Home
Up

Thiamphenicol

Thiamphenicol is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times more potent. It is insoluble in water, but highly soluble in lipids. Thiamphenicol is used in many countries as a veterinary antibiotic, but is available in China and Italy for use in humans. Its main advantage over chloramphenicol is that it has never been associated with aplastic anaemia.

Unlike chloramphenicol, thiamphenicol is is not readily metabolized in cattle, poultry, sheep, or humans, but is predominantly excreted unchanged.

Therapeutic use

 

Toxicology
 

 

Pharmacokinetic

 

Bioavailability  
Metabolism hepatic
Half-life 5.0 hrs
Excretion renal

 

 


Medicinal Chemistry

CAS number: 15318-45-3  EINECS:

Molecular Formula: C12H15Cl2NO5S

Average mass: 356.222 Da
Monoisotopic mass: 355.00479 Da

Systematic name: 2,2-Dichloro-N-{(1R,2R)-1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]-2-propanyl}acetamide
SMILES: ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CO

Std. InChI: 1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1

Properties
Melting Point: 166 C

ACD/LogP: -0.27 # of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): -0.27 ACD/LogD (pH 7.4): -0.27
ACD/BCF (pH 5.5): 1.00 ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 5.5): 16.99 ACD/KOC (pH 7.4): 16.98
#H bond acceptors: 6 #H bond donors: 3
#Freely Rotating Bonds: 8 Polar Surface Area: 112.08 2
Index of Refraction: 1.583 Molar Refractivity: 79.785 cm3
Molar Volume: 238.767 cm3 Polarizability: 31.629 10-24cm3
Surface Tension: 58.7719993591309 dyne/cm Density: 1.492 g/cm3
Flash Point: 374.652 C Enthalpy of Vaporization: 107.03 kJ/mol
Boiling Point: 695.875 C at 760 mmHg Vapour Pressure: 0 mmHg at 25C

 

 

 

     Hit Counter 

 

Send mail to stefano.biondi@innovativesolution.it with questions or comments about this web site.
Copyright 2010 Innovative Solution di Biondi Stefano