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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 MOXALACTAM

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

Molecular Formula C20H20N6O9S
Molecular Weight 520.473
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Latamoxef

Cmax

ValueDoseCo-administeredAnalytePopulation
17.8 mg/L
500 mg single, intramuscular
LATAMOXEF plasma
Homo sapiens
21.8 mg/L
500 mg 3 times / day multiple, intramuscular
LATAMOXEF plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
294 μg × h/mL
1 g single, intravenous
LATAMOXEF serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.85 h
1 g single, intravenous
LATAMOXEF serum
Homo sapiens
0.23 h
500 mg single, intravenous
LATAMOXEF plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
1 g single, intravenous
LATAMOXEF serum
Homo sapiens

Doses

AEs

PubMed

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.
Substance Class Chemical
Record UNII
VUF6C936Z3
Record Status Validated (UNII)
Record Version