Details of the Drug

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

Affected Organisms

Various gram-negative and gram-positive eubacteriaStaphylococcus aureusStreptococcus pneumoniaeStreptococcus pyogenesHaemophilus influenzaeEscherichia coli

ATC Code

J01DC08: Loracarbef

J01DC: Second-generation cephalosporins

J01D: OTHER BETA-LACTAM ANTIBACTERIALS

J01: ANTIBACTERIALS FOR SYSTEMIC USE

J: ANTIINFECTIVES FOR SYSTEMIC USE

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
UNII: W72I5ZT78Z
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)

MIA Detail

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]