CHEBI:47544 - loracarbef

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ChEBI Name loracarbef
ChEBI ID CHEBI:47544
Definition A synthetic "carba" analogue of cefaclor, with carbon replacing sulfur at position 1. Used to treat a wide range of infections caused by both gram-positive and gram-negative bacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H16ClN3O4
Net Charge 0
Average Mass 349.76900
Monoisotopic Mass 349.083
InChI InChI=1S/C16H16ClN3O4/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)/t10-,11-,12+/m1/s1
InChIKey JAPHQRWPEGVNBT-UTUOFQBUSA-N
SMILES N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)c1ccccc1
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
antibacterial drug
A drug used to treat or prevent bacterial infections.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
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ChEBI Ontology
Outgoing loracarbef (CHEBI:47544) has role antibacterial drug (CHEBI:36047)
loracarbef (CHEBI:47544) has role antimicrobial agent (CHEBI:33281)
loracarbef (CHEBI:47544) is a carbacephem (CHEBI:55504)
loracarbef (CHEBI:47544) is conjugate acid of loracarbef anion (CHEBI:281056)
loracarbef (CHEBI:47544) is tautomer of loracarbef zwitterion (CHEBI:214480)
Incoming loracarbef anion (CHEBI:281056) is conjugate base of loracarbef (CHEBI:47544)
loracarbef zwitterion (CHEBI:214480) is tautomer of loracarbef (CHEBI:47544)
IUPAC Names
(6R,7S)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7β-[(2R)-2-amino-2-phenylacetyl]nitrilo-3-chloro-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
loracarbef ChemIDplus
loracarbefum ChemIDplus
Synonym Source
LORACABEF PDBeChem
Manual Xrefs Databases
1603 DrugCentral
D08143 KEGG DRUG
DB00447 DrugBank
EP14476 Patent
HMDB0014590 HMDB
LOR PDBeChem
LSM-5429 LINCS
US4708956 Patent
View more database links
Registry Numbers Types Sources
3631282 Beilstein Registry Number Beilstein
3631282 Reaxys Registry Number Reaxys
76470-66-1 CAS Registry Number ChemIDplus
76470-66-1 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
1553350 PubMed citation Europe PMC
1621740 PubMed citation Europe PMC
1621742 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
8453172 PubMed citation Europe PMC
9131470 PubMed citation Europe PMC
Last Modified
09 February 2018