In order to increase the stability and dispersibility of drugs and to decrease their irritant properties, attempts were made to give surface-active properties to the main drugs.Higher alkyl sulfates of antihistamines like Ph₂CHOCH₂CH₂NMe₂ (I), antimicrobial agents like 2-dimethylamino-6-(2-diethylaminoethoxy)benzothiazole (II), and local anesthetics like procaine (III) were synthesized and their surface tension was measured.Also, emulsification tests were carried out.They had better surface activity than the free bases, HCl salt, and other inorganic acid salts.The surface activity and emulsifiability became the greatest when the number of C atoms in the alkyl group of the alkyl sulfates was 12-14.A good result was obtained in the emulsification of liquid paraffin and water by the use of dodecyl sulfate (IV) of I with the addition of a min. amount of alkali.I-HCl (29.2 g.) in 50 mL. water treated dropwise with 28.8 g. Na dodecyl sulfate in 150 mL. water, the solution kept standing, and the product extracted with Et₂O gave I-dodecyl sulfate.Similarly, 3.7 g. II-HCl in 30 mL. water and 6.3 g. Na tetradecyl sulfate in 50 mL. water, mixed, filtered, dried, and extracted with dry C₆H₆ gave II-ditetradecyl sulfate.Waxy products of procaine-octadecyl sulfate and p-BuNHC₆H₄CO₂CH₂CH₂NMe₂-dodecyl sulfate were also prepared

01 Jan 1957·YAKUGAKU ZASSHI

Surface Activation of Medicines. II

Author: Murakumo, Naomasa ; Usuki, Takashi ; Tanaka, Nobuo ; Sato, Yoshishige ; Harada, Kiyoshi ; Utsumi, Isamu

Na dodecyl sulfate (5.7 g.) in 100 ml. warm water treated with 3.4 g. thiamine-HCl (I) in 100 ml. water, cooled slowly, and the product recrystallized from 95% Me₂CO gave 6.8 g. thiamine-didodecyl sulfate, m. 82-4°.Similarly are prepared thiamine-ditetradecyl sulfate-hydrate, m. 85-7°, and thiamine-dihexadecyl sulfate-H₂O, m. 88-90°.Thiamine chloride (II) (3.1 g.) in 20 ml. water added dropwise into 2.8 g. Na dodecyl sulfate in 20 ml. warm water and the product recrystallized from 80% Me₂CO gave 2.4 g. thiamine-monododecyl sulfate (III), m. 98-101°.Or, 3.6 g. Ag dodecyl sulfate in 30 ml. warm water treated with 3.1 g. II in 20 ml. water, the AgCl centrifuged off, the aqueous solution concentrated in N, the residue in MeOH filtered, the filtrate treated with Et₂O, and the precipitate recrystallized from Me₂CO gave 3.4 g. III, m. 99-101°.Similarly were prepared thiamine-monotetradecyl sulfate, m. 102-4°, and thiamine-monohexadecyl sulfate, m. 104-9°.The linkage between the thiamine and higher alkyl sulfate is an ionic bond as in the salts.They form a micelle in aqueous solution and indicate a strong surface activity.With increasing number of C atoms in the alkyl group, the salts become progressively in soluble in water at room temperature and become soluble in some organic solvents, such as alcs. and CHCl₃.These alkyl sulfates are less bitter and of characteristic odor than the known salts and are more stable.

Yakugaku Zasshi

Surface activation of medicinals. VIII. Properties of alkyl sulfate medicinals. 3. Solubility and Krafft's phenomenon

Author: Harada, Kiyoshi

cf. CA 57, 6029i.Difference in the solubility of alkyl sulfates of various amino compounds in EtOH, BuOH, CHCl₃, and H₂O was examinedSolubility in a certain solvent is affected by the counter ion.In general, these alkyl sulfates have greater affinity to these solvents than mineral acid salts and become very sparingly soluble in H₂O below the Krafft point (K.p.) with increasing number of C atoms in the straight alkyl chain.The Krafft phenomenon in aqueous C_1-4 alc. was examined; the K.p. decreased in proportion to concentration of alc., as was observed earlier in the case of thiamine alkyl sulfates, and a linear relation existed between the logarithm of the lowering of the K.p. and the number of C atoms in the alc.Alkyl sulfates of quinine and tetracycline, whose K.ps. in aqueous solution were too high to be measured, showed clear K.ps. in alc. solutionThe K.ps. of the alkyl sulfates of amines became higher with increasing number of C atoms in the straight alkyl chain.In these alkyl sulfates, lowering of the K.p. and concentration of alc. were not linear and the K.p. decreased suddenly after a certain concentration

100 Deals associated with Diphenhydramine laurylsulfate

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Indication	Country/Location	Organization	Date
Eczema	Japan	Mitsubishi Tanabe Pharma Corp.	01 Oct 1950
Insect Bites and Stings	Japan	Mitsubishi Tanabe Pharma Corp.	01 Oct 1950
Measles	Japan	Mitsubishi Tanabe Pharma Corp.	01 Oct 1950
Pruritus	Japan	Mitsubishi Tanabe Pharma Corp.	01 Oct 1950

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