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Prodrug name : Chloramphenicol palmitate
PDID : PDIDC038
Activating enzyme : Pancreatic esterases in the small intestine
Mode of activation : Hydrolysis

Indication : Bacterial infection

Target : 50S ribosomal subunit
Properties improved : Improved taste (R3)
Structure
Prodrug Active compound
Chloramphenicol palmitate
Experimental pharmacokinetic properties

Prodrug
Dose : Na
Ae : Na
Cmax : Na
Tmax : Na
Bioavailability(%F) : Approximately 80 (R1)
Plasma Protein Binding(%PPB) : Na
Volume of distribution(Vd) : Na

Active compound
Experimental solubility and lipophilicity
LogP : Na
Solubility : Na
Predicted properties (SwissADME)

Physicochemical Properties

Prodrug
Formula : C27H42Cl2N2O6
Molecular weight : 561.54
Num. heavy atoms : 37
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.7
Num. rotatable bonds : 23
Num. H-bond acceptors : 6
Num. H-bond donors : 2
Molar Refractivity : 151.41
Plasma TPSA : 121.45

Active compound

Lipophilicity

Prodrug
Log Po/w (iLOGP) : 3.92
Log Po/w (XLOGP3) : 9.04
Log Po/w (WLOGP) : 6.62
Log Po/w (MLOGP) : 3.54
Log Po/w (SILICOS-IT) : 6.06
Consensus Log Po/w : 5.84

Active compound

Water Solubility

Prodrug
Log S (ESOL) : -7.62
Solubility : 0.0000135; 2.41E-08
Class : Poorly soluble
Log S (Ali) : -11.48
Solubility : 1.85E-09; 3.29E-12
Class : Insoluble
Log S (SILICOS-IT) : -8.47
Solubility : 0.00000188; 3.35E-09
Class : Poorly soluble

Pharmacokinetics

Prodrug
GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes; 3.35E-09
Log Kp (skin permeation) : -3.31

Druglikeness

External web links (WL)

1) https://www.drugbank.ca/drugs/DB14658; 2) http://www.genome.jp/dbget-bin/www_bget?drug:D01072; 3) http://www.chemspider.com/Chemical-Structure.391613.html; 4) http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL1506; 5) https://pubchem.ncbi.nlm.nih.gov/compound/443382

References (R)

1) doi:10.2165/00003088-198409030-00004; 2) doi:10.4103/0250-474X.40334; 3) doi:10.2174/1874104501711010146; 4) doi:10.1093/toxsci/kfq085