Loracarbef: Difference between revisions

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{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 462093698
| IUPAC_name = (6''R'',7''S'')-7-<nowiki>[[</nowiki>(2''S'')-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
| image = Loracarbef.png
<!--Clinical data-->
| tradename = Lorabid
| Drugs.com = {{drugs.com|monograph|loracarbef}}
| MedlinePlus = a601206
| pregnancy_category = 
| legal_status = 
| routes_of_administration = 
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 25%
| metabolism = 
| elimination_half-life = 
<!--Identifiers-->
| CASNo_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 76470-66-1
| ATC_prefix = J01
| ATC_suffix = DC08
| PubChem = 5284584
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00447
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4447634
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = W72I5ZT78Z
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08143
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1013
<!--Chemical data-->
| C=16 | H=16 | Cl=1 | N=3 | O=4
| molecular_weight = 349.769 g/mol
| smiles = Cl\C3=C(/C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]2CC3.O
| InChI = 1/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
| InChIKey = GPYKKBAAPVOCIW-HSASPSRMBZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}= {{stdinchicite|correct|chemspider}}= {{stdinchicite|correct|chemspider}}
| StdInChIKey = GPYKKBAAPVOCIW-HSASPSRMSA-N
}}
__NOTOC__
__NOTOC__
{{CMG}}
{{CMG}}


==Overview==
==Overview==
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 [[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.


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==Category==
==Category==
Carbacephem
Carbacephem


==US Brand Names==
==Brand Names==
 
LORABID<sup>®</sup>
LORABID<sup>®</sup>


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==References==
==References==
{{Reflist|2}}
{{Reflist|2}}
==External links==
* [http://www.rxlist.com/cgi/generic/loracarb.htm RxList.com - Loracarbef]


[[Category:Antibiotics]]
[[Category:Antibiotics]]
[[Category:Wikinfect]]
[[Category:Wikinfect]]

Revision as of 22:01, 5 January 2014

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.

Category

Carbacephem

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

  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)