Loracarbef

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 Y
PubChem CID	5284584
DrugBank	DB00447 Y
ChemSpider	4447634 Y
UNII	W72I5ZT78Z
KEGG	D08143 Y
ChEMBL	ChEMBL1013 N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
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 Y Key:GPYKKBAAPVOCIW-HSASPSRMSA-N Y=  Y=  Y
NY (what is this?)  (verify)

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List of terms related to Loracarbef

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

Overview

Loracarbef is a synthetic carbacephem antibiotic. 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^® (DISCONTINUED)

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.