Moxalactam
Basic information
- CAS
64952-97-2- Standard SMILES
CO[C@@]1(NC(=O)C(C(=O)O)c2ccc(O)cc2)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CO[C@@H]21- InChIKey
JWCSIUVGFCSJCK-CAVRMKNVSA-N- Molecular formula
- C20H20N6O9S
- Average molar mass
- 520.5 g/mol
- Monoisotopic mass
- 520.10124741
Overview
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 a cephalosporin and an oxacephem.
Names & identifiers
- Preferred name
- Moxalactam
- IUPAC
- (6R,7R)-7-[[2-carboxy-2-(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- 7 beta-(2-carboxy-2-(4-hydroxyphenyl)acetamido)-7 alpha-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-1-oxa-1-dethia-3-cephem-4-carboxylic acid
- Molecular formula
- C20H20N6O9S
- Molecular weight
- 520.47
Names & synonyms
Latamoxefmoxalactam64952-97-2LamoxactamLatamoxefumOxa-cephemLMOXVUF6C936Z3(6R,7R)-7-[[2-carboxy-2-(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCHEBI:599928S-6059Disodium Moxalactam
Show more names
LatamoxefImpurity517 beta-(2-carboxy-2-(4-hydroxyphenyl)acetamido)-7 alpha-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-1-oxa-1-dethia-3-cephem-4-carboxylic acid5-Oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2S)-carboxy(4-hydroxyphenyl)acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)- (9CI)(6R-(6alpha,7alpha,7(S*)))-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 acid7-((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 (6R-(6alpha,7alpha,7(S*)))-
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 232 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 9
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 958
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
LogP-0.58
Solubility7.51e-01 g/L
Physical DescriptionSolid
Physicochemical properties
- Density
- 1.77 · 1.77±0.1 g/cm3(Predicted)
- pka
- 3.25 · 3.25±0.40(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - 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-[6.alpha.,7.alpha.,7(R*)]]-: Human health tier I assessment
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
latamoxef
DILI Negative
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding40%
PharmacodynamicsLatamoxef works by inhibiting bacterial cell wall biosynthesis.
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.
Biological Half-Life1.6 hours
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Rapidly absorbed after oral administration.
Renal Excretion accounts for 75 %
8.51 L
Cellular LocationsExtracellular
Additional notes
DefinitionChEBI: 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.
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