Temarotene

Temarotene

Names
IUPAC name 1,1,4,4-tetramethyl-6-[(E)-1-phenylprop-1-en-2-yl]-2,3-dihydronaphthalene
Other names Ro 15-0788 [1]
Identifiers
CAS Number	75078-91-0  N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL554474
ChemSpider	4940787
PubChem CID	6436116
UNII	A28G39IJ7K
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+ Key: MUJQTAMVZYFLCR-BMRADRMJSA-N
SMILES CC(=CC1=CC=CC=C1)C2=CC3=C(C=C2)C(CCC3(C)C)(C)C
Properties
Chemical formula	C23H28
Molar mass	304.477 g·mol−1
Appearance	Solid powder
Density	0.963 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Temarotene is a synthetic arotinoid compound with the molecular formula C₂₃H₂₈. ^{[2] [3]} 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. ^[4]

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. ^[5]

References

1. Wolverton, Stephen E. (2001). Comprehensive Dermatologic Drug Therapy. Saunders. p. 302. ISBN   978-0-7216-7728-6 . Retrieved 13 April 2025.
2. Hong, Waun Ki; Lotan, Reuben (24 July 2020). Retinoids in Oncology. CRC Press. p. 92. ISBN   978-1-000-14822-0 . Retrieved 13 April 2025.
3. "NCATS Inxight Drugs — TEMAROTENE". drugs.ncats.io. Retrieved 13 April 2025.
4. Guerrero, Palimécio G.; de Oliveira, Paulo R.; Baroni, Adriano C. M.; Marques, Francisco A.; Labes, Ricardo; Hurtado, Gabriela R.; Dabdoub, Miguel J. (26 September 2012). "Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor". Tetrahedron Letters . 53 (39): 5302–5305. doi: 10.1016/j.tetlet.2012.07.092 . ISSN   0040-4039.
5. "Temarotene | TargetMol". targetmol