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Moxalactam

Moxalactam structure

CAS No:
64952-97-2
Formula:
C20H20N6O9S
Chemical Name:
Moxalactam
Synonyms:
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)-;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-[6α,7α,7(R*)]]-;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)-;(6R,7R)-7-[[(2R)-2-Carboxy-2-(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;Moxalactam;Oxa-cephem;Latamoxef;Lamoxactam;Moxam;75007-71-5
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

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.

Solid

Moxalactam is 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. It has a role as an antibacterial drug. It is an oxacephem and a cephalosporin.|Latamoxef is a broad- spectrum beta-lactam antibiotic similar in structure to the cephalosporins except for the substitution of an oxaazabicyclo moiety for the thiaazabicyclo moiety of certain cephalosporins. It has been proposed especially for the meningitides because it passes the blood-brain barrier and for anaerobic infections.|Broad- spectrum beta-lactam antibiotic similar in structure to the CEPHALOSPORINS except for the substitution of an oxaazabicyclo moiety for the thiaazabicyclo moiety of certain CEPHALOSPORINS. It has been proposed especially for the meningitides because it passes the blood-brain barrier and for anaerobic infections.

Moxalactam Basic Attributes

Molecular Weight：

520.47

Exact Mass：

520.47

EC Number：

265-287-9

DSSTox ID：

DTXSID9023338

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

232

XLogP3：

-0.58

Density：

1.77 g/cm3

Melting Point：

117-122 °C

Boiling Point：

836ºC

Refractive Index：

1.768

Water Solubility：

7.51e-01 g/L

Storage Conditions：

2-8°C

Specific rotation：

D25 -15.3 ±2.6° (c = 0.216 in methanol)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

RN6824500

Toxicity

Toxicity Summary：

Latamoxef produces potentially life-threatening effects which include Bleeding, Hypothrombinemia, Platelet dysfunctioning. which are responsible for the discontinuation of Latamoxef therapy. The symptomatic adverse reactions produced by Latamoxef are more or less tolerable and if they become severe, they can be treated symptomatically, these include Diarrhea, Skin rashes, Hematuria, Hyperuricemia, Pyuria, Raised serum creatinine.

Protein Binding：

40%

Drug Information

Drug Indication：

Latamoxef is an oxacephem antibiotic usually grouped with the cephalosporins. It is used to treat bacterial infections. 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.

Pharmacology：

Latamoxef works by inhibiting bacterial cell wall biosynthesis.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Rapidly absorbed after oral administration.|Renal Excretion accounts for 75 %|8.51 L

Biological Half-Life：

1.6 hours

Mechanism of Action：

Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain (the penicillin-binding protein) by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that amoxicllin interferes with an autolysin inhibitor.

MeSH Entry Terms：

1 Oxacephalosporin

Moxalactam Use and Manufacturing

Uses

Anti-infective.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:520.5
XLogP3:-0.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:9
Exact Mass:520.10124741
Monoisotopic Mass:520.10124741
Topological Polar Surface Area:232
Heavy Atom Count:36
Complexity:958
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes