Chemistry:Loracarbef

Short description: 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 (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
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 Y Key:GPYKKBAAPVOCIW-HSASPSRMSA-N Y
NY (what is this?)  (verify)

Loracarbef is an antibiotic. 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.

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.

Side effects

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

External links

• RxList.com - Loracarbef