Basic information
- CAS
76470-66-1- Standard SMILES
N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)c1ccccc1- InChIKey
JAPHQRWPEGVNBT-UTUOFQBUSA-N- Molecular formula
- C16H16ClN3O4
- Average molar mass
- 349.77 g/mol
- Monoisotopic mass
- 349.08293367
Overview
Loracarbef is 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. It has a role as an antimicrobial agent and an antibacterial drug. It is a conjugate acid of a loracarbef anion. It is a tautomer of a loracarbef zwitterion.
Names & identifiers
- Preferred name
- Loracarbef
- IUPAC
- (6R,7S)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Names & synonyms
loracarbef76470-66-1LorabidLoracarbefumloracarbef anhydrousAnhydrous loracarbefLorbefLORACARBEF, ANHYDROUSKT-3777W72I5ZT78ZLY163892LY-163892
Show more names
DTXSID7023223CHEBI:47544(6R,7S)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid1-Azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2R)-aminophenylacetyl)amino)-3-chloro-8-oxo-, (6R,7S)-1-Azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((aminophenylacetyl)amino)-3-chloro-8-oxo-, (6R-(6alpha,7beta(R*)))-(6R,7S)-7-((2R)-2-amino-2-phenylacetamido)-3-chloro-8-oxo-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:800042DTXCID503223
Database identifiers
- CAS
76470-66-1- PubChem CID
- 5284585
- DTXSID
DTXSID7023223- ChEMBL
CHEMBL1013、CHEMBL1200610- ChEBI
CHEBI:47544- UNII
- W72I5ZT78Z
- Nikkaji
- J362.169C
Properties
Computed structural properties
- XLogP
- -1.7
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 600
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
LogP0.5
Solubility3.25e-01 g/L
Human Drugs
Breast Feeding; Lactation; Anti-Infective Agents; Antibacterial Agents; Carbacephems;
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Loracarbef
vLess-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding25%
Pharmacodynamics
Loracarbef is considered a second generation cephalosporin antibiotic. The advantages of cephalosporin antibiotics include a broad range of activity, a safe record in children with almost no dose-related toxicity, and the lack of need to monitor levels. Adverse reactions are rare and consist primarily of hypersensitivity reactions with urticaria, nonspecific rash, and pruritus. Loracarbef can be used to treat a large number of bacterial infections caused by gram-negative and gram-positive bacteria, including upper respiratory tract bacterial infections, chronic bronchitis, pneumonia, sinusitis, pharyntitis and tonsillitis, skin absceses, urinary tract infections and pyelonephritis caused by <i>E. coli</i>, <i>S. pyogenes</i>, <i>S. aureus</i>, <i>S. saprphyticus</i>, <i>S. penumoniae</i>, <i>H. influenzae</i> and <i>M. catarrhalis</i>.
Mechanism of Action
Loracarbef is an oral, synthetic beta-lactam antibiotic of the carbacephem class. Chemically, carbacephems differ from cephalosporin-class antibiotics in the dihydrothiazine ring where a methylene group has been substituted for a sulfur atom. Loracarbef has a spectrum of activity similar to that of the second generation cephalosporins. It is structurally identical to cefaclor except for a sulfur atom that has been replaced by a methylene group. This change gives greater chemical stability in solution and allows storage at room temperature. Loracarbef, like all b-lactams and cephalosporins, inhibits penicillin binding proteins, enzymes that create the cross-linkage of the peptidoglycan polymer. This binding leads to interference with the formation and remodeling of the cell wall structure.
Biological Half-Life1 hour. In subjects with moderate impairment of renal function the plasma half-life was prolonged to approximately 5.6 hours.
Metabolism/MetabolitesThere is no evidence of metabolism in humans.
FDA Pharmacological Classification
W72I5ZT78Z
LORACARBEF ANHYDROUS
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Loracarbef anhydrous is a Cephalosporin Antibacterial.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionWell absorbed with approximately 90% absorbed from the gastrointestinal tract after oral ingestion.
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >50
Related reactions
8 records
Compound notes
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