Tretinoin

For the isomer of tretinoin used primarily to treat more severe acne, see Isotretinoin. For all-trans-retinoic acid as the metabolite of vitamin A, see Retinoic acid.

Tretinoin
Clinical data
PronunciationSee pronunciation note
Trade namesRetin-A, Avita, Renova, others
Other namesATRA
AHFS/Drugs.comMonograph
Topical Monograph
MedlinePlusa608032
License data
Pregnancy
category
  • AU: X (High risk)/ (Oral); D (Topical)[1][2]
Routes of
administration		Topical, by mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C2 (Retinoids)[3]
  • UK: POM (Prescription only)
  • US: ℞-only[4][5]
  • EU: Rx-only[6]
Pharmacokinetic data
Protein binding> 95%
Elimination half-life0.5–2 hours
Identifiers
IUPAC name
  • (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.573
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
Melting point180 °C (356 °F)
SMILES
  • CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
InChI
  • InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+ Y
  • Key:SHGAZHPCJJPHSC-YCNIQYBTSA-N dd><htt//60967409 Y Arsen Ramirez Cruzﺁ
  (verify)

Tretinoin, also known as all-trans retinoic acid (ATRA), is a medication used for the treatment of acne and acute promyelocytic leukemia.[7][8][9] For acne, it is applied to the skin as a cream, gel or ointment.[9] For acute promyelocytic leukemia, it is effective only when the RARA-PML fusion mutation is present[10] and is taken by mouth for up to three months.[7] Topical tretinoin is also the most extensively investigated retinoid therapy for photoaging.[11]

Common side effects when used as a cream are limited to the skin and include skin redness, peeling, and sun sensitivity.[9] When taken by mouth, side effects include hypertriglyceridemia, hypercholesterolemia, shortness of breath, headache, numbness, depression, skin dryness, itchiness, hair loss, vomiting, muscle pains, and vision changes.[7] Other severe side effects include high white blood cell counts and blood clots.[7] Use during pregnancy is contraindicated due to the risk of birth defects.[7][1] It is in the retinoid family of medications.[8]

Tretinoin was patented in 1957 and approved for medical use in 1962.[12] It is on the World Health Organization's List of Essential Medicines.[13] Tretinoin is available as a generic medication.[14] In 2022, it was the 238th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[15][16]

  1. ^ a b "Tretinoin (Vesanoid) Use During Pregnancy". Drugs.com. 25 July 2019. Retrieved 16 January 2020.
  2. ^ "Tretinoin topical Use During Pregnancy". Drugs.com. 1 July 2019. Retrieved 16 January 2020.
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  4. ^ Cite error: The named reference OralLabel was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference TopicalLabel was invoked but never defined (see the help page).
  6. ^ "List of nationally authorised medicinal products:Active substance(s): tretinoin (oral formulations)" (PDF). ema.europa.eu. European Medicines Agency. 1 December 2022. Archived (PDF) from the original on 30 January 2023.
  7. ^ a b c d e "Tretinoin". The American Society of Health-System Pharmacists. Archived from the original on 30 November 2016. Retrieved 8 December 2016.
  8. ^ a b Tivnan A (2016). Resistance to Targeted Therapies Against Adult Brain Cancers. Springer. p. 123. ISBN 978-3-319-46505-0. Archived from the original on 5 November 2017.
  9. ^ a b c British national formulary: BNF 69 (69 ed.). British Medical Association. 2015. pp. 627, 821–822. ISBN 978-0-85711-156-2.
  10. ^ Yoshida H, Kitamura K, Tanaka K, Omura S, Miyazaki T, Hachiya T, et al. (July 1996). "Accelerated degradation of PML-retinoic acid receptor alpha (PML-RARA) oncoprotein by all-trans-retinoic acid in acute promyelocytic leukemia: possible role of the proteasome pathway". Cancer Research. 56 (13): 2945–2948. PMID 8674046.
  11. ^ "Retinoids, topical". American Osteopathic College of Dermatology.
  12. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 476. ISBN 978-3-527-60749-5. Archived from the original on 5 November 2017.
  13. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  14. ^ "Tretinoin topical". The American Society of Health-System Pharmacists. Archived from the original on 16 May 2016. Retrieved 8 December 2016.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Tretinoin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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