Loracarbef: Difference between revisions

Loracarbef
Clinical data
Trade names	Lorabid
AHFS/Drugs.com	Monograph
MedlinePlus	a601206
ATC code	J01DC08 (WHO) ;
Pharmacokinetic data
Protein binding	25%
Identifiers
	IUPAC name (6R,7S)-7-[[(2S)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	76470-66-1 ;
PubChem CID	5284584;
DrugBank	DB00447 ;
ChemSpider	4447634 ;
UNII	W72I5ZT78Z;
KEGG	D08143 ;
ChEMBL	ChEMBL1013 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C16H16ClN3O4
Molar mass	349.769 g/mol
3D model (JSmol)	Interactive image;
	SMILES Cl\C3=C(/C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]2CC3.O;
	InChI InChI=1S/C16H16ClN3O4.H2O/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8;/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24);1H2/t10-,11-,12+;/m1./s1 ; Key:GPYKKBAAPVOCIW-HSASPSRMSA-N = = ;
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Revision as of 03:27, 31 December 2013

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Loracarbef is a synthetic carbacephem antibiotic.^[1] Loracarbef has a spectrum of activity similar to that of the second generation cephalosporins. It is an analogue of cefaclor from which the sulfur atom is replaced with a methylene group. Therefore loracarbef has a greater stability in solution and may be stored at room temperature.

Diarrhea is the most common adverse effect. Side effects are more frequently seen with children under the age of twelve. It received FDA approval in 1991. Its use was discontinued in 2006.

US Brand Names

LORABID^®

Mechanism of Action

Loracarbef is an oral, synthetic beta-lactam antibiotic of the carbacephem class. Loracarbef, like all beta-lactams and cephalosporins, inhibits penicillin binding proteins, enzymes that create the cross-linkage of the peptidoglycan polymer. This binding leads to interference with the formation and remodeling of the cell wall structure.

References

↑ Biedenbach DJ, Jones RN (1994). "Predictive accuracy of disk diffusion test for Proteus vulgaris and Providencia species against five newer orally administered cephalosporins, cefdinir, cefetamet, cefprozil, cefuroxime, and loracarbef". J. Clin. Microbiol. 32 (2): 559–62. PMC 263078. PMID 8150976. Unknown parameter |month= ignored (help)

External links

RxList.com - Loracarbef

[pmid8150976-1] Biedenbach DJ, Jones RN (1994). "Predictive accuracy of disk diffusion test for Proteus vulgaris and Providencia species against five newer orally administered cephalosporins, cefdinir, cefetamet, cefprozil, cefuroxime, and loracarbef". J. Clin. Microbiol. 32 (2): 559–62. PMC 263078. PMID 8150976. Unknown parameter |month= ignored (help)

[1]

@@ Line 53: / Line 53: @@
 ==Overview==
-Loracarbef is an [[antibiotic]].<ref name="pmid8150976">{{cite journal |author=Biedenbach DJ, Jones RN |title=Predictive accuracy of disk diffusion test for Proteus vulgaris and Providencia species against five newer orally administered cephalosporins, cefdinir, cefetamet, cefprozil, cefuroxime, and loracarbef |journal=J. Clin. Microbiol. |volume=32 |issue=2 |pages=559–62 |year=1994 |month=February |pmid=8150976 |pmc=263078 |doi= |url=http://jcm.asm.org/cgi/pmidlookup?view=long&pmid=8150976}}</ref> Its use was discontinued in 2006.{{fact|date=January 2011}} It is a [[carbacephem]], but it is sometimes grouped together with the second-generation [[cephalosporin]] antibiotics. It was marketed under the trade name Lorabid.
+Loracarbef is a synthetic [[carbacephem]] antibiotic.<ref name="pmid8150976">{{cite journal |author=Biedenbach DJ, Jones RN |title=Predictive accuracy of disk diffusion test for Proteus vulgaris and Providencia species against five newer orally administered cephalosporins, cefdinir, cefetamet, cefprozil, cefuroxime, and loracarbef |journal=J. Clin. Microbiol. |volume=32 |issue=2|pages=559–62 |year=1994 |month=February |pmid=8150976 |pmc=263078 |doi= |url=http://jcm.asm.org/cgi/pmidlookup?view=long&pmid=8150976}}</ref> Loracarbef has a spectrum of activity similar to that of the second generation [[cephalosporin]]s. It is an analogue of [[cefaclor]] from which the [[sulfur]] atom is replaced with a [[methylene]] group. Therefore loracarbef has a greater stability in solution and may be stored at room temperature.
-Loracarbef is a synthetic "carba" analogue of cefaclor, and is more stable chemically. Diarrhea is the most common adverse effect with Loracarbef. Side effects are more frequently seen with children under the age of twelve. It received FDA approval in 1991.
+[[Diarrhea]] is the most common adverse effect. Side effects are more frequently seen with children under the age of twelve. It received FDA approval in 1991. Its use was discontinued in 2006.
 ==Category==