MOXALACTAM

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6354685 | https://www.ncbi.nlm.nih.gov/pubmed/6210519

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 Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3918982 \| https://www.drugbank.ca/drugs/DB04570 \| https://www.ncbi.nlm.nih.gov/pubmed/2327782 \| https://www.ncbi.nlm.nih.gov/pubmed/6448573	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: http://www.mims.com/singapore/drug/info/latamoxef?mtype=generic https://www.ncbi.nlm.nih.gov/pubmed/6210519	Curative		Approved 8429	Latamoxef Approved Use Susceptible infections.

C_max

Value	Dose	Co-administered	Analyte	Population
17.8 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6643333	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6643333	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

Value	Dose	Co-administered	Analyte	Population
294 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6252833	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6643333	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6252833	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6252833	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/6479022	unhealthy, 7 days - 34 years n = 40 Health Status: unhealthy Age Group: 7 days - 34 years Sex: M+F Population Size: 40 Sources: https://pubmed.ncbi.nlm.nih.gov/6479022	Disc. AE: Neutropenia... AEs leading to discontinuation/dose reduction: Neutropenia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6479022
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: https://pubmed.ncbi.nlm.nih.gov/6456688	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: https://pubmed.ncbi.nlm.nih.gov/6456688	Disc. AE: Fever... AEs leading to discontinuation/dose reduction: Fever (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6456688

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/6479022	unhealthy, 7 days - 34 years n = 40 Health Status: unhealthy Age Group: 7 days - 34 years Sex: M+F Population Size: 40 Sources: https://pubmed.ncbi.nlm.nih.gov/6479022
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: https://pubmed.ncbi.nlm.nih.gov/6456688	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: https://pubmed.ncbi.nlm.nih.gov/6456688

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1274	http://www.3bsc.com/index/pro_info.php?id=54990
AHH Chemical co.,ltd	MT-53236	http://www.ahhchemical.com/product/MT-53236.html
AK Scientific, Inc. (AKSCI)	7002AB	http://www.aksci.com/item_detail.php?cat=7002AB
Aurora Fine Chemicals LLC	A13.111.321	http://online.aurorafinechemicals.com/info?ID=A13.111.321
AvaChem Scientific	2856	http://www.avachem.com/productSearch.asp?2856
BLD Pharm	BD140444	http://www.bldpharm.com/products/64952-97-2.html
BioChemPartner	BCP12584	http://www.biochempartner.com/64952-97-2-BCP12584
ChemMol	49424120	http://www.chemmol.com/chemmol/49424120.html
ChemMol	99124802	http://www.chemmol.com/chemmol/99124802.html
OChem	20327	http://www.ocheminc.com/index.php?act=psearch&pid=649L972
Sigma-Aldrich	43963_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/43963?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S532543	http://www.smolecule.com/products/s532543
THE BioTek	bt-272602	https://www.thebiotek.com/product/inhibitors/bt-272602
THE BioTek	bt-312006	https://www.thebiotek.com/product/others/bt-312006
eNovation Chemicals	D674447	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674447

PubMed

Title	Date	PubMed
The comparative beta-lactamase resistance and inhibitory activity of 1-oxa cephalosporin, cefoxitin and cefotaxime.	1979 Sep	315938
Comparative in vitro activity and beta-lactamase stability of moxalactam and other selected cephalosporin antibiotics.	1981	6457607
In vitro susceptibility of Mycobacterium fortuitum to N-formimidoyl thienamycin and several cephamycins.	1982 Dec	6961887
Evaluation of lamoxactam in the treatment of severe bacterial infections.	1983	6617297
A single injection of moxalactam for acute gonorrhea.	1983	6616526
Third-generation cephalosporins for polymicrobial surgical sepsis.	1983 Feb	6295339
Prolonged bleeding times and bleeding diathesis associated with moxalactam administration.	1983 Jan 7	6217353
Enterococcal liver abscess associated with moxalactam therapy. Review of literature on enterococcal superinfections in association with moxalactam therapy.	1983 Sep	6225403
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.	1985 Jan	3920957
Moxalactam myoclonus, seizures, and encephalopathy.	1986 Mar	3956381
A double beta-lactam combination versus an aminoglycoside-containing regimen as empiric antibiotic therapy for febrile granulocytopenic cancer patients.	1986 May 30	3521269
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	3820859
Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients.	1986 Nov	3778044
In vitro susceptibility of Mycobacterium avium complex to antibacterial agents.	1987 Nov	3440370
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.	1987 Oct	3501698
In-vitro activity of seventeen antimicrobial compounds against seven species of mycobacteria.	1988 Dec	3243734
[A case of hematuria associated with cefem group antibiotics].	1992 Feb	1561959
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996 Jul-Aug	9131470

Patents

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

MOXALACTAM

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

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