Chemical Properties
clear colorless to slightly yellow viscous liquid
Uses
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.
Uses
immunosuppressant, mitoxantrone analogue less toxic on cardiac tissue antineoplastic
Originator
Bepanthene,Roche,France,1951
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
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.
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.]
