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Tretinoin

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Tretinoin
Clinical data
Trade namesAvita, Renova, Retin-a
AHFS/Drugs.comMonograph
MedlinePlusa682437
License data
Pregnancy
category
  • C(topical), D(oral)(US), X(oral)(Aus)
Routes of
administration		Topical, oral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only
Pharmacokinetic data
Protein binding> 95%
Elimination half-life0.5-2 hours
Identifiers
  • retinoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.573 Edit this at Wikidata
Chemical and physical data
FormulaC20H28O2
Molar mass300.4412 g/mol g·mol−1
3D model (JSmol)
Melting point180 °C (356 °F)
  • O=C(O)\C=C(\C=C\C=C(\C=C\C1=C(\CCCC1(C)C)C)C)C
  • 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 is the acid form of vitamin A and is also known as all-trans retinoic acid or ATRA. It is a drug commonly used to treat acne vulgaris and keratosis pilaris. It is available as a cream or gel (brand names Aberela, Airol, Renova, Atralin, Retin-A, Avita, Retacnyl, Refissa, or Stieva-A). It is also used to treat acute promyelocytic leukemia (APL), and is sold for this indication by Roche under the brand name Vesanoid. It is also available as a generic.

Uses

Dermatology

Tretinoin is most commonly used as a form of acne treatment.[2] It was the first retinoid developed for this type of topical use.[citation needed] Tretinoin is the best studied retinoid in the treatment of photoaging.[3] It is used by some as a hair loss treatment and also a component of many commercial products that are advertised as being able to slow skin aging or remove wrinkles.[citation needed] Topical tretinoin is also used to treat and reduce the appearance of stretch marks by increasing collagen production in the dermis.[4]

Leukemia

Tretinoin, marketed as Vesanoid, is used to treat at least one form of cancer (acute promyelocytic leukemia (APL), also called acute myeloid leukemia subtype M3), usually together with other drugs, by causing the immature blood cells to differentiate (i.e. mature).[5][6] The pathology of the leukemia is due to the highly proliferative immature cells; retinoic acid drives these cells to develop into functional cells, which helps to alleviate the disease.[citation needed] It is usually prescribed for 15 days every three months at about 8–10 10 mg capsules per day.[citation needed]

Clinical pharmacology

Successfully treating acute promyelocytic leukemia (APL) with Tretinoin was a major breakthrough in APL therapy.[7] It works in APL because the majority of cases involve a chromosomal translocation of chromosomes 15 and 17, which causes genetic fusion of the retinoic acid receptor (RAR) gene to the promyelocytic leukemia (PML) gene.[citation needed] This fusion PML-RAR protein is responsible for preventing immature myeloid cells from differentiating into more mature cells. This block in differentiation is thought to cause leukemia. ATRA acts on PML-RAR to lift this block, causing the immature promyelocytes to differentiate to normal mature blood cells thus decreasing promyelocytes.[citation needed]

Side effects

In dermatological use

When used, dryness or increased sensitivity to sunlight of the affected skin may occur.[8] More sensitive patients may also experience redness, scaling, itching, and burning.[9] A gradual increase in the frequency and amount of tretinoin application is best, as this allows one's skin to adequately adjust to the drug. Patients should be careful to follow their physician's recommendations when beginning a round of treatment.

This product increases the risk of sunburn;[10] care should be taken (shade, sunscreen, etc.) to protect treated skin from overexposure to ultraviolet light.

Because usage of tretinoin may cause thinning of the skin, it is strongly recommended that patients who are using the drug abstain from hair removal waxing.[citation needed] The wax will, when removed, pull off the top level of epithelium (skin) with it, leaving a red, inflamed, sore mark for several days.[citation needed] Tweezing or threading (epilation) is a viable option for hair removal. The recommended timeframe to wait for a waxing treatment after using tretinoin varies from source to source; anywhere from five days to three months have been reported. Patients should consult with their aesthetician and dermatologist to discuss the best hair removal options during or after tretinoin use.[citation needed]

In leukemia use

There is a unique complication of retinoic acid syndrome in patients with acute promyelocytic leukemia. This is associated with the development of dyspnea, fever, weight gain, peripheral edema and is treated with dexamethasone. The etiology of retinoic acid syndrome has been attributed to capillary leak syndrome from cytokine release from the differentiating promyelocytes.

