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  Science of Retinoids  
 

Topical retinoids are the most important active ingredient in dermatology today.

Retinoids are Vitamin A derivatives. Tretinoin is the prescription strength of topical Vitamin A while Retinol does not require a prescription. Retinoids are vital to the normal functioning of all skin structures (i.e. skin, hair, eyes, teeth and nails). In the plant kingdom, Vitamin A functions as a free radical scavenger, protecting plants from UV radiation damage. For humans, topical retinoids work as an antioxidant, enhancing normal functioning of the skin and also assisting in repairing DNA from photodamage.

The Retinoid Family .

Vitamin A Metabolites
Retinyl palmitate
      (R = CH2OOCC15H31)
Retinyl proprianate
      (R = CH2OOCC2H5)
Retinyl acetate
      (R = CH2OOCC2H5)

Vitamin A Esters
Retinol
       (R = CH2OH)
RetinolRetinaldehyde
       (R = CHO)
Retinoic Acid
      (R = COOOH)

Retinoids are also known to be humectants that aid in skin hydration. Continuous use of topical retinoids seems to have a cumulative effect in reducing as well as preventing photodamage in skin. Retinoids have also been shown to rebuild the collagen infrastructure in skin.

The basic chemical structure of the retinoid family. Substitute R in the table for the corresponding retinoid chemical value.

 

 

 

 

Retinyl Esters represent the most stable compounds, but are much less effective than its retinol counterparts. Much of the efficacy is lost through the hydrolysis conversion.

When retinol is applied to the skin, it gains entrance to the cells through different receptors. Once inside the cell, most of the retinol is stored in the retinyl ester form. When needed, the retinyl esters are hydrolysized back into retinol.

Once back into the retinol form, the retinol is oxidized into retinaldehyde in a enzymatic process. Retinaldeyhyde by iteself has little biological effect.

The final step is the oxidation of retinaldehyde into retinoic acid, the most potent form of all vitamin A derivatives.

 

 

References

Kligman AM. Topical treatments for photoaged skin – Seperating the reality from the hype. Postgraduate Medicine. August 1997; 102:2. Available at http://www.postgradmed.com/issues/1997/08_97/kligman.shtml. Accessed June 9, 2008.

Terezakis, NK, Resnik, BS, Bazzano, GS. A slow release vehicle with good bioavailablity to minimize the irritancy of tretinoin. American Academy of Dermatology Annual Meeting Poster Abstract. Available at Advanced Skin Technology.

Kligman LH, Gans, EH. Re-emergence of topical retinol in dermatology. Journal of Dermatological Treatment. 200:11,47-52

Draelos, ZD. Cosmetic consultation: what’s in a formulation? Cosmetic Dermatology. November 2003; 16: 11, 56-58.

Pierard-Franchimont C, Pierard GE, Henry F, Vroome V, Cauwenbergh G. A randomized, placebo-controlled trial of topical retinol in the treatment of cellulite. American Journal of Clinical Dermatology. Nov-Dec 2000; 1(6):369-74.

Antille C, Tran C, Sorg O, et al. Vitamin A exerts a photoprotective action in skin by absorbing ultraviolet B radiation. Journal of Investigative Dermatology. November 2003;121,1163-1167.

Duell EA, Kang S, Voorhees J. Unoccluded retinol penetrates human skin in vivo more effectively than unoccluded retinyl palmitate or retinoic acid. Journal of Investigative Dermatology. September 1997;109(3):301-5.

Kockaert M, Neumann M. Systemic and topical drugs for aging skin. Journal of Drugs in Dermatology. August 2003;2(4):435-41.

Elder J, Kang S, Voorhees J, et al. Retinoid induction of CRABP II mRNA in human dermal fibroblasts. Journal of Investigative Dermatology. March 1996;106:517

Varani J, et al. Vitamin A antagonizes decreased cell growth and elevated collagen-degrading matrix metalloproteinases and stimulates collagen accumulation in naturally aged human skin. Journal of Investigative Dermatology. March 2000;114:480-86.

Kang S, Fisher G, Voorhees, et al. Application of retinol to human skin in vivo induces epidermal hyperplasia and cellular retinoid binding proteins characteristic of retinoic acid but without measurable retinoic acid levels of irritation. Journal of Investigative Dermatology. July1995; 105(1):80-6.

Kafi R, Kwak HR, Schumacher WE, et al. Improvement of naturally aged skin with vitamin A (retinol) Archives of Dermatology. 2007;143(5):606-612.

Detrie, C., et al. A Supplement to Cosmetic Dermatology - Revisting Retinol. January 2005, 18: 1 S1, 1-20

 
 
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