81-13-0

Manufacturing Process

130 parts by weight of d(-)-α-hydroxy-β,β-dimethyl-gamma-butyric acid lactone are dissolved in 150 parts by volume of methyl alcohol. 75 parts by weight of 3-hydroxypropylamine are added, in one portion, to the solution and the mixture is well stirred. While the reaction sets in, the temperature of the mixture gradually rises by itself to about 50°C and then drops again after about two hours. To cause completion of the reaction, the mixture is allowed to stand at room temperature for 24 hours. The so obtained (d+)-α,γdihydroxy-β,β-dimethyl-butyric-acid-(3'-hydroxypropyl)-amide is freed from methyl alcohol in vacuo. It is a colorless, viscous oil, easily soluble in water. It boils under a pressure of 0.02 mm between 118° and 120°C.

Therapeutic Function

Gastrointestinal drug

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

D-Panthenol is the alcohol analogue and biological precursor of D-pantothenic acid. These analogues are precursors in the biosynthesis of coenzyme A. D-Panthenol and D-Pantothenic acid are used in a variety of skin protection products. D-pantothenic acid may have a role in controlling keratinocyte proliferation and differentiation. D-Panthenol may be used for studies of skin protection emulsions from UV irradiation and as a humectant.

Contact allergens

Pan(to)thenol is the alcohol corresponding to pantothenic acid, of the vitamin B5 group. It is used as a food additive, and in skin and hair products as a conditioning agent. Contact dermatitis and urticaria have been reported.

Safety Profile

Moderately toxic by intravenous route. A skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also AMIDES.

Veterinary Drugs and Treatments

Dexpanthenol has been suggested for use in intestinal atony or distension, postoperative retention of flatus and feces, prophylaxis and treatment of paralytic ileus after abdominal surgery or traumatic injuries, equine colic (not due to mechanical obstruction) and any other condition when there is an impairment of smooth muscle function. Controlled studies are lacking with regard to proving the efficacy of the drug for any of these indications.

Purification Methods

Purify D-panthenol by distillation in vacuo. It is a slightly hygroscopic viscous oil and is soluble in H2O and organic solvents. It is hydrolysed by alkali and strong acid. [Rabin J Am Pharm Assoc (Sci Ed) 37 502 1948, Bonati & Pitré Farmaco Ed Scient 14 43 1959, Beilstein 4 IV 1652.]

Brand name

D-Panthenol 50 (BASF); Ilopan (Savage); Motilyn (Abbott).

General Description

Dexpanthenol is an alcohol analog of pantothenic acid and an important component of parenterals, local cosmetic preparations and multi-vitamins. It has as much biological activity as pantothenic acid and is found to be stable in aqueous solution.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.