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Clometocillin

Clometocillin, whose tradename is Rixapen  [1] is an anti Gram positive penicillin [2]  indicated for the treatment of respiratory system and skin with streptococci, in dental abscess and in preventing the reappearance of acute articular rheumatism.

Therapeutic use

 

Dosage and Administration

 

Toxicology

 

Pharmacokinetic

 

Absorption

 

Distribution


Excretion

 

Metabolism

 

Mechanism of Action

 

Antibacterial activity

In a study with 21 antibiotics, clometocillin was the most active penicillin against pen-I or pen-R pneumococci [3] (see table 1).

Table 1. Susceptibility of pneumococci to b-lactam antibiotics

Antibiotic n ≤0.008 0.016 0.03 0.06 0.12 0.25 0.5 1 2 4 8
penicillin G                        
pen-S 283 43.8 90.1 99.3 100              
 pen-I 122
 
        7.4 13.9 29.5 100      
pen-R 23                 100    
clometocillin                        
pen-S 210 60.9 95.7 97.6 98.1 100            
 pen-I 122       0.8 13.9 24.6 94.3  100      
pen-R 23             47.8 100      
ampicillin                        
pen-S 283 14.5 33.2 64 98.2  98.6 100          
 pen-I 122       0.8 9 13.1 13.9 18.8 35.2 94.2 100
pen-R 23                   30.4 100
amoxycillin                        
pen-S 283 17.3 77.7 98.2 98.5 99.6 100          
 pen-I 122     1.6 8.2  12.3 17.2 25.4 49.2 94.3 100  
pen-R 23                 52.2 100  
piperacillin                        
pen-S 283 4.2 21.9 89.4 97.2 97.9 99.3 100        
 pen-I 122           6.6  11.5  18  41  98.4 100
pen-R 23                   91.3 100
imipenem                        
pen-S 283 96.1 98.9 99.3 100              
 pen-I 122 1.6 7.4 13.9 23.8 66.4 97.5 100        
pen-R 23         4.3 86.9 100        
meropenem                        
pen-S 283 79.5 98.2 99.6 99.6 100            
 pen-I 122   4.1 9.8 13.1 16.4 62.3 95.1 100      
pen-R 23             100        
cephradine                        
pen-S 283         2.8 5.6 17.3  95.4 98.9 100  
 pen-I 122             0.8 4.1 8.2 10.7 16.4
pen-R 23                      
cefadroxil                        
pen-S 283         2.5 28.6 56.2 98.2 100    
 pen-I 122               4.9 9 10.8 16.4
pen-R 23                      
cefaclor                        
pen-S 283         37.8 92.9 99.6  100      
 pen-I 122             5.7 10.7 11.5 17.2 19.7
pen-R 23                      
cefatrizine                        
pen-S 283   2.8 12.4 77.4  96.8 98.6 100        
 pen-I 122         0.8 8.2 13.9 17.2  23.8 52.5 86.9
pen-R 23                   8.7 47.8
cefuroxime                        
pen-S 283 30.7 83 92.2 97.5 100            
 pen-I 122       1.6 3.3 11.5 16.4 20.5 46.7 97.5 100
pen-R 23                   91.8 100
cefpodoxime                        
pen-S 283 11.6 59.7 95.4 97.9 99.6 100          
 pen-I 122       0.8 9.8 12.3 14.7 33.6 89.3 100  
pen-R 23                 26.1 95.6 100
cefetamet                        
pen-S 283         9.2 59.7 80.6 98.6 99.6 100  
 pen-I 122             0.8 9 13.1 13.9 17.2
pen-R 23                      
cefixime                        
pen-S 283         31.1 37.2 64.6 91.1 98.6 100  
 pen-I 122           0.8 0.8 6.8 11.1 12.8 23.1
pen-R 23                      
ceftibuten                        
pen-S 283               24.8 58.3 93.3 96.8
 pen-I 122                      
pen-R 23                      
cefotaxime                        
pen-S 283 43.1 90.5 98.9 100              
 pen-I 122     0.8 10.7 12.3 23.8 55.7 99.2 100    
pen-R 23             4.3 82.6 100    
ceftriaxone                        
pen-S 283 59.4 90.1 97.5 99.3 100            
 pen-I 122     2.5 9.8 11.5 16.4 77.9 99.2 100    
pen-R 23           4.3 17.4 95.6 100    
cefpirome                        
pen-S 283 16.2 85.9 94.7 100              
 pen-I 122     2.5 8.2 13.1 37.7 99.2 100      
pen-R 23             78.3 95.6 95.6 100  
cefepime                        
pen-S 283 4.6 55.1 90.5 98.6 99.6 100          
 pen-I 122     0.8 5.7 9.8 14.7 41.8 98.3 100    
pen-R 23             82.6 100      
ceftazidime                        
pen-S 283     0.5 6.7 39.5 90.5 98.6 99 100    
 pen-I 122           0.8 1.6  1.6 15.6 16.4 25.4
pen-R 23                      

Other pharmacological effects

 


Medicinal Chemistry

CAS number:  1926-49-4  EINECS: 217-657-6
 

Molecular Formula: C17H18Cl2N2O5S

Average mass:  433.306213 Da

Monoisotopic mass: 432.031342 Da

Systematic name: (2S,5R,6R)-6-{[(3,4-Dichlorophenyl)(methoxy)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC(=C(C=C3)Cl)Cl)OC)C(=O)O)C

Std. InChI: 1S/C17H18Cl2N2O5S/c1-17(2)12(16(24)25)21-14(23)10(15(21)27-17)20-13(22)11(26-3)7-4-5-8(18)9(19)6-7/h4-6,10-12,15H,1-3H3,(H,20,22)(H,24,25)/t10-,11?,12+,15-/m1/s1
 

ACD/LogP: 2.630.32 # of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): -0.35 ACD/LogD (pH 7.4): -1.10
ACD/BCF (pH 5.5): 1.00 ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 5.5): 1.00 ACD/KOC (pH 7.4): 1.00
#H bond acceptors: 7 #H bond donors: 2
#Freely Rotating Bonds: 5 Polar Surface Area: 121.24 2
Index of Refraction: 1.653 Molar Refractivity: 102.30.4 cm3
Molar Volume: 279.75.0 cm3 Polarizability: 40.60.5 10-24cm3
Surface Tension: 69.55.0 dyne/cm Density: 1.50.1 g/cm3
Flash Point: 373.031.5 C Enthalpy of Vaporization: 106.63.0 kJ/mol
Boiling Point: 693.155.0 C at 760 mmHg Vapour Pressure: 0.02.3 mmHg at 25C

 

 

Major Impurities:

Appearance:

Melting point:

Optical rotation: [a]D +210-220. The free acid yields two diastereoisomers: [a]D +177 and [a]D +257.

Solubility:

Stability:

 


1. Vanderhaeghe et al., "Semi-synthetic antibiotic related to penicillin".  Antimicrob. Agents Chemother. 581, (1961).

2. van Dijck et al., Antibiot. Chemother. 12, 192, (1962).

3. Verhaegen J., Verbist L. "In-vitro activity of 21 b-lactam antibiotics against penicillin-susceptible and penicillin-resistant Streptococcus pneumoniae". J. Antimicrob. Chemother. 41, 381385, (1998).

 

 

 

 

 

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