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 ;
PubChem CID	5284584;
DrugBank	DB00447 ;
ChemSpider	4447634 ;
UNII	W72I5ZT78Z;
KEGG	D08143 ;
ChEMBL	ChEMBL1013 ;
CompTox Dashboard (EPA)	DTXSID7023223 ;
Chemical and physical data
Formula	C16H16ClN3O4
Molar mass	349.77 g·mol−1
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 ;
	(what is this?) (verify)

Loracarbef is an antibiotic.[1] It is a carbacephem, but it is sometimes grouped together with the second-generation cephalosporin antibiotics. Loracarbef is a synthetic "carba" analog of cefaclor, and is more stable.

History

Loracarbef received FDA approval in 1991 and it was marketed under the trade name Lorabid. Its use was discontinued in 2006.

Usage & Indications

Loracarbef was used to treat infections of the lungs, maxillary sinuses, throat, skin, and urinary tract.[2]

Spectrum of Activity

Loracarbef had broad spectrum effectiveness against both gram-negative and gram-positive bacteria, including those precipitating infections of the respiratory tract, sinuses, tonsils, skin, urinary tract, and kidneys. It was of specific use in those infections caused by E. Coli, S. pyogenes, S. Aureus, S. saprphyticus, S. penumoniae, H. influenza, and M. catarrhalis. [3]

Side effects

Diarrhea is the most common adverse effect with loracarbef. Side effects are more frequently seen with children under the age of twelve.

References

Biedenbach DJ, Jones RN (February 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". Journal of Clinical Microbiology. 32 (2): 559–62. doi:10.1128/JCM.32.2.559-562.1994. PMC 263078. PMID 8150976.
"Lorabid (Loracarbef): Uses, Dosage, Side Effects, Interactions, Warning". RxList. Retrieved 2020-06-15.
"Loracarbef". www.drugbank.ca. Retrieved 2020-06-15.

External links

RxList.com - Loracarbef

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[pmid8150976-1] Biedenbach DJ, Jones RN (February 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". Journal of Clinical Microbiology. 32 (2): 559–62. doi:10.1128/JCM.32.2.559-562.1994. PMC 263078. PMID 8150976.

[2] "Lorabid (Loracarbef): Uses, Dosage, Side Effects, Interactions, Warning". RxList. Retrieved 2020-06-15.

[3] "Loracarbef". www.drugbank.ca. Retrieved 2020-06-15.