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Azidocillin

Azidocillin is a penicillin antibiotic similir to ampicillin.

Therapeutic use

For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptocci.

Dosage and Administration

 

Toxicology

 

Pharmacokinetic

Bioavailability  
Protein binding  
Metabolism  
Half-life  
Cmax (mg/ml)  
tmax (hrs)  
Distribution volume Vd (l/kg)  
Clearance  
Excretion  

Absorption

 

Distribution


Excretion

 

Metabolism

 

Mechanism of Action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Azidocillin inhibits 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 Azidocillin interferes with an autolysin inhibitor.

Other pharmacological effects

 


Medicinal Chemistry

CAS number: 17243-38-8    EINECS: 241-278-5

Molecular Formula: C16H18N5O4S

Average mass:   375.402313 Da

Monoisotopic mass: 375.100128 Da

Systematic name: (2S,5R,6R)-6-{[(2R)-2-Azido-2-phenylacetyl]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@@H](C3=CC=CC=C3)N=[N+]=[N-])C(=O)O)C

Std. InChI: 1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1

ACD/LogP: 2.310.34 # of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): -0.67 ACD/LogD (pH 7.4): -1.42
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: 9 #H bond donors: 2
#Freely Rotating Bonds: 5 Polar Surface Area: 124.37 2
Index of Refraction:   Molar Refractivity: cm3
Molar Volume: cm3 Polarizability: 10-24cm3
Surface Tension: dyne/cm Density: g/cm3
Flash Point: C Enthalpy of Vaporization: kJ/mol
Boiling Point: C at 760 mmHg Vapour Pressure: mmHg at 25C

 

Major Impurities:

Appearance:

Melting point:

Optical rotation:

Solubility:

logP: 2.65

pKa:

Stability:

 

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