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Tretinoin information


Tretinoin
Clinical data
PronunciationSee pronunciation note
Trade namesRetin-a, Avita, Renova, others
Other namesATRA
AHFS/Drugs.comMonograph
Topical Monograph
MedlinePlusa608032
License data
  • US DailyMed: Tretinoin
Pregnancy
category
  • AU: X (High risk)/ (Oral); D (Topical)[1][2]
Routes of
administration
Topical, by mouth
ATC code
  • D10AD01 (WHO) L01XF01 (WHO), D10AD51 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C2 (Retinoids)[4]
  • UK: POM (Prescription only)
  • US: WARNING[3]Rx-only[5][6]
  • EU: Rx-only[7]
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
  • 302-79-4 checkY
PubChem CID
  • 444795
IUPHAR/BPS
  • 2644
DrugBank
  • DB00755 checkY
ChemSpider
  • 392618 checkY
UNII
  • 5688UTC01R
KEGG
  • D00094 checkY
  • C00777 checkY
ChEBI
  • CHEBI:15367 checkY
ChEMBL
  • ChEMBL38 checkY
CompTox Dashboard (EPA)
  • DTXSID7021239 Edit this at Wikidata
ECHA InfoCard100.005.573 Edit this at Wikidata
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
  • Interactive image
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+ checkY
  • Key:SHGAZHPCJJPHSC-YCNIQYBTSA-N checkY
  (verify)

Tretinoin, also known as all-trans retinoic acid (ATRA), is a medication used for the treatment of acne and acute promyelocytic leukemia.[8][9][10] For acne, it is applied to the skin as a cream, gel or ointment.[10] For leukemia, it is taken by mouth for up to three months.[8] 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.[10] When used by mouth, side effects include shortness of breath, headache, numbness, depression, skin dryness, itchiness, hair loss, vomiting, muscle pains, and vision changes.[8] Other severe side effects include high white blood cell counts and blood clots.[8] Use during pregnancy is contraindicated due to the risk of birth defects.[8][1] It is in the retinoid family of medications.[9]

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 2021, it was the 206th most commonly prescribed medication in the United States, with more than 2 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. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ 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.
  5. ^ Cite error: The named reference OralLabel was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference TopicalLabel was invoked but never defined (see the help page).
  7. ^ "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.
  8. ^ 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.
  9. ^ 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.
  10. ^ a b c British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 627, 821–822. ISBN 978-0-85711-156-2.
  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 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  16. ^ "Tretinoin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Tretinoin

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Tretinoin, also known as all-trans retinoic acid (ATRA), is a medication used for the treatment of acne and acute promyelocytic leukemia. For acne, it...

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Adapalene

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over other retinoids. The adapalene molecule is more stable compared to tretinoin and tazarotene, which leads to less concern for photodegradation. It is...

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Photoaging

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characteristic changes to skin induced by chronic UVA and UVB exposure.: 29  Tretinoin is the best studied retinoid in the treatment of photoaging. The deterioration...

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Bisabolol

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repairing sun-damaged skin, and more recently it has been compounded with tretinoin as a topical treatment for acne. Bisabolol is known to have anti-irritant...

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Mequinol

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mixed with tretinoin, a topical retinoid. A common formulation for this drug is an ethanolic solution of 2% mequinol and 0.01% tretinoin by mass. Dermatologists...

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Retinoic acid syndrome

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specifically associated with all-trans retinoic acid (ATRA) (also known as tretinoin) treatment. Subsequently, so-called RAS was recognized in APML patients...

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ATC code D10

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Mesulfen D10AD01 Tretinoin D10AD02 Retinol D10AD03 Adapalene D10AD04 Isotretinoin D10AD05 Motretinide D10AD06 Trifarotene D10AD51 Tretinoin, combinations...

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Vitamin A

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retinol or retinal. As for the risks of too much RA, the prescription drugs tretinoin (all-trans-retinoic acid) and isotretinoin (13-cis-retinoic acid), used...

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Wrinkle

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suggests that tretinoin decreases cohesiveness of follicular epithelial cells, although the exact mode of action is unknown. Additionally, tretinoin stimulates...

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Stretch marks

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tried including laser treatments, glycolic acid, and microdermabrasion. Tretinoin (0.1% w/w), which is a retinoid, has found to be effective on early stretch...

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Isotretinoin

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and is found in small quantities naturally in the body. Its isomer, tretinoin, is also an acne drug. The most common adverse effects are dry lips (cheilitis)...

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Acute promyelocytic leukemia

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by its responsiveness to all-trans retinoic acid (ATRA; also known as tretinoin) therapy. Acute promyelocytic leukemia was first characterized in 1957...

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Tazarotene

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treat acne vulgaris and psoriasis. Like other topical retinoids, such as tretinoin and adapalene, tazarotene can be combined with benzoyl peroxide or an...

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Melasma

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inhibits tyrosinase, an enzyme involved in the production of melanin. Tretinoin, a retinoid, increases skin cell (keratinocyte) turnover. This treatment...

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List of Equinox episodes

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made cancer cells make hemoglobin; Lorraine Baltzer, a research nurse; tretinoin was found to work in 1988, and first prescribed in September 1990; Bruce...

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Azelaic acid

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strength, it’s considered to be as effective as benzoyl peroxide 5%, tretinoin 0.05%, erythromycin 2%, and oral tetracycline at 500 mg-1000 mg. In a...

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Benzoyl peroxide

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retinoid that can be combined with benzoyl peroxide unlike tezarotene and tretinoin. Combination products such as benzoyl peroxide/clindamycin and benzoyl...

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Retinoid

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used topically to help treat skin lesions from Kaposi's sarcoma, and tretinoin (all-trans- retinoic acid) is used to treat acute promyelocytic leukemia...

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Renova

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Minnesota Renova (brand), a Portuguese paper products company Trade name of tretinoin, a treatment for acne and other skin conditions Renova Group, a Russian...

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Pseudofolliculitis barbae

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antibiotics. Tretinoin is a potent treatment that helps even out any scarring after a few months. It is added as a nightly application of tretinoin cream 0...

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Skin whitening

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allowed in cosmetics in Europe, a number of others such as hydroquinone and tretinoin are not. While some countries do not allow mercury compounds in cosmetics...

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Standard for the Uniform Scheduling of Medicines and Poisons

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Isotretinoin Methoxyflurane Pseudoephedrine in large doses Salmeterol Tramadol Tretinoin Trimethoprim All benzodiazepines except flunitrazepam and alprazolam All:...

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Keratosis pilaris

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acid, salicylic acid, vitamin D, fish oil, or topical retinoids such as tretinoin. Improvement of the skin often takes months, and the bumps are likely...

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Acne

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5% benzoyl peroxide gel in the morning and applied a micronized 0.05% tretinoin gel in the evening the overwhelming majority of patients experienced no...

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Acne conglobata

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option to treat with carbon dioxide laser therapy, followed by topical tretinoin therapy has been described. Surgery may be necessary to remove large nodules...

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