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Moxalactam

CHEMBL74632 Phase 4 Đã phê duyệt Small molecule
Half-Life
—
Bioavailability
—
Protein Binding
—
Molecular Weight
520.5 g/mol
LogP
-0.6
Phase
4

An oxacephem nucleus rather than the usual cephem ring sets moxalactam apart from the other third-generation cephalosporins, and that structural variation shaped both its spectrum and its downfall. Activity extended usefully across gram-negative organisms and anaerobes, a combination that was uncommon at the time of its introduction. The agent also interfered with vitamin K-dependent clotting factor synthesis, and the resulting serious bleeding episodes proved decisive: safer cephalosporins and other antibacterial agents have largely displaced it from practice. Its history is frequently cited when the haemostatic effects of the N-methylthiotetrazole side chain are discussed. The compound has the formula C20H20N6O9S and a molecular weight near 520.5 g/mol, and reached the final phase of clinical development.

This third-generation cephalosporin antibiotic with unusual oxacephem structure had good activity against gram-negative bacteria and anaerobes but was associated with serious bleeding problems due to interference with vitamin K-dependent clotting factors. It has been largely replaced by safer cephalosporins and other antibiotics.

Khối lượng phân tử

520,5000 g/mol

LogP

-0,60

TPSA

232,00 Ų

Lipinski RO5

Không đạt

Lĩnh vực điều trị

Infectious Disease

Cơ chế tác dụng

An oxacephem (1-oxa-beta-lactam) antibacterial. Moxalactam binds penicillin-binding proteins and blocks the transpeptidation step that cross-links peptidoglycan, leaving a defective cell wall that fails under osmotic stress. Its N-methylthiotetrazole side chain separately interferes with vitamin K-dependent clotting factor synthesis and with platelet function, which is the origin of the bleeding that led to its withdrawal.

Pharmacokinetics (PK)

Pharmacodynamics (PD)

Cơ chế

An oxacephem (1-oxa-beta-lactam) antibacterial. Moxalactam binds penicillin-binding proteins and blocks the transpeptidation step that cross-links peptidoglycan, leaving a defective cell wall that fails under osmotic stress. Its N-methylthiotetrazole side chain …

Cấu trúc 2D

SVG PNG

Cite this structure


                        

                            
                            
                        

                    

                


                
                

                    

                    

                        
Embed this structure

                        

                        

                            
                            
                        

                    

                

                

                
                

                    
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

                

                

                
                

                    
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

                

                

                

                    
                    

                        
Molecular Formula

                        
C20H20N6O9S

                    

                    
                    

                        
HBD / HBA

                        
4 / 13

                    

                    
                    

                        
Liên kết có thể quay

                        
9

                    

                    
                    
                    

                        
Nguyên tử nặng

                        
36

                    

                    
                

            


            
            

                
                


    
    
        
    
    
    
No targets recorded

    
    
Target interaction data is not yet available for this drug.

    



                
            


            
            

                
                


    
    
        
    
    
    
No interactions recorded

    
    
Drug interaction data is not yet available for this compound.

    



                
            


            
            

                
                


    
    
        
    
    
    
No side effects recorded

    
    
Side effect data is not yet available for this drug.

    



                
            


            
            
            

                
Câu hỏi thường gặp

                

                    
                    

                        
                        

                            
This third-generation cephalosporin antibiotic with unusual oxacephem structure had good activity against gram-negative bacteria and anaerobes but was associated with serious bleeding problems due to interference with vitamin K-dependent clotting factors. It has been largely replaced by safer cephalosporins and other antibiotics.

                        

                    

                    

                    

                    
                    

                        
                        

                            
An oxacephem (1-oxa-beta-lactam) antibacterial. Moxalactam binds penicillin-binding proteins and blocks the transpeptidation step that cross-links peptidoglycan, leaving a defective cell wall that fails under osmotic stress. Its N-methylthiotetrazole side chain separately interferes with vitamin K-dependent clotting factor synthesis and with platelet function, which is the origin of the bleeding that led to its withdrawal.

                        

                    

                    

                    

                    

                        
                        

                            
Yes, Moxalactam is an approved drug. It has reached clinical phase 4. It is classified as a Small molecule.

                        

                    

                

            

            

            
            

            
            

            
            
{# References & Data Sources section for drug detail pages.
   Renders standard pharmacological database links plus the drug's data_sources field. #}


    
References & Data Sources

    
    
        
        
  • 
            
            
                ChEMBL — European Bioinformatics Institute (EBI).
                CHEMBL74632.
                Open-access bioactivity database.
            
        
    • 
        
        
        
  • 
            
            
                PubChem — National Center for Biotechnology Information (NCBI).
                CID 47499.
                Chemical information database.
            
        
    • 
        
        
        
        
    

    
Data aggregated from publicly available pharmacological databases. Last updated 2026-08-20.




        


        
        
    


    



    
Tuyên bố miễn trách y tế

    

        This content is for educational and informational purposes only. It is not a substitute for professional medical advice, diagnosis, or treatment. Always consult a qualified healthcare provider before making medication decisions.
    

    

        Data sources:
        ChEMBL,
        PubChem,
        DailyMed.