Latamoxef

Names

[ Name ]:
Latamoxef

[Synonym ]:
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
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
Latamoxef
lamoxactam
(R)-Moxalactam
5-oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-((carboxy(4-hydroxyphen
Listeria MOX Supplement,Moxalactam
Oxa-cephem
yl)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo
LMOX

Biological Activity

[Description]:

Moxalactam (Latamoxef) is a synthetic oxa-β-lactam antibiotic. Moxalactam has a broad spectrum of activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria. Moxalactam inhibits production of β-lactamases[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

β-lactamases[1]

[In Vitro]

Moxalactam (Latamoxef) inhibits 90% of strains of Escherichia coli, Klebsiella species, Proteus species, Morganella morganii, Neisseria gonorrhoeae, Neisseria meningitidis, Haemophilus influenzae and Salmonella species, including strains which are resistant to Cephalothin (HY-B1275A) and Gentamicin (HY-A0276A) at concentrations of less than 1 μg/mL[1]. Moxalactam exhibits moderate activity against P. aeruginosa and is usually active against other species of Pseudomonas, Acinetobacter species are usually resistant to Moxalactam[1]. Moxalactam has marked stability in vitro against a variety of β-lactamases, including that produced by B. fragilis, inhibits production of β-lactamases and does not induce class I β-lactamase[1].

[In Vivo]

Moxalactam (Latamoxef) (0-7.4 mg/mouse; s.c.; once) is effective against bacterial infections in mice[2]. Animal Model: Four-week-old male strain ICR mice, weighing 18-20 g, bacterial infection model[2] Dosage: 0-7.4 mg/mouse Administration: Subcutaneous injection, once Result: Showed protective activity with ED50s less than 7.4 mg/mouse against gram-positive and gram-negative bacterial infected mice.

[References]

[1]. Carmine AA, et al. Moxalactam (latamoxef). A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1983 Oct;26(4):279-333.

[2]. Goto S. In vitro and in vivo antibacterial activity of moxalactam, an oxa-β-lactam antibiotic. Clinical Infectious Diseases, 1982, 4(Supplement_3): S501-S510.

Chemical & Physical Properties

[ Density]:
1.77 g/cm3

[ Boiling Point ]:
836ºC

[ Melting Point ]:
117 - 122ºC

[ Molecular Formula ]:
C₂₀H₂₀N₆O₉S

[ Molecular Weight ]:
520.47300

[ Exact Mass ]:
520.10100

[ PSA ]:
231.60000

[ Index of Refraction ]:
1.768

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RN6824500

CHEMICAL NAME :: 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-

CAS REGISTRY NUMBER :: 64952-97-2

LAST UPDATED :: 199504

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C20-H20-N6-O9-S

MOLECULAR WEIGHT :: 520.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 480 mg/kg/4D-I

TOXIC EFFECTS :: Blood - hemorrhage

REFERENCE :: AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 99,126,1983 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5300 No. of Facilities: 69 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 5145 (estimated) No. of Female Employees: 4707 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RN6824500

Articles

A potential substrate binding conformation of β-lactams and insight into the broad spectrum of NDM-1 activity.

Antimicrob. Agents Chemother. 56(10) , 5157-63, (2012)

New Delhi metallo-β-lactamase 1 (NDM-1) is a key enzyme that the pathogen Klebsiella pneumonia uses to hydrolyze almost all β-lactam antibiotics. It is currently unclear why NDM-1 has a broad spectrum...

Comparison of cefoxitin and moxalactam 30 microg disc diffusion methods for detection of methicillin resistance in coagulase-negative staphylococci.

J. Antimicrob. Chemother. 59(4) , 763-6, (2007)

To compare cefoxitin and/or moxalactam 30 microg disc diffusion (DD) methods to detect methicillin resistance in coagulase-negative staphylococci (CoNS) using both high- and low-density (HD/LD) inocul...

Phosphate deprivation is associated with high resistance to latamoxef of gel-entrapped, sessile-like Escherichia coli cells.

J. Antimicrob. Chemother. 49(2) , 315-20, (2002)

Viable Escherichia coli cells were entrapped in agar gel layers and incubated in a phosphate-limited glucose medium. Immobilized bacteria displayed enhanced alkaline phosphatase activity and overexpre...

Related Compounds

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