Structure via PubChem · Public domain (PubChem)
tretinoin
Sign in to saveAlso known as all-trans-retinoic acid (ATRA), Avita®, Renova®, (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid, 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid, beta-Retinoate, trans-Retinoate, 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate
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 is applied to the skin as a cream, gel or ointment. For acute promyelocytic leukemia, it is effective only when the RARA-PML fusion mutation is present and is taken by mouth for up to three months. Topical tretinoin is also the most extensively investigated retinoid therapy for photoaging.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470612798
- Drug.image
- Tretinoin structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 275
- Drug.pronounce
- See pronunciation note
- Drug.tradename
- Retin-A, Avita, Renova, others
- Drug.Drugs.com
- Topical
- Drug.MedlinePlus
- a608032
- Drug.DailyMedID
- Tretinoin
- Drug.pregnancy_AU
- X
- Drug.pregnancy_AU_comment
- / (Oral); D (Topical)
- Drug.routes_of_administration
- Topical, by mouth
- Drug.ATC_prefix
- D10
- Drug.ATC_suffix
- AD01
- Drug.ATC_supplemental
- ,
- Drug.legal_AU
- S4
- Drug.legal_BR
- C2
via Wikipedia infobox
Chemical data
- Formula
- C20H28O2
- Molecular weight
- 300.4 g/mol
- IUPAC name
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
- SMILES
- CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
- InChIKey
- SHGAZHPCJJPHSC-YCNIQYBTSA-N
- XLogP
- 6.3
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
25,185 papers- Comparing Tretinoin to Other Topical Therapies in the Treatment of Skin Photoaging: A Systematic Review.American journal of clinical dermatology · 2024
- Tretinoin Review With Newer Formulations: Providing Effective and Tolerable Solutions in Clinical Practice.Journal of drugs in dermatology : JDD · 2023
- Clindamycin/tretinoin: clindamycin phosphate/tretinoin gel.Drugs in R&D · 2005
- Topical tretinoin research: an historical perspective.The Journal of international medical research · 1990
- Tretinoin loaded NLCs-based sunscreen cream; preparation and characterization.Pakistan journal of pharmaceutical sciences · 2025
via PubMed
Wikidata facts
- Subclass of
- retinoic acid
- Has part
- hydrogen
- Mass
- 300.209
- Has use
- medication
Show 12 more facts
- chemical formula
- C₂₀H₂₈O₂
- World Health Organisation international non-proprietary name
- tretinoin
- melting point
- 181
- medical condition treated
- acne
- canonical SMILES
- CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
- isomeric SMILES
- CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
- Commons category
- Tretinoin
- subject has role
- primary metabolite
- MCN code
- 3004.50.60
- found in taxon
- Homo sapiens
- significant drug interaction
- oxytetracycline
- legal status (medicine)
- boxed warning
Sources (8)
via Wikidata · CC0
~12 min read
Encyclopedic overview
16 sectionsContents
- Medical uses
- Skin use
- Acne
- Photoaging
- Available forms
- Leukemia
- Side effects
- Dermatology
- Acute promyelocytic leukemia
- Mechanism of action
- Synthesis
- History
- Etymology
- Research
- References
- External links
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 is applied to the skin as a cream, gel or ointment. For acute promyelocytic leukemia, it is effective only when the RARA-PML fusion mutation is present and is taken by mouth for up to three months. Topical tretinoin is also the most extensively investigated retinoid therapy for photoaging.
Common side effects when used as a cream are limited to the skin and include skin redness, peeling, and sun sensitivity. 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. Other severe side effects include high white blood cell counts and blood clots. Use during pregnancy is contraindicated due to the risk of birth defects. It is in the retinoid family of medications.
Excerpted from Wikipedia’s “tretinoin” article, available under the CC BY-SA 4.0 licence.