Teratogenicity

It is a teratogen, and therefore can cause birth defects and tests have shown increases in fetal skull abnormalities in rats. Women who are or may be pregnant, or who are seeking to become pregnant, are therefore warned against using it.[11] This teratogenic effect is caused by the interference of the exogenous retinoic acid with endogenous retinoic acid signaling, which plays a role in patterning the developing embryo. However the risks of topical tretinoin to the fetus seems to be limited.[12]

Research uses

A study published by the European Respiratory Journal in 2002, suggested that tretinoin can reverse the effects of emphysema in mice by returning elasticity (and regenerating lung tissue through gene mediation) to the alveoli.[13] Studies suggested that this might form a promising treatment in human emphysema patients.[14] However, a newer follow-up study done in 2006 found inconclusive results ("no definitive clinical benefits") using Vitamin A (retinoic acid) in treatment of emphysema in humans and stated that further research is needed to reach conclusions on this treatment.[15]

®123 ==See also==

Manufacture

Lewin, Anita H.; Whaley, M. Glenn; Parker, Steven R.; Carroll, F. Ivy; Moreland, Charles G. (1982). "12-Carboxyretinoic acids. Synthesis and structure". The Journal of Organic Chemistry. 47 (10): 1799–1807. doi:10.1021/jo00349a001. {{cite journal}}: Unknown parameter |month= ignored (help)

Footnotes

  1. ^ "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 Oct 2023.
  2. ^ MedlinePlus Drug Information: Tretinoin Topical
  3. ^ Stefanaki C, Stratigos A, Katsambas A (2005). "Topical retinoids in the treatment of photoaging". J Cosmet Dermatol. 4 (2): 130–4. doi:10.1111/j.1473-2165.2005.40215.x. PMID 17166212. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Arthur W. Perry (2007). Straight talk about cosmetic surgery. Yale University Press. p. 63. ISBN 978-0-300-12104-9.
  5. ^ Huang M, Ye Y, Chen S, Chai J, Lu J, Zhoa L, Gu L, Wang Z (1988). "Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia" (PDF). Blood. 72 (2): 567–72. PMID 3165295.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ Castaigne S, Chomienne C, Daniel M, Ballerini P, Berger R, Fenaux P, Degos L (1990). "All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results" (PDF). Blood. 76 (9): 1704–9. PMID 2224119.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Sanz M (2006). "Treatment of acute promyelocytic leukemia" (PDF). Hematology Am Soc Hematol Educ Program. 2006 (1): 147–55. doi:10.1182/asheducation-2006.1.147. PMID 17124054.
  8. ^ Retin-A (Tretinoin)
  9. ^ Tretinoin Side Effects | Drugs.com
  10. ^ How to Use Tretinoin (Retin-A)
  11. ^ Tretinoin facts and comparisons at Drugs.com
  12. ^ Loureiro KD, Kao KK, Jones KL, Alvarado S, Chavez C, Dick L, Felix R, Johnson D, Chambers CD (2005). "Minor malformations characteristic of the retinoic acid embryopathy and other birth outcomes in children of women exposed to topical tretinoin during early pregnancy". Am J Med Genet A. 136 (2): 117–21. doi:10.1002/ajmg.a.30744. PMID 15940677. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  13. ^ "Vitamin may cure smoking disease". BBC News Online. December 22, 2003. Retrieved 2006-11-18.
  14. ^ Mao J, Goldin J, Dermand J, Ibrahim G, Brown M, Emerick A, McNitt-Gray M, Gjertson D, Estrada F, Tashkin D, Roth M (1 March 2002). "A pilot study of all-trans-retinoic acid for the treatment of human emphysema" (PDF). Am J Respir Crit Care Med. 165 (5): 718–23. PMID 11874821.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  15. ^ Roth M, Connett J, D'Armiento J, Foronjy R, Friedman P, Goldin J, Louis T, Mao J, Muindi J, O'Connor G, Ramsdell J, Ries A, Scharf S, Schluger N, Sciurba F, Skeans M, Walter R, Wendt C, Wise R (2006). "Feasibility of retinoids for the treatment of emphysema study" (PDF). Chest. 130 (5): 1334–45. doi:10.1378/chest.130.5.1334. PMID 17099008.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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