General Information of Drug (ID: DM4L8H3)

Drug Name
Loracarbef
Synonyms
Lorabid; Loracarbefum; Lorafem; Loracarbef hydrate; KT-3777; LY-163892; Lorabid (TN); (6R,7S)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate; (6R,7S)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7S)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate; (6R,7S)-7-{[(2R)-2-ammonio-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; 7beta-[(2R)-2-amino-2-phenylacetyl]nitrilo-3-chloro-3,4-didehydrocepham-4-carboxylate; 7beta-[(2R)-2-amino-2-phenylacetyl]nitrilo-3-chloro-3,4-didehydrocepham-4-carboxylic acid; 7beta-[(2R)-2-ammonio-2-phenylacetyl]nitrilo-3-chloro-3,4-didehydrocepham-4-carboxylate
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 349.77
Logarithm of the Partition Coefficient (xlogp) -1.7
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Bioavailability
94% of drug becomes completely available to its intended biological destination(s) [3]
Elimination
94% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 1 hour [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 19.06931 micromolar/kg/day [5]
Water Solubility
The ability of drug to dissolve in water is measured as 41 mg/mL [2]
Chemical Identifiers
Formula
C16H16ClN3O4
IUPAC Name
(6R,7S)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
C1CC(=C(N2[C@H]1[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)Cl
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
Cross-matching ID
PubChem CID
5284585
ChEBI ID
CHEBI:47544
CAS Number
76470-66-1
DrugBank ID
DB00447
TTD ID
D0E9WL
VARIDT ID
DR00608

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Loracarbef (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mycophenolic acid DMRBMAU Moderate Altered absorption of Loracarbef due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [7]
Ethacrynic acid DM60QMR Moderate Increased renal excretion of Loracarbef caused by Ethacrynic acid. Essential hypertension [BA00] [8]
Furosemide DMMQ8ZG Moderate Increased renal excretion of Loracarbef caused by Furosemide. Heart failure [BD10-BD1Z] [8]
Bumetanide DMRV7H0 Moderate Increased renal excretion of Loracarbef caused by Bumetanide. Heart failure [BD10-BD1Z] [8]
Probenecid DMMFWOJ Moderate Decreased elimination of Loracarbef caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [9]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Loracarbef due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [7]
⏷ Show the Full List of 6 DDI Information of This Drug

References

1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 BDDCS applied to over 900 drugs
3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Amino acid substitutions in mosaic penicillin-binding protein 2 associated with reduced susceptibility to cefixime in clinical isolates of Neisseri... Antimicrob Agents Chemother. 2006 Nov;50(11):3638-45.
7 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
8 Chrysos G, Gargalianos P, Lelekis M, Stefanou J, Kosmidis J "Pharmacokinetic interactions of ceftazidime and frusemide." J Chemother 7 Suppl (1995): 107-10. [PMID: 8904125]
9 Brown G, Zemcov SJ, Clarke AM "Effect of probenecid on cefazolin serum concentrations." J Antimicrob Chemother 31 (1993): 1009-11. [PMID: 8360120]