Loracarbef

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.

Loracarbef
Clinical data
Trade namesLorabid
AHFS/Drugs.comMonograph
MedlinePlusa601206
ATC code
Pharmacokinetic data
Protein binding25%
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H16ClN3O4
Molar mass349.77 g·mol−1
3D model (JSmol)
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
 NY (what is this?)  (verify)

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
  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.
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