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Latamoxef

Latamoxef Structure
CAS No.
64952-97-2
Chemical Name:
Latamoxef
Synonyms
LMOX;C07231;latamoxef;Oxa-cephem;lamoxactam;Latamoxef Acid;Latamoxef USP/EP/BP;Listeria MOX Supplement, Moxalactam;4-Isoxazolecarboxylicacid,5-hydroxy-8-methyl-,ethylester;5-oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-((carboxy(4-hydroxyphen
CBNumber:
CB7497197
Molecular Formula:
C20H20N6O9S
Molecular Weight:
520.47
MOL File:
64952-97-2.mol
Modify Date:
2022/12/21 16:56:50

Latamoxef Properties

Melting point 117-122° (dec)
alpha D25 -15.3 ±2.6° (c = 0.216 in methanol)
Density 1.77±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,2-8°C
pka 3.25±0.40(Predicted)

SAFETY

Risk and Safety Statements

WGK Germany  3
RTECS  RN6824500

Latamoxef Chemical Properties,Uses,Production

Uses

Latamoxef is an oxacephem antibiotic usually grouped with the cephalosporins. An anti-bacterial agent.

Definition

ChEBI: A broad-spectrum oxacephem antibiotic in which the oxazine ring is substituted with a tetrazolylthiomethyl group and the azetidinone ring carries methoxy and 2-carboxy-2-(4-hydroxyphenyl)acetamido substituents.

World Health Organization (WHO)

Latamoxef, a cefamycin antibiotic, was introduced in 1982 for the treatment of serious infections. Its use has subsequently been associated with reports of clinically important haemorrhage, sometimes fatal, and in some countries routine co-administration of vitamin K is advised to minimize this risk.

Antimicrobial activity

Moxalactam. A semisynthetic 7-methoxyoxacephem, supplied as the disodium salt.It is generally slightly less active than cefotaxime, especially against Staph. aureus, but unlike other group 4 cephalosporins it exhibits fairly good activity against B. fragilis. Other Bacteroides spp. are generally less susceptible. The 7-methoxy substitution, also found in cephamycins such as cefoxitin, confers resistance to hydrolysis by a wide range of β-lactamases including those of Staph. aureus, various enterobacteria and B. fragilis. Resistance, predominantly in Enterobacter spp., Ps. aeruginosa and Ser. marcescens due to induction of chromosomal enzymes, has been found in vitro and in some patients.
A 500 mg intramuscular injection achieves a serum concentration of 12–22 mg/L after 1.2 h. Infusion of 1 g over 30 min results in a concentration of 60 mg/L. The plasma half-life is c. 2 h and plasma protein binding 40–50%. There is reasonably good penetration into serous fluids, the concentration in ascitic fluid reaching 75% and in pleural fluid 50% of the concentration simultaneously present in the serum. Levels of 5–35 mg/L have been obtained in inflamed meninges. Sputum levels are of the order of 2 mg/L following 1 g of the drug intravenously.
Renal elimination accounts for 90% of the clearance, but significant concentrations are found in the feces. Excretion is depressed in renal failure. Hemodialysis removes 48–51% of the drug in 4 h; peritoneal dialysis has little or no effect.
Increased bleeding and decreases in platelet function associated with the methylthiotetrazole side chain are sufficiently common to have been cited as reasons for restricting use of the agent. Use is contraindicated in patients on anticoagulant therapy. Uses are similar to those of group 4 cephalosporins. It is generally less successful in the treatment of infections due to Gram-positive organisms.

Latamoxef Preparation Products And Raw materials

Raw materials

Preparation Products

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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- 5-Oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-carboxy-2-(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)- LMOX C07231 5-oxa-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-((carboxy(4-hydroxyphen lamoxactam latamoxef Latamoxef 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 5-Oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-carboxy(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)- (9CI) 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-[6a,7a,7(R*)]]- Oxa-cephem 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 Listeria MOX Supplement, Moxalactam yl)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo- Latamoxef USP/EP/BP Latamoxef Acid 4-Isoxazolecarboxylicacid,5-hydroxy-8-methyl-,ethylester 64952-97-2