loracarbef

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 462093698

| 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

| image = Loracarbef.svg

| tradename = Lorabid

| Drugs.com = {{drugs.com|monograph|loracarbef}}

| MedlinePlus = a601206

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound = 25%

| metabolism =

| elimination_half-life =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 76470-66-1

| ATC_prefix = J01

| ATC_suffix = DC08

| PubChem = 5284584

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00447

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4447634

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = W72I5ZT78Z

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08143

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1013

| C=16 | H=16 | Cl=1 | N=3 | O=4

| smiles = Cl\C3=C(/C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]2CC3.O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GPYKKBAAPVOCIW-HSASPSRMSA-N

}}

Loracarbef is an antibiotic.{{cite journal | vauthors = Biedenbach DJ, Jones RN | title = 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 = Journal of Clinical Microbiology | volume = 32 | issue = 2 | pages = 559–62 | date = February 1994 | pmid = 8150976 | pmc = 263078 | doi = 10.1128/JCM.32.2.559-562.1994}} 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.{{fact|date=January 2011}}

Usage & indications

Loracarbef was used to treat infections of the lungs, maxillary sinuses, throat, skin, and urinary tract.{{Cite web|title=Lorabid (Loracarbef): Uses, Dosage, Side Effects, Interactions, Warning|url=https://www.rxlist.com/lorabid-drug.htm|access-date=2020-06-15|website=RxList|language=en}}

= 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. saprophyticus, S. pneumoniae, H. influenzae and M. catarrhalis. {{Cite web|title=Loracarbef|url=https://www.drugbank.ca/drugs/DB00447|access-date=2020-06-15|website=www.drugbank.ca}}

Side effects

Diarrhea is the most common adverse effect with loracarbef. Side effects are more frequently seen with children under the age of twelve.{{cn|date=January 2023}}

References

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