Identification
- Generic Name
- Latamoxef
- DrugBank Accession Number
- DB04570
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Latamoxef (DB04570)
- Weight
- Average: 520.473
Monoisotopic: 520.101246958 - Chemical Formula
- C20H20N6O9S
- Synonyms
- Festamoxin
- Lamoxactam
- Latamoxef
- Latamoxefum
- Moxalactam
Pharmacology
- 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.
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Latamoxef 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.
Target Actions Organism APenicillin-binding protein 3 inhibitorBacillus subtilis (strain 168) UPenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) UPenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) UD-alanyl-D-alanine carboxypeptidase DacB inhibitorEscherichia coli (strain K12) - Absorption
Rapidly absorbed after oral administration.
- Volume of distribution
8.51 L
- Protein binding
40%
- Metabolism
- Not Available
- Route of elimination
Renal Excretion accounts for 75 %
- Half-life
1.6 hours
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Latamoxef may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Latamoxef. Aceclofenac The risk or severity of nephrotoxicity can be increased when Latamoxef is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Latamoxef is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Latamoxef is combined with Acenocoumarol. Acetaminophen Latamoxef may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Latamoxef. Aclidinium Latamoxef may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Latamoxef may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Latamoxef. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Latamoxef disodium 5APW73W3QZ 64953-12-4 GRIXGZQULWMCLU-HUTAOCTPSA-L
Categories
- ATC Codes
- J01DD06 — Latamoxef
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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 show 9 more
- Substituents
- 1,3-dicarbonyl compound / 1-hydroxy-2-unsubstituted benzenoid / Alkylarylthioether / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole / Benzenoid / Beta-lactam show 26 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, oxacephem (CHEBI:599928)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- VUF6C936Z3
- CAS number
- 64952-97-2
- InChI Key
- JWCSIUVGFCSJCK-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
References
- General References
- Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015574
- KEGG Drug
- D08109
- KEGG Compound
- C07231
- PubChem Compound
- 47499
- PubChem Substance
- 46505546
- ChemSpider
- 43215
- BindingDB
- 50370589
- 7069
- ChEBI
- 599928
- ChEMBL
- CHEMBL74632
- Therapeutic Targets Database
- DAP001181
- PharmGKB
- PA164743144
- Wikipedia
- Latamoxef
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count Not Available Recruiting Not Available Children；Infection 1 Not Available Recruiting Not Available Neonatal Early Onset Sepsis 1 Not Available Unknown Status Not Available Community Acquired Pneumonia (CAP) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -0.58 BIOBYTE (1995) - Predicted Properties
Property Value Source Water Solubility 0.751 mg/mL ALOGPS logP 0.22 ALOGPS logP 0.17 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 2.81 Chemaxon pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 206.3 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 133.7 m3·mol-1 Chemaxon Polarizability 47.27 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9253 Blood Brain Barrier - 0.9914 Caco-2 permeable - 0.7721 P-glycoprotein substrate Substrate 0.7268 P-glycoprotein inhibitor I Non-inhibitor 0.7989 P-glycoprotein inhibitor II Inhibitor 0.5 Renal organic cation transporter Non-inhibitor 0.8587 CYP450 2C9 substrate Non-substrate 0.7914 CYP450 2D6 substrate Non-substrate 0.8291 CYP450 3A4 substrate Substrate 0.5676 CYP450 1A2 substrate Non-inhibitor 0.8075 CYP450 2C9 inhibitor Non-inhibitor 0.7409 CYP450 2D6 inhibitor Non-inhibitor 0.8614 CYP450 2C19 inhibitor Non-inhibitor 0.7233 CYP450 3A4 inhibitor Inhibitor 0.5245 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.684 Ames test Non AMES toxic 0.6673 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 0.9144 Rat acute toxicity 2.2482 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9759 hERG inhibition (predictor II) Non-inhibitor 0.5569
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 74405.915 Da
References
- 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. [Article]
- 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. [Article]
- 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 str...
- Gene Name
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- 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. [Article]
- 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 str...
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- 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. [Article]
- 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
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacB
- Molecular Weight
- 51797.85 Da
References
- 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. [Article]
Drug created at September 06, 2007 23:50 / Updated at May 07, 2021 21:42