LORACARBEF

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H16ClN3O4.H2O
Molecular Weight	367.784
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.N[C@@H](C(=O)N[C@H]1[C@H]2CCC(Cl)=C(N2C1=O)C(O)=O)C3=CC=CC=C3

InChI

InChIKey=GPYKKBAAPVOCIW-HSASPSRMSA-N

InChI=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

HIDE SMILES / InChI

Molecular Formula	C16H16ClN3O4
Molecular Weight	349.769
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2621166
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7686466 | http://www.rxlist.com/lorabid-drug.htm

Loracarbef (KT3777) is carbacephem antibiotic structurally identical to cefaclor, except that the sulfur atom of position 1 of the cephem nucleus has been replaced by carbon. It showed good affinity for penicillin-binding proteins. At low concentrations (< 2 mg/L) in vitro, it inhibits Streptococcus pneumoniae, S. pyogenes, beta-haemolytic streptococci groups B, C and G. Proteus mirabilis and Moraxella catarrhalis, including beta-lactamase-producing strains. At therapeutic plasma concentrations it is also active in vitro against most strains of Staphylococcus aureus, S. saprophyticus, Escherichia coli and beta-lactamase-positive and -negative strains of Haemophilus influenzae. Loracarbef has been indicated in the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2621166	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7686466	Curative		Approved 8583	LORABID Approved Use Loracarbef is indicated in the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the conditions listed below. (As recommended dosages, durations of therapy, and applicable patient populations vary among these infections, please see DOSAGE AND ADMINISTRATION for specific recommendations.) Lower Respiratory Tract: Secondary Bacterial Infection of Acute Bronchitis caused by S. pneumoniae, H. influenzae(including b-lactamase-producing strains), or M. catarrhalis (including b-lactamase-producing strains). Acute Bacterial Exacerbations of Chronic Bronchitis: caused by S. pneumoniae, H. influenzae (including b-lactamase-producing strains), or M. catarrhalis (including b-lactamase-producing strains). Pneumonia: caused by S. pneumoniae or H. influenzae (non-b-lactamase-producing strains only). Data are insufficient at this time to establish efficacy in patients with pneumonia caused by b-lactamase-producing strains of H. influenzae. Upper Respiratory Tract: Otitis Media† caused by S. pneumoniae, H. influenzae (including b-lactamase-producing strains), M. catarrhalis (including b-lactamase-producing strains), or S. pyogenes. Acute Maxillary Sinusitis:† caused by S. pneumoniae, H. influenzae (non-b-lactamase-producing strains only), or M. catarrhalis (including b-lactamase-producing strains). Data are insufficient at this time to establish efficacy in patients with acute maxillary sinusitis caused by b-lactamase-producing strains of H. influenzae. † NOTE: In a patient population with significant numbers of b-lactamase-producing organisms, loracarbef's clinical cure and bacteriological eradication rates were somewhat less than those observed with a product containing a b-lactamase inhibitor. Loracarbef's decreased potential for toxicity compared to products containing b-lactamase inhibitors along with the susceptibility patterns of the common microbes in a given geographic area should be taken into account when considering the use of an antimicrobial (see CLINICAL STUDIES.) Pharyngitis and Tonsillitis: caused by S. pyogenes. (The usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever, is penicillin administered by the intramuscular route. Loracarbef is generally effective in the eradication of S. pyogenes from the nasopharynx; however, data establishing the efficacy of loracarbef in the subsequent prevention of rheumatic fever are not available at present.) For information on use in pediatric patients, see PRECAUTIONS, Pediatric Use. Skin and Skin Structure: Uncomplicated Skin and Skin Structure Infections caused by S. aureus (including penicillinase-producing strains) or S. pyogenes. Abscesses should be surgically drained as clinically indicated. Urinary Tract: Uncomplicated Urinary Tract Infections (cystitis) caused by E. coli or S. saprophyticus. NOTE: In considering the use of loracarbef in the treatment of cystitis, loracarbef's lower bacterial eradication rates and lower potential for toxicity should be weighed against the increased eradication rates and increased potential for toxicity demonstrated by some other classes of approved agents (see CLINICAL STUDIES.) Uncomplicated Pyelonephritis: caused by E. coli. Although treatment of infections due to this organism in this organ system demonstrated a clinically acceptable overall outcome, efficacy was studied in fewer than 10 infections. Culture and susceptibility testing should be performed when appropriate to determine the causative organism and its susceptibility to loracarbef. Therapy may be started while awaiting the results of these studies. Once these results become available, antimicrobial therapy should be adjusted accordingly. Launch Date 1991

