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Identification
NameLatamoxef
Accession NumberDB04570
TypeSmall Molecule
GroupsApproved
DescriptionBroad- 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
Thumb
Synonyms
Lamoxactam
Latamoxef
Latamoxefum
LMOX
moxalactam
Oxa-cephem
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Latamoxef disodium
64953-12-4
Thumb
  • InChI Key: GRIXGZQULWMCLU-HUTAOCTPSA-L
  • Monoisotopic Mass: 564.06513592
  • Average Mass: 564.44
DBSALT001335
Categories
UNIIVUF6C936Z3
CAS number64952-97-2
WeightAverage: 520.473
Monoisotopic: 520.101246958
Chemical FormulaC20H20N6O9S
InChI KeyJWCSIUVGFCSJCK-CAVRMKNVSA-N
InChI
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
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
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
Pharmacology
IndicationLatamoxef 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.
Structured Indications Not Available
PharmacodynamicsLatamoxef works by inhibiting bacterial cell wall biosynthesis.
Mechanism of actionPenicillins 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Penicillin-binding protein 3Proteinyes
inhibitor
Bacillus subtilis (strain 168)P42971 details
Penicillin-binding protein 1AProteinunknown
inhibitor
Escherichia coli (strain K12)P02918 details
Penicillin-binding protein 1BProteinunknown
inhibitor
Escherichia coli (strain K12)P02919 details
D-alanyl-D-alanine carboxypeptidase DacBProteinunknown
inhibitor
Escherichia coli (strain K12)P24228 details
Related Articles
AbsorptionRapidly absorbed after oral administration.
Volume of distribution

8.51 L

Protein binding40%
MetabolismNot Available
Route of eliminationRenal Excretion accounts for 75 %
Half life1.6 hours
ClearanceNot Available
ToxicityLatamoxef 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.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Latamoxef.Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Latamoxef.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71. [PubMed:6217353 ]
  2. 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 ]
External Links
ATC CodesJ01DD06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9253
Blood Brain Barrier-0.9914
Caco-2 permeable-0.7721
P-glycoprotein substrateSubstrate0.7268
P-glycoprotein inhibitor INon-inhibitor0.7989
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.8587
CYP450 2C9 substrateNon-substrate0.7914
CYP450 2D6 substrateNon-substrate0.8291
CYP450 3A4 substrateSubstrate0.5676
CYP450 1A2 substrateNon-inhibitor0.8075
CYP450 2C9 inhibitorNon-inhibitor0.7409
CYP450 2D6 inhibitorNon-inhibitor0.8614
CYP450 2C19 inhibitorNon-inhibitor0.7233
CYP450 3A4 inhibitorInhibitor0.5245
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.684
Ames testNon AMES toxic0.6673
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9144
Rat acute toxicity2.2482 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9759
hERG inhibition (predictor II)Non-inhibitor0.5569
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-0.58BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.751 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
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
  • Phenylpropylamine
  • Phenylacetate
  • Oxacephem
  • Alkylarylthioether
  • Phenol
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Beta-lactam
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azetidine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Enamine
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
pbpC
Uniprot ID:
P42971
Molecular Weight:
74405.915 Da
References
  1. Ishikawa M, Miyauchi T, Yagi K, Chikaishi H, Fukuta Y, Miyake H, Harada M, Yogita S, Tashiro S: Clinical relevance of antibiotic-induced endotoxin release in patients undergoing hepatic resection. World J Surg. 1999 Jan;23(1):75-9. [PubMed:9841767 ]
  2. Labia R, Baron P, Masson JM: Binding of latamoxef (moxalactam) and its decarboxylated derivative to Escherichia coli and Pseudomonas aeruginosa penicillin-binding proteins. J Antimicrob Chemother. 1985 Jan;15(1):9-15. [PubMed:3918982 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:
mrcA
Uniprot ID:
P02918
Molecular Weight:
93635.545 Da
References
  1. Labia R, Baron P, Masson JM: Binding of latamoxef (moxalactam) and its decarboxylated derivative to Escherichia coli and Pseudomonas aeruginosa penicillin-binding proteins. J Antimicrob Chemother. 1985 Jan;15(1):9-15. [PubMed:3918982 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits).
Gene Name:
mrcB
Uniprot ID:
P02919
Molecular Weight:
94291.875 Da
References
  1. Labia R, Baron P, Masson JM: Binding of latamoxef (moxalactam) and its decarboxylated derivative to Escherichia coli and Pseudomonas aeruginosa penicillin-binding proteins. J Antimicrob Chemother. 1985 Jan;15(1):9-15. [PubMed:3918982 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Gene Name:
dacB
Uniprot ID:
P24228
Molecular Weight:
51797.85 Da
References
  1. Labia R, Baron P, Masson JM: Binding of latamoxef (moxalactam) and its decarboxylated derivative to Escherichia coli and Pseudomonas aeruginosa penicillin-binding proteins. J Antimicrob Chemother. 1985 Jan;15(1):9-15. [PubMed:3918982 ]
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Drug created on September 06, 2007 17:50 / Updated on December 08, 2016 11:47