| Common Name |
Latamoxef
| Description |
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. [PubChem]
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
FestamoxinChEBI
LamoxactamChEBI
LatamoxefumChEBI
LMOXChEBI
Oxa-cephemChEBI
MoxalactamHMDB
Disodium latamoxefMeSH
Disodium, moxalactamMeSH
Latamoxef, disodiumMeSH
1 OxacephalosporinMeSH
1-OxacephalosporinMeSH
Disodium moxalactamMeSH
Moxalactam disodiumMeSH
Moxalactam, disodiumMeSH
ShiomarinMeSH
| Chemical Formlia |
C20H20N6O9S
| Average Molecliar Weight |
520.473
| Monoisotopic Molecliar Weight |
520.101246958
| IUPAC Name |
(6R,7R)-7-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)slifanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
| Traditional Name |
latamoxef
| CAS Registry Number |
64952-97-2
| SMILES |
[H][C@]12OCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)C(C(O)=O)C1=CC=C(O)C=C1)OC)C(O)=O
| InChI Identifier |
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
| InChI Key |
JWCSIUVGFCSJCK-CAVRMKNVSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
| Kingdom |
Organic compounds
| Super Class |
Organic acids and derivatives
| Class |
Carboxylic acids and derivatives
| Sub Class |
Amino acids, peptides, and analogues
| Direct Parent |
N-acyl-alpha amino acids and derivatives
| Alternative Parents |
Phenylacetamides
Oxacephems
1-hydroxy-2-unsubstituted benzenoids
Alkylarylthioethers
1,3-dicarbonyl compounds
Dicarboxylic acids and derivatives
Tetrazoles
Tertiary carboxylic acid amides
Heteroaromatic compounds
Secondary carboxylic acid amides
Azetidines
Slifenyl compounds
Oxacyclic compounds
Azacyclic compounds
Carboxylic acids
Organonitrogen compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
N-acyl-alpha amino acid or derivatives
Phenylacetamide
Oxacephem
Aryl thioether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkylarylthioether
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
1,3-dicarbonyl compound
Azole
Beta-lactam
Heteroaromatic compound
Tertiary carboxylic acid amide
Tetrazole
Azetidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Slifenyl compound
Thioether
Organoslifur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
cephalosporin (CHEBI:599928 )
oxacephem (CHEBI:599928 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Bacterial Agents
Cephalosporins
| Application |
Pharmaceutical
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.51e-01 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.75 mg/mLALOGPS
logP0.22ALOGPS
logP0.17ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area206.3 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.7 m3·mol-1ChemAxon
Polarizability47.24 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04570
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04570
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB04570
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
43215
| KEGG Compound ID |
C07231
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Latamoxef
| NuGOwiki Link |
HMDB15574
| Metagene Link |
HMDB15574
| METLIN ID |
Not Available
| PubChem Compound |
47499
| PDB ID |
Not Available
| ChEBI ID |
599928
Product: Flumequine
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M: Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients. Arch Intern Med. 1986 Nov;146(11):2159-64. [PubMed:3778044 ]
- Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71. [PubMed:6217353 ]
|
PMID: 26824411
