From: Richard Prankerd (richard$##$pharmacy.uq.edu.au)
Date: Tue Nov 30 1999 - 05:00:15 EST
In response to the emails from Jacob and Ulrich:
The following paper gives the salt-forming acids that had FDA
acceptability at the time of publication: Berge, SM, Bighley LD and
Monkhouse DC, Pharmaceutical salts. J.Pharm.Sci., 66(1), 1-19 (1977).
These are:
acetic, benzenesulfonic, benzoic, bicarbonic, bitartaric, calcium
dihydrogenedetic, camphorsulfonic, carbonic, citric, edetic,
1,2-ethanedisulfonic, estolic (laurylsulfuric), ethanesulfonic,
fumaric, glucoheptonic, gluconic, glutamic, glycollylarsanilic,
hexylresorcinic, hydrabamine (N,N'-di(dehydroabietyl)ethanediamine),
hydrobromic, hydrochloric, hydroxynaphthoic, hydriodic,
2-hydroxyethanesulfonic, lactic, lactobionic, malic, maleic,
mandelic, methanesulfonic, mucic, naphthalenesulfonic, nitric, pamoic
(embonic), pantothenic, phosphoric, polygalacturonic, salicylic,
stearic, subacetic, succinic, sulfuric, tannic, tartaric, theoclic
(8-chlorotheophyllinic), triethiodic.
Others have no doubt been approved since 1977, but I do not have an
up to date list.
Other non-FDA approved acids which are used in other countries are
also reported in the paper: adipic, alginic, aminosalicylic,
anhydromethylenecitric, arecoline, aspartic, hydrogensulfuric,
camphoric, digluconic, hydrogensuccinic, glycerophosphoric,
hydrofluoric, methylenebis(salicylic), napadisylic
(1,5-naphthalenedisulfonic), oxalic, pectinic, persulfuric,
phenylethylbarbituric, picric, propionic, thiocyanic,
toluenesulfonic, undecanoic
It should be noted that oxalic acid (in Ulrich's list) is not
acceptable to the FDA - it has some toxicity, presumably due to its
ability to chelate calcium.
It should also be noted that some of the acids in the above lists
(e.g., hydroxynapthoic, napadisylic, naphthalenesulfonic, pamoic) are
intended to reduce water solubility, rather than increase it. The
paper notes numerous other salt-forming acids with potential for
pharmaceutical use.
Regards
Richard
Richard J. Prankerd, PhD
Senior Lecturer Phone: INT + (617) 3365-3179
School of Pharmacy Fax: INT + (617) 3365-1688
University of Queensland richard$##$uqpharmacy.pharmacy.uq.edu.au
St Lucia QLD 4072 http://www.uq.edu.au/pharmacy/academic.html
AUSTRALIA
DRUGS NEED TO BE DESIGNED WITH DELIVERY COMPONENTS IN MIND - TAKERU HIGUCHI
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