temarotene
{{Chembox
| Name = Temarotene
| ImageFile = Temarotene.svg
| ImageSize =
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| IUPACName = 1,1,4,4-tetramethyl-6-[(E)-1-phenylprop-1-en-2-yl]-2,3-dihydronaphthalene
| OtherNames = Ro 15-0788{{cite book |last1=Wolverton |first1=Stephen E. |title=Comprehensive Dermatologic Drug Therapy |date=2001 |publisher=Saunders |isbn=978-0-7216-7728-6 |page=302 |url=https://books.google.com/books?id=LDBtAAAAMAAJ&q=Temarotene |access-date=13 April 2025 |language=en}}
| Section1 = {{Chembox Identifiers
| CASNo = 75078-91-0
| CASNo_Ref = {{Cascite|changed|CAS}}
| ChemSpiderID = 4940787
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| ChEMBL = 554474
| UNII = A28G39IJ7K
| PubChem = 6436116
| InChI = InChI=1S/C23H28/c1-17(15-18-9-7-6-8-10-18)19-11-12-20-21(16-19)23(4,5)14-13-22(20,2)3/h6-12,15-16H,13-14H2,1-5H3/b17-15+
| InChIKey = MUJQTAMVZYFLCR-BMRADRMJSA-N
| SMILES = CC(=CC1=CC=CC=C1)C2=CC3=C(C=C2)C(CCC3(C)C)(C)C
}}
| Section2 = {{Chembox Properties
| H=28|C=23
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| Appearance = Solid powder
| Density = 0.963 g/cm3
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| Section3 = {{Chembox Hazards
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Temarotene is a synthetic arotinoid compound with the molecular formula {{chem2|C23H28}}.{{cite book |last1=Hong |first1=Waun Ki |last2=Lotan |first2=Reuben |title=Retinoids in Oncology |date=24 July 2020 |publisher=CRC Press |isbn=978-1-000-14822-0 |page=92 |url=https://books.google.com/books?id=NijxDwAAQBAJ&dq=Temarotene&pg=PA91 |access-date=13 April 2025 |language=en}}{{cite web |title=NCATS Inxight Drugs — TEMAROTENE |url=https://drugs.ncats.io/drug/A28G39IJ7K |publisher=drugs.ncats.io |access-date=13 April 2025 |language=en}} The compound is an orally active drug known for its immunosuppressive and immunostimulatory activities. Temarotene was also studied as a chemopreventive agent.
Synthesis
Synthesis of arotinoid acid and temarotene starts with mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as a precursor.{{cite journal |last1=Guerrero |first1=Palimécio G. |last2=de Oliveira |first2=Paulo R. |last3=Baroni |first3=Adriano C. M. |last4=Marques |first4=Francisco A. |last5=Labes |first5=Ricardo |last6=Hurtado |first6=Gabriela R. |last7=Dabdoub |first7=Miguel J. |title=Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor |journal=Tetrahedron Letters |date=26 September 2012 |volume=53 |issue=39 |pages=5302–5305 |doi=10.1016/j.tetlet.2012.07.092 |issn=0040-4039|doi-access=free |hdl=11449/194747 |hdl-access=free }}
Uses
Temarotene functions as an orally administered immunomodulator, exhibiting both immunosuppressive and immunostimulatory properties. Studies demonstrate its ability to regulate ornithine decarboxylase (ODC) gene expression in vitro, a mechanism linked to its effects on cellular differentiation and immune response. Temarotene is also used in the study of lichen planus.{{cite web |title=Temarotene {{!}} TargetMol |url=https://www.targetmol.com/compound/temarotene |publisher=targetmol.com |access-date=13 April 2025 |language=en}}