C_max

Value	Dose	Analyte	Population
19.21 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1468429	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LORACARBEF serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
13.64 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1468429	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LORACARBEF serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050667ap.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LORACARBEF plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
14 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050667ap.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LORACARBEF plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
33.04 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1468429	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LORACARBEF serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
35.38 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1468429	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LORACARBEF serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
70.31 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1468429	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LORACARBEF serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
102.33 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1468429	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LORACARBEF serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/	Disc. AE: Diarrhea, Allergic exanthema... AEs leading to discontinuation/dose reduction: Diarrhea (1 patient) Allergic exanthema (1 patient) Abdominal pain (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/
30 mg/kg 1 times / day steady, oral Highest studied dose Dose: 30 mg/kg, 1 times / day Route: oral Route: steady Dose: 30 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	unhealthy, children and adults Health Status: unhealthy Age Group: children and adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	Disc. AE: Hypersensitivity, Diarrhea... AEs leading to discontinuation/dose reduction: Hypersensitivity (16 patients) Diarrhea (12 patients) Nausea and vomiting (16 patients) Abdominal pain (9 patients) Headache (5 patients) Neurologic disorder NOS (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/

AEs

AE	Significance	Dose	Population
Abdominal pain	1 patient Disc. AE	400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/
Allergic exanthema	1 patient Disc. AE	400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/
Diarrhea	1 patient Disc. AE	400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1621747/
Diarrhea	12 patients Disc. AE	30 mg/kg 1 times / day steady, oral Highest studied dose Dose: 30 mg/kg, 1 times / day Route: oral Route: steady Dose: 30 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	unhealthy, children and adults Health Status: unhealthy Age Group: children and adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/
Hypersensitivity	16 patients Disc. AE	30 mg/kg 1 times / day steady, oral Highest studied dose Dose: 30 mg/kg, 1 times / day Route: oral Route: steady Dose: 30 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	unhealthy, children and adults Health Status: unhealthy Age Group: children and adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/
Nausea and vomiting	16 patients Disc. AE	30 mg/kg 1 times / day steady, oral Highest studied dose Dose: 30 mg/kg, 1 times / day Route: oral Route: steady Dose: 30 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	unhealthy, children and adults Health Status: unhealthy Age Group: children and adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/
Neurologic disorder NOS	2 patients Disc. AE	30 mg/kg 1 times / day steady, oral Highest studied dose Dose: 30 mg/kg, 1 times / day Route: oral Route: steady Dose: 30 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	unhealthy, children and adults Health Status: unhealthy Age Group: children and adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/
Headache	5 patients Disc. AE	30 mg/kg 1 times / day steady, oral Highest studied dose Dose: 30 mg/kg, 1 times / day Route: oral Route: steady Dose: 30 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	unhealthy, children and adults Health Status: unhealthy Age Group: children and adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/
Abdominal pain	9 patients Disc. AE	30 mg/kg 1 times / day steady, oral Highest studied dose Dose: 30 mg/kg, 1 times / day Route: oral Route: steady Dose: 30 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/	unhealthy, children and adults Health Status: unhealthy Age Group: children and adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1621742/

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1NR4Q4
AmicBase - Antimicrobial Activities	2165
BOC Sciences	121961-22-6
BOC Sciences	76470-66-1
Chem Scene	CS-0013651	http://www.chemscene.com/76470-66-1.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0820439
ChemTik	CTK2H7568
Compound Cloud	5284584
Compound Cloud	5284585
eMolecules	36552993
eMolecules	42853740
eNovation Chemicals	D674508	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674508
eNovation Chemicals	Y1077622	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1077622
Glentham Life Sciences	GP0853	http://www.glentham.com/products/product/GP0853/
MedChem Express	HY-B1682	https://www.medchemexpress.com/loracarbef.html
MuseChem	R053832	https://www.musechem.com/product/R053832.html
Smolecule	S533550	http://www.smolecule.com/products/s533550
THE BioTek	bt-273707	https://www.thebiotek.com/product/inhibitors/bt-273707
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-5897A
ZINC	ZINC000001530993	http://zinc15.docking.org/substances/ZINC000001530993

PubMed

Title	Date	PubMed
Progress in the development of early diagnosis and a drug with unique pharmacology to improve cancer therapy.	2008-10-13	18644768
The effect of four different types of diet on the bioavailability of loracarbef.	2008-03-20	18348469
Antimicrobial susceptibility of Staphylococcus aureus isolated from colonized hospital personnel.	2007-06-19	17571573
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Twice-daily dosing of loracarbef 15 mg/kg versus 30 mg/kg in the treatment of children with acute sinusitis.	2005	16444905
[Evaluation of predisposing factors and bacteriologic agents in pediatric rhinosinusitis].	2005	16340293
Penicillin V, loracarbef and clindamycin in tonsillar surface fluid during acute group A streptococcal pharyngotonsillitis.	2005	16012002
Staphylococcal skin infections in children: rational drug therapy recommendations.	2005	15871629
Limited spread of penicillin-nonsusceptible pneumococci, Skåne County, Sweden.	2004-06	15207061
Antibiotic selection pressure and resistance in Streptococcus pneumoniae and Streptococcus pyogenes.	2004-03	15109426
Antimicrobial susceptibility patterns, beta-lactamases, and biochemical identification of Yokenella regensburgei strains.	2004-01	14761716
Cefdinir: a review of its use in the management of mild-to-moderate bacterial infections.	2004	15212560
Natural antibiotic susceptibility of Ewingella americana strains.	2003-10	14598935
Natural antibiotic susceptibility of strains of Serratia marcescens and the S. liquefaciens complex: S. liquefaciens sensu stricto, S. proteamaculans and S. grimesii.	2003-07	12842326
[Haemophilus influenzae and betalactam resistance: description of bla TEM gene deletion].	2003-06	12973457
Serologically documented loracarbef (Lorabid)-induced immune thrombocytopenia.	2003-05	12701119
Natural antimicrobial susceptibilities of strains of 'unusual' Serratia species: S. ficaria, S. fonticola, S. odorifera, S. plymuthica and S. rubidaea.	2003-04	12654765
[Sensitivity of Haemophilus influenzae isolates in Spain to 17 oral antibiotics].	2003-03	12586017
Natural antibiotic susceptibility of Proteus spp., with special reference to P. mirabilis and P. penneri strains.	2003-02	12678409
Contribution of efflux to cefuroxime resistance in clinical isolates of Escherichia coli.	2003	14514145
Natural antibiotic susceptibility of Enterobacter amnigenus, Enterobacter cancerogenus, Enterobacter gergoviae and Enterobacter sakazakii strains.	2002-09	12427217
The fecal microflora of 1-3-month-old infants during treatment with eight oral antibiotics.	2002-06	12120942
Patient, physician, and nurse satisfaction with antibiotics.	2002-06	12086194
Antimicrobial susceptibilities of clinical isolates of Haemophilus influenzae and Moraxella catarrhalis collected during 1999-2000 from 13 countries.	2001-12	11843908
Structures of ceftazidime and its transition-state analogue in complex with AmpC beta-lactamase: implications for resistance mutations and inhibitor design.	2001-08-07	11478888
Effect of step-down therapy of ceftriaxone plus loracarbef versus parenteral therapy of ceftriaxone on the intestinal microflora in patients with community-acquired pneumonia.	2001-07	11531985
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.	2001-01	11245326
Compliance issues related to the selection of antibiotic suspensions for children.	2001-01	11176558
Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells.	1994-04-20	8155686
Loracarbef. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy.	1993-05	7686466
Loracarbef: a new orally administered carbacephem antibiotic.	1993-03	8453172
Loracarbef (LY163892) versus cefaclor and norfloxacin in the treatment of uncomplicated pyelonephritis.	1992-06-22	1621752
Loracarbef (LY163892) versus cefaclor in the treatment of bacterial skin and skin-structure infections in an adult population.	1992-06-22	1621751
Loracarbef versus penicillin VK in the treatment of streptococcal pharyngitis and tonsillitis in an adult population.	1992-06-22	1621750
The carbacephems: a new beta-lactam antibiotic class.	1992-06-22	1621741

Patents

Sample Use Guides

In Vivo Use Guide

In the treatment of adults with pharyngitis, acute bronchitis, tonsillitis and uncomplicated infections of skin and skin structures, loracarbef was studied at a dosage of 200mg twice daily. Patients with acute pneumonia, sinusitis and uncomplicated pyelonephritis were treated with 400mg twice daily in clinical studies. Seven-day courses of 200 or 400mg twice daily were used to treat acute exacerbations of chronic bronchitis (acute superimposed on chronic). A once-daily dose of 200mg is used to treat acute cystitis. In infants and children, 30 mg/kg in divided doses 12-hourly is used to treat acute otitis media, while 15 mg/kg is recommended for the treatment of pharyngitis, tonsillitis and impetigo. Dosage should be adjusted in patients with renal impairment whose creatine clearance is below 2.9 L/h (49 ml/min).

Route of Administration: Oral

In Vitro Use Guide

The MIC50 of loracarbef (KT3777) ranged from 0.2 to 3.13 micrograms/ml for clinical isolates of Staphylococcus aureus, Streptococci, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Haemophilus influenzae, and Neisseria gonorrhoeae.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:59:49 GMT 2025` Edited by `admin` on `Mon Mar 31 17:59:49 GMT 2025`
Record UNII	3X11EVM5SU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LORACARBEF

Official Name

English

LORACARBEF MONOHYDRATE

Preferred Name

English

LORACARBEF [USAN]

Common Name

English

LORABID

Brand Name

English

LY163892 MONOHYDRATE

Code

English

(6R,7S)-7-[(R)-2-Amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, monohydrate

Common Name

English

LY-163892 MONOHYDRATE

Code

English

1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINOPHENYLACETYL)AMINO)-3-CHLORO-8-OXO-, MONOHYDRATE, (6R-(6.ALPHA.,7.BETA.(R*)))-

Common Name

English

LORACARBEF [VANDF]

Common Name

English

LORACARBEF [JAN]

Common Name

English

LORACARBEF [USP IMPURITY]

Common Name

English

LORACARBEF [ORANGE BOOK]

Common Name

English

LORACARBEF MONOHYDRATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357