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Details

Stereochemistry EPIMERIC
Molecular Formula C20H20N6O9S
Molecular Weight 520.473
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LATAMOXEF

SMILES

CO[C@]2(NC(=O)C(C(O)=O)C1=CC=C(O)C=C1)[C@H]3OCC(CSC4=NN=NN4C)=C(N3C2=O)C(O)=O

InChI

InChIKey=JWCSIUVGFCSJCK-CAVRMKNVSA-N
InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1

HIDE SMILES / InChI

Description

Moxalactam (latamoxef) is a new synthetic oxa-beta-lactam antibiotic administered intravenously or intramuscularly. It has a broad spectrum of activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria, is particularly active against Enterobacteriaceae and is resistant to hydrolysis by beta-lactamases. Moxalactam has moderate activity against Pseudomonas aeruginosa, but on the basis of present evidence can not be recommended as sole antibiotic treatment of known or suspected pseudomonal infections. Like the related compounds, the cephalosporins, moxalactam is effective in the treatment of complicated urinary tract infections and lower respiratory tract infections caused by Gram-negative bacilli. Latamoxef works by inhibiting bacterial cell wall biosynthesis. Latamoxef is primarily indicated in conditions like Bone and joint infection, GI infections, Gynecological infections, Meningitis, Respiratory tract infections, Septicaemia, Skin infections, Soft tissue infections, UTI. Latamoxef is no longer available in the United States.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
Latamoxef
PMID

PMID

TitleDatePMID
The comparative beta-lactamase resistance and inhibitory activity of 1-oxa cephalosporin, cefoxitin and cefotaxime.
1979 Sep
Comparative in vitro activity and beta-lactamase stability of moxalactam and other selected cephalosporin antibiotics.
1981
In vitro susceptibility of Mycobacterium fortuitum to N-formimidoyl thienamycin and several cephamycins.
1982 Dec
Evaluation of lamoxactam in the treatment of severe bacterial infections.
1983
A single injection of moxalactam for acute gonorrhea.
1983
Third-generation cephalosporins for polymicrobial surgical sepsis.
1983 Feb
Prolonged bleeding times and bleeding diathesis associated with moxalactam administration.
1983 Jan 7
Enterococcal liver abscess associated with moxalactam therapy. Review of literature on enterococcal superinfections in association with moxalactam therapy.
1983 Sep
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.
1985 Jan
Moxalactam myoclonus, seizures, and encephalopathy.
1986 Mar
A double beta-lactam combination versus an aminoglycoside-containing regimen as empiric antibiotic therapy for febrile granulocytopenic cancer patients.
1986 May 30
Studies on the nephrotoxicity of aminoglycoside antibiotics and protection from these effects (3). Protective effect of latamoxef against tobramycin nephrotoxicity and its protective mechanism.
1986 Nov
Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients.
1986 Nov
In vitro susceptibility of Mycobacterium avium complex to antibacterial agents.
1987 Nov
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.
1987 Oct
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.
1988 Dec
[A case of hematuria associated with cefem group antibiotics].
1992 Feb
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.
1996 Jul-Aug
Patent

Sample Use Guides

In Vivo Use Guide
Intramuscular Susceptible infections Adult: 2 g/day in 2 divided doses. Child: 50-100 mg/kg/day in 2-3 divided doses. Intravenous Susceptible infections Adult: 2-6 g/day in 2-3 divided doses. Child: 50-100 mg/kg/day in 2-3 divided doses. Intravenous Meningitis Child: 100 mg/kg as loading dose.
Route of Administration: Parenteral
In Vitro Use Guide
Moxalactam (latamoxef) showed great antibacterial activity to Enterobacteriaceae spp., including ESBLs-producing Escherichia coli, Klebsiella pneumoniae, and Proteus spp., with the MIC(50), MIC(90), and susceptibility rates of 0.25-4 mg/L, 0.5-8 mg/L, and >90%, respectively.
Name Type Language
LATAMOXEF
INN   WHO-DD  
INN  
Official Name English
5-OXA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((CARBOXY(4-HYDROXYPHENYL)ACETYL)AMINO)-7-METHOXY-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, (6R,7R)-
Common Name English
MOXALACTAM
MI   VANDF  
Common Name English
MOXALACTAM [VANDF]
Common Name English
LATAMOXEF [JAN]
Common Name English
MOXALACTAM [MI]
Common Name English
(6R,7R)-7-((CARBOXY(4-HYDROXYPHENYL)ACETYL)AMINO)-7-METHOXY-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-5-OXA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
LATAMOXEF [WHO-DD]
Common Name English
LATAMOXEF [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01DD06
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
WHO-ATC J01DD06
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
Code System Code Type Description
EVMPD
SUB08408MIG
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
DRUG BANK
DB04570
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
ECHA (EC/EINECS)
265-287-9
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
WIKIPEDIA
LATAMOXEF
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
CAS
64952-97-2
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
NCI_THESAURUS
C670
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
INN
4880
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
RXCUI
7069
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY RxNorm
MERCK INDEX
M7642
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL74632
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
MESH
D009070
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY
PUBCHEM
47499
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY SWITZERF
EPA CompTox
64952-97-2
Created by admin on Tue Mar 06 12:17:13 UTC 2018 , Edited by admin on Tue Mar 06 12:17:13 UTC 2018
PRIMARY