HSP Application note #27
Hansen Solubility Parameter (HSP) and Sulfa Drug2010.3.29
HSPiP Team Senior Developer, Dr. Hiroshi Yamamoto
Sulfa drug:
Sulfonamide and related compounds are used for Antimicrobial.
I got the HPLC data and simulated with HSP.
Hansen Solubility Parameters (HSP)Hansen Solubility Parameters(HSP) were developed by Charles M. Hansen as a way of predicting if one material will dissolve in another and form a solution. They are based on the idea that "like dissolves like" where one molecule is defined as being 'like' another if it bonds to itself in a similar way. What can perhaps be surprising is that one can assign HSP to so many different things. Gases like carbon dioxide, solids like carbon-60, sugar, and biological materials like human skin, depot fat, DNA, and even some proteins all have HSP. The list can be continued with drugs, polymers, plasticizers, and in fact any organic material and even many inorganic materials like salts. The only requirement for an experimental confirmation is that the material must behave differently in a sufficient number of test solvents upon contact. Pirika JAVA Demo Applet calculate HSP. HSPLight is available here. |
No | name | CAS# | Hcode | RT |
1 | sulfaguanidine | 57-67-0 | 21896 | 5.419 |
2 | sulfanilamide | 63-74-1 | 1077 | 5.614 |
3 | sulfacetamide | 144-80-9 | 21897 | 10.027 |
4 | sulfadiazine | 68-35-9 | 21898 | 12.3 |
5 | sulfathiazole | 72-14-0 | 21899 | 13.226 |
6 | sulfapyridine | 144-83-2 | 21900 | 13.513 |
7 | sulfamerazine | 127-79-7 | 21901 | 14.637 |
8 | trimethoprim | 738-70-5 | 20465 | 15.176 |
9 | sulfamethizole | 144-82-1 | 21902 | 16.395 |
10 | sulfadimidin | 57-68-1 | 21903 | 16.686 |
11 | sulfamethoxypyridazine | 80-35-3 | 21904 | 17.033 |
12 | sulfachloropyridazine | 80-32-0 | 21905 | 17.744 |
13 | sulfamethoxazole | 723-46-6 | 21906 | 18.08 |
14 | sulfamonomethoxine | 1220-83-3 | 21907 | 18.73 |
15 | sulfadoxine | 2247-57-6 | 21908 | 19.502 |
16 | sulfabenzamide | 127-71-9 | 21909 | 20.482 |
17 | sulfadimethoxine | 122-11-2 | 21910 | 22.877 |
18 | sulfaquinoxaline | 59-40-5 | 21911 | 23.807 |
19 | sulfanitran | 122-16-7 | 21912 | 27.051 |
ChromatographyThe most popular column for HPLC is ODS column and this column contains Silica-gel covered by Octadecyl. When we insert some chemicals into this column, some chemicals dissolve to octadecyl alkyl chain deeply and some do not. So, highly interacted chemicals will delay to elute. Or some chemicals which are very easily dissolve to carrier liquid, elute very early. We can evaluate these solubility with Hansen Solubility Parameters (HSP). Molecular size also play important role. Pirika Java Demo Applet design Carrier Solvent. HPLCDemo is available here. |
I do not know why No.8 compound is here.
The Gradient of solvent is very complicated, so correlation is not so beautiful.
If you draw several molecules and calculate each molecules' properties, program will simulate Retention Time (RT) of OSD column for HPLC. If you want to know how to draw molecules, please refer to PowerTools applications. I have full version of this HPLC RT simulation program at PowerTools+ Applications.
HSP DistanceTo calculate the distance (Ra) between Hansen parameters in Hansen space the following formula is used: HSP distance(Ra)={4*(dD1-dD2)2 + (dP1-dP2)2 +(dH1-dH2)2 }0.5 |
But distance from Octadecane(OD) become long, that means difficult to dissolve to OD, the compounds elute early.
I got another HPLC data for Antimicrobials.
This case is mixture of several kind of Drugs.
No.8 and No.11 compounds are so bad.
Actually, HSP estimation itself very bad.
For such a large molecules that have a lot of functional groups, Y-MB result is very bad.
In that case, you would better break compound into several parts and make average.
Even though, if you get reliable HSP, HPLC simulation result will still poor.
If the molecular size are so different, we can not compare with retention time.
And No.9, maybe HSP estimation result is very bad.
We need to fix in version 4.
Retention time for HPLC
HPLC analysis of PAHs
HPLC analysis of medicine of Epilepsia
HPLC analysis of Anti-oxidant.
HPLC analysis of Sulfa Drugs.
HPLC analysis of Plasticizer