Benzodiazepines salt?

[sekio]

source: chemicalize.org

The bottom graph is what you want, logD, e.g. solubility in fat versus pH. Lower = more soluble in water. The top shows the species that exist at each pH. As midazolam is acidified, two different sites get protonated and pick up a positive formal charge, which increases water solubility. (most salts/ion pairs are much more polar and hence more water soluble than neutral organic compounds.) At biological pH (7.4) it is fat soluble though, which is what you want in a drug. But it also means it will have poor solubility in water at neutral pH.

Midazolam hydrochloride solution is equivalent to dissolving midazolam free base into dilute hydrochloric acid. They're the same thing, chemically speaking.

Chemicalize is a good tool to play with, you can predict water solubility to within some margin of error of pretty much any compound you can think of.

 

[clubcard]

+1 on Chemicalize. Could I also add MarvinSketch - the site has pKa and such.

 

[lolwhatzdrugs]

Coolest info eva +2

 

[Hœlsämmen Hātbhůt Fhűkærï]

I think if you made a water-soluble version of alprazolam, you'd fuck the world over with a new pandemic..

At least nobody would remember much about it…

 

[4DQSAR]

Chlorazipate dipotassium (Traxene™/Tranquil™).

It's a prodrug with decarboxylation yielding nordiazepam.

I see no reason why this class of prodrug could not provide an entirely new class of RCs. The only limitation being those 1,4-benzodiazepines that contain a 3-OH moiety.