Dexpanthenol

Absorption

Dexpanthenol is soluble in water and alcohol, although insoluble in fats and oil based substances. With the appropriate vehicle, Dexpanthenol is easily penetrated into the skin. Rate of penetration and absorption is reduced when Dexpanthenol is administered as an oil/water formula.

Toxicity

Mouse LD50 : 9gm/kg (Intraperitoneal) Mouse: LD50 7gm/kg (Intravenous) Mouse: LD50 15gm/kg (Oral) Rabbit LD50 4gm/kg (Oral)

Chemical properties

clear colorless to slightly yellow viscous liquid

Originator

Bepanthene,Roche,France,1951

The Uses of Dexpanthenol

Dexpanthenol may be used as an analytical reference standard for the determination of the analyte in pharmaceutical formulations by various chromatography techniques as well as partial least-squares multivariate calibration.

The Uses of Dexpanthenol

cholinergic

The Uses of Dexpanthenol

D-Panthenol is an analogue of pantothenic acid (P190300), a member of the B complex vitamins. D-Panthenol is the biologically active enantiomer of Panthenol.

The Uses of Dexpanthenol

immunosuppressant, mitoxantrone analogue less toxic on cardiac tissue antineoplastic

Indications

Injection: Prophylactic use immediately after major abdominal surgery to minimize the possibility of paralytic ileus. Intestinal atony causing abdominal distention; postoperative or postpartum retention of flatus, or postoperative delay in resumption of intestinal motility; paralytic ileus.
Topical: This medication is used as a moisturizer to treat or prevent dry, rough, scaly, itchy skin and minor skin irritations (e.g., diaper rash, skin burns from radiation therapy).

What are the applications of Application

D-Panthenol is a provitamin of B5

Background

Dexpanthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Dexpanthenol is enzymatically cleaved to form pantothenic acid, which is an essential component of Coenzyme A, which acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium.
Due to its good penetration and high local concentrations, dexpanthanol is used in many topical products, such as ointments and lotions for treatment of dermatological conditions to relieve itching or promote healing. Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties .
Dexpanthenol is also available as a racemic mixture containing both the dextrorotatory form (dexpanthenol) and the levorotatory form (levopanthenol) as Panthenol. While pantothenic acid is optically active, only the dextrorotatory form (dexpanthenol) is biologically active.

definition

ChEBI: Pantothenol is a monocarboxylic acid amide that is 3,3-dimethylbutanamide substituted by hydroxy groups at positions 2 and 4 and a 3-hydroxypropyl group at the carbomyl nitrogen. It has a role as a cholinergic drug and a provitamin. It is an amino alcohol and a monocarboxylic acid amide.

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.

brand name

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

Therapeutic Function

Gastrointestinal drug

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.

Flammability and Explosibility

Non flammable

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.

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.

Pharmacokinetics

Pantothenic acid is a precursor of coenzyme A, which serves as a cofactor for a variety of enzyme-catalyzed reactions involving transfer of acetyl groups. The final step in the synthesis of acetylcholine consists of the choline acetylase transfer of acetyl group from acetylcoenzyme A to choline. Acetylcholine is the neurohumoral transmitter in the parasympathetic system and as such maintains the normal functions of the intestine. Decrease in acetylcholine content would result in decreased peristalsis and in extreme cases adynamic ileus.

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.

Metabolism

Dexpanthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A.

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.]