bacampicillin
Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral
ATC code	J01CA06 (WHO)
Pharmacokinetic data
Metabolism	Rapidly hydrolyzed to ampicillin
Identifiers
IUPAC name 1-Ethoxycarbonyloxyethyl (2S,5R)-6-amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylate
PubChem CID	39849
DrugBank	DB01602
ChemSpider	390135
UNII	8GM2J22278
ChEBI	CHEBI:2968
ChEMBL	ChEMBL1583
CompTox Dashboard (EPA)	DTXSID2048030
Chemical and physical data
Formula	C₂₁H₂₇N₃O₇S
Molar mass	465.519 g/mol g·mol
InChI InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1 Key:PFOLLRNADZZWEX-FFGRCDKISA-N
(what is this?) (verify)

Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.

It is sold under the brand names Spectrobid (Pfizer) and Penglobe (AstraZeneca).

Bodin NO; Ekström B; Forsgren U; et al. (1975). "Bacampicillin: a New Orally Well-Absorbed Derivative of Ampicillin". Antimicrob Agents Chemother. 8 (5): 518–25. PMC 429411. PMID 1211909. {{cite journal}}: Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)

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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