Pantolactams as Androgen Receptor Antagonists for the Topical Suppression of Sebum Production

September 2011 in “ Bioorganic & Medicinal Chemistry Letters ”

Karen Elaine Sexton, Stephen Barrett, Katy L. Bridgwood, Matthew Carroll, Danielle Dettling, Daniel K. Du, Stephen A. Fakhoury, Victor Fedij, Lain-Yen Hu, Catherine R. Kostlan, David Pocalyko, N. Raheja, Yvonne E. Smith, Veerabahu Shanmugasundaram, Kimberly Jane Wade

pantolactams androgen receptor antagonists sebum production topical application wax esters Hamster Ear Model (+)-isomer AR antagonists

TLDR Pfizer found that pantolactam-based compounds can reduce sebum (skin oil) production when applied topically.

In 2011, Pfizer Global Research & Development conducted a study to identify potent androgen receptor (AR) antagonists that could suppress sebum production when applied topically. They discovered that pantolactam-based compounds were effective AR antagonists. When tested in the Hamster Ear Model, these compounds reduced wax esters, a major component of sebum, leading to further preclinical work. The study also revealed that all AR antagonist activity was found in the (+)-isomer for the pantolactams. Two compounds, 48 and 50, were chosen for additional preclinical studies due to their effectiveness in reducing sebum production.

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Rational Design of a Topical Androgen Receptor Antagonist for the Suppression of Sebum Production with Properties Suitable for Follicular Delivery

research Rational Design of a Topical Androgen Receptor Antagonist for the Suppression of Sebum Production with Properties Suitable for Follicular Delivery

11 citations, May 2010 in “Journal of Medicinal Chemistry”

A new compound was created in 2010 that can control oil production when applied to the skin, and its effects are completely reversible after two weeks.

research Diphenyl Ethers as Androgen Receptor Antagonists for the Topical Suppression of Sebum Production

7 citations, April 2009 in “Bioorganic & Medicinal Chemistry Letters”

Diphenyl ethers can potentially reduce excess oil production when applied on the skin, helping treat conditions like acne.

4-(Alkylthio)- and 4-(Arylthio)-Benzonitrile Derivatives as Androgen Receptor Antagonists for the Topical Suppression of Sebum Production

research 4-(Alkylthio)- and 4-(Arylthio)-Benzonitrile Derivatives as Androgen Receptor Antagonists for the Topical Suppression of Sebum Production

11 citations, March 2009 in “Bioorganic & Medicinal Chemistry Letters”

Chemicals called 4-(alkylthio)- and 4-(arylthio)-benzonitrile derivatives can potentially reduce oil production on skin, which could help treat conditions like acne and hair loss.

research Rational Design and Synthesis of 4-((1R,2R)-2-Hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile (PF-998425), a Novel, Nonsteroidal Androgen Receptor Antagonist Devoid of Phototoxicity for Dermatological Indications

23 citations, October 2008 in “Journal of medicinal chemistry”

PF-998425 is a new, effective, and non-phototoxic treatment for skin conditions related to androgens.

Preparation of 4-Aryl-2-Trifluoromethylbenzonitrile Derivatives as Androgen Receptor Antagonists for Topical Suppression of Sebum Production

research Preparation of 4-Aryl-2-Trifluoromethylbenzonitrile Derivatives as Androgen Receptor Antagonists for Topical Suppression of Sebum Production

11 citations, October 2007 in “Bioorganic & Medicinal Chemistry Letters”

Scientists made a chemical (compound 4e) that can be applied on skin to reduce oil production, which can help with acne, but it might cause skin sensitivity to light.

(1R,2S)-4-(2-Cyano-Cyclohexyl-Oxy)-2-Trifluoromethyl-Benzonitrile, A Potent Androgen Receptor Antagonist For Stimulating Hair Growth And Reducing Sebum Production

research (1R,2S)-4-(2-Cyano-Cyclohexyl-Oxy)-2-Trifluoromethyl-Benzonitrile, A Potent Androgen Receptor Antagonist For Stimulating Hair Growth And Reducing Sebum Production

14 citations, August 2007 in “Bioorganic & Medicinal Chemistry Letters”

The compound (1R,2S)-4-(2-Cyano-cyclohexyl-oxy)-2-trifluoromethyl-benzonitrile can stimulate hair growth and reduce oil production when applied topically.

Synthesis and Biological Evaluation of Amino-Pyridines as Androgen Receptor Antagonists for Stimulating Hair Growth and Reducing Sebum Production

research Synthesis and Biological Evaluation of Amino-Pyridines as Androgen Receptor Antagonists for Stimulating Hair Growth and Reducing Sebum Production

17 citations, August 2007 in “Bioorganic & Medicinal Chemistry Letters”

A compound made by Pfizer can potentially stimulate hair growth and reduce oil production, making it a good candidate for topical use.

research Importance of Sebaceous Glands in Cutaneous Penetration of an Antiandrogen: Target Effect of Liposomes

62 citations, May 1997 in “Journal of Pharmaceutical Sciences”

Sebaceous glands in the skin play a key role in absorbing the antiandrogen drug RU 58841, especially when it's encapsulated in liposomes.

research Treatment of Androgenic Disorders in Women: Acne, Hirsutism, and Alopecia

19 citations, July 1990 in “Cleveland Clinic journal of medicine”

Androgen excess disorders in women were effectively treated with spironolactone, estrogen, and dexamethasone.