Loracarbef (original) (raw)

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Chemical compound

Loracarbef
Clinical data
Trade names Lorabid
AHFS/Drugs.com Monograph
MedlinePlus a601206
ATC code J01DC08 (WHO)
Pharmacokinetic data
Protein binding 25%
Identifiers
IUPAC name (6_R_,7_S_)-7-[[(2_S_)-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 checkY
PubChem CID 5284584
DrugBank DB00447 checkY
ChemSpider 4447634 checkY
UNII W72I5ZT78Z
KEGG D08143 checkY
ChEMBL ChEMBL1013 ☒N
CompTox Dashboard (EPA) DTXSID7023223 Edit this at Wikidata
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 checkYKey:GPYKKBAAPVOCIW-HSASPSRMSA-N checkY
☒NcheckY (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.

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

Usage & indications

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

Spectrum of activity

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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. saprophyticus, S. pneumoniae, H. influenzae and M. catarrhalis. [3]

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

  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.