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      Enhancing skin delivery of tranexamic acid via esterification: synthesis and evaluation of alkyl ester derivatives†

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      a , b , c , c , a , a , c , , a ,
      RSC Advances
      The Royal Society of Chemistry

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          Abstract

          Tranexamic acid (TA) is widely used clinically as a skin whitening agent for treating melasma and hyperpigmentation. However, oral administration of TA is often associated with adverse effects. Topical application could mitigate these issues, but the hydrophilic nature of TA limits its topical use. To overcome this limitation, we explored the design of TA alkyl ester prodrugs to enhance skin absorption. Our study specifically focused on the butyl and octyl ester derivatives of TA. The results demonstrated that TA4 and TA8 significantly improved skin penetration and deposition, by approximately 2–3 times compared to unmodified TA. Furthermore, these derivatives were rapidly hydrolyzed to release the parent drug within less than 2 h in both skin homogenates and blood. Safety assessments indicated no significant skin irritation in mice and revealed low cytotoxicity in HaCaT cells when exposed to the TA ester derivatives. We also developed a hydrogel formulation incorporating the TA derivatives, using hydroxyethyl cellulose, propylene glycol, Tween 80, and chlorobutanol. This formulation exhibited good skin absorption, stability, and user experience, making it a promising candidate for topical application. To sum up, the alkyl esterification prodrug design provides a promising approach for enhancing the skin delivery of TA.

          Abstract

          An alkyl esterification prodrug strategy enhances skin penetration and deposition of tranexamic acid.

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          Prodrugs: Challenges and Rewards Part 1

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            Tranexamic Ester and Antipigmentary External Agent with The Same as Active Ingredient

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              Author and article information

              Journal
              RSC Adv
              RSC Adv
              RA
              RSCACL
              RSC Advances
              The Royal Society of Chemistry
              2046-2069
              5 November 2024
              29 October 2024
              5 November 2024
              : 14
              : 47
              : 34996-35004
              Affiliations
              [a ] College of Pharmacy, Shenzhen Technology University Shenzhen 518118 China dingpingtian@ 123456sztu.edu.cn zhangkeda@ 123456sztu.edu.cn
              [b ] Qilu Pharmaceutical Co., Ltd Jinan 250100 China
              [c ] School of Pharmacy, Shenyang Pharmaceutical University Shenyang 110016 China
              Author information
              https://orcid.org/0009-0006-8325-6424
              https://orcid.org/0000-0002-3172-8454
              https://orcid.org/0000-0001-7512-3281
              Article
              d4ra06266c
              10.1039/d4ra06266c
              11537257
              39502868
              dc1b8e31-0e83-4007-9968-b93f4d0489c0
              This journal is © The Royal Society of Chemistry

              This article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

              History
              : 30 August 2024
              : 22 October 2024
              Page count
              Pages: 9
              Funding
              Funded by: Shenzhen Technology University, doi 10.13039/100019839;
              Award ID: 20233108010006
              Award ID: GDRC202305
              Categories
              Chemistry
              Custom metadata
              Paginated Article

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