Latamoxef (CHEM022336)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:28:40 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022336
Identification
Common NameLatamoxef
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
FestamoxinChEBI
LamoxactamChEBI
LatamoxefumChEBI
LMOXChEBI
Oxa-cephemChEBI
MoxalactamHMDB
Disodium latamoxefHMDB
Disodium, moxalactamHMDB
Latamoxef, disodiumHMDB
1 OxacephalosporinHMDB
1-OxacephalosporinHMDB
Disodium moxalactamHMDB
Moxalactam disodiumHMDB
Moxalactam, disodiumHMDB
ShiomarinHMDB
LatamoxefChEBI
Chemical FormulaC20H20N6O9S
Average Molecular Mass520.473 g/mol
Monoisotopic Mass520.101 g/mol
CAS Registry Number64952-97-2
IUPAC Name(6R,7R)-7-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namelatamoxef
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 IdentifierInChI=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 KeyJWCSIUVGFCSJCK-CAVRMKNVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
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
  • Sulfenyl compound
  • Thioether
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.7 m³·mol⁻¹ChemAxon
Polarizability47.24 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufu-2554920000-9ccc16f5a0c811c8cb66Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-5002069000-fcfc4810dc087dc9855aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fml-0110950000-57d22894c62264be15e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0930200000-7e6509b24b50b053a363Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0920100000-299f3fd6d8a2eefd712dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1967610000-776d7de6814af49746f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-8910400000-1fe14d5c919b1042fa01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-5970000000-1f1d3cbaec8e0aab9848Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0302290000-5de96a5b13c0e07919d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0836490000-991b57dd6b18e8d73d35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1901300000-73b3b88db9aeadfe3609Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0701390000-e8d5e3d3c75f5a8a82dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2910020000-c32579f60fb91a6747f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-6911000000-20efb6f673da8484a976Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04570
HMDB IDHMDB0015574
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLatamoxef
Chemspider ID43215
ChEBI ID599928
PubChem Compound ID47499
Kegg Compound IDC07231
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24956910
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3296254
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3477883
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3778044
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=4222777
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=6129432
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6217353
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9131470
10. 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.
11. Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71.