Soluble Steroids I: Sugar Derivatives

Glucamine, glucosamine, and N-methylglucamine derivatives of cholesterol, testosterone, 9-α-fluorohydrocortisone, triamcinolone acetonide, and hexestrol have been synthesized in an attempt to provide compounds with increased aqueous solubility. The acylable hydroxy group of the steroid was converted to the chloroformate and then condensed with the appropriate amino sugar. In general, the derivatives which have been prepared possess 8 to 13 times the aqueous solubility of the parent compounds. The N-methylglucamine and glucosamine derivatives of triamcinolone acetonide, when applied topically, failed to show appreciable pharmacological activity.