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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

[H][C@]12OCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)C(C(O)=O)C4=CC=C(O)C=C4)OC)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
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
17.8 mg/L
500 mg single, intramuscular
dose: 500 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
LATAMOXEF plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
21.8 mg/L
500 mg 3 times / day multiple, intramuscular
dose: 500 mg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
LATAMOXEF plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
294 μg × h/mL
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LATAMOXEF serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.23 h
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LATAMOXEF plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.85 h
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LATAMOXEF serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
1 g single, intravenous
dose: 1 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LATAMOXEF serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
50 mg/kg 3 times / day multiple, intravenous
Dose: 50 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 50 mg/kg, 3 times / day
Sources:
unhealthy, 7 days - 34 years
n = 40
Health Status: unhealthy
Age Group: 7 days - 34 years
Sex: M+F
Population Size: 40
Sources:
Disc. AE: Neutropenia...
AEs leading to
discontinuation/dose reduction:
Neutropenia (2 patients)
Sources:
50 mg/kg 1 times / day multiple, intravenous (mean)
Dose: 50 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, 8 days - 98 years
n = 50
Health Status: unhealthy
Condition: nfectious disorders
Age Group: 8 days - 98 years
Sex: M+F
Population Size: 50
Sources:
Disc. AE: Fever...
AEs leading to
discontinuation/dose reduction:
Fever (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Neutropenia 2 patients
Disc. AE
50 mg/kg 3 times / day multiple, intravenous
Dose: 50 mg/kg, 3 times / day
Route: intravenous
Route: multiple
Dose: 50 mg/kg, 3 times / day
Sources:
unhealthy, 7 days - 34 years
n = 40
Health Status: unhealthy
Age Group: 7 days - 34 years
Sex: M+F
Population Size: 40
Sources:
Fever 1 patient
Disc. AE
50 mg/kg 1 times / day multiple, intravenous (mean)
Dose: 50 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, 8 days - 98 years
n = 50
Health Status: unhealthy
Condition: nfectious disorders
Age Group: 8 days - 98 years
Sex: M+F
Population Size: 50
Sources:
PubMed

PubMed

TitleDatePubMed
In vitro susceptibility of Mycobacterium fortuitum to N-formimidoyl thienamycin and several cephamycins.
1982 Dec
Third-generation cephalosporins for polymicrobial surgical sepsis.
1983 Feb
Prolonged bleeding times and bleeding diathesis associated with moxalactam administration.
1983 Jan 7
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.
1985 Jan
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
[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
Patents

Sample Use Guides

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
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
Created
by admin
on Sat Dec 16 16:54:42 UTC 2023
Edited
by admin
on Sat Dec 16 16:54:42 UTC 2023
Record UNII
VUF6C936Z3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOXALACTAM
MI   VANDF  
Common 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
LATAMOXEF
INN   WHO-DD  
INN  
Official Name English
MOXALACTAM [VANDF]
Common Name English
LATAMOXEF [JAN]
Common Name English
Latamoxef [WHO-DD]
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 [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01DD06
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
NCI_THESAURUS C357
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
WHO-ATC J01DD06
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
Code System Code Type Description
DRUG CENTRAL
1851
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
EVMPD
SUB08408MIG
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
DRUG BANK
DB04570
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
CHEBI
599928
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
265-287-9
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
WIKIPEDIA
LATAMOXEF
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
CAS
64952-97-2
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
NCI_THESAURUS
C670
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
INN
4880
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
RXCUI
7069
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY RxNorm
SMS_ID
100000082578
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
FDA UNII
VUF6C936Z3
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
MERCK INDEX
m7642
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL74632
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
MESH
D009070
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
PUBCHEM
47499
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023338
Created by admin on Sat Dec 16 16:54:42 UTC 2023 , Edited by admin on Sat Dec 16 16:54:42 UTC 2023
PRIMARY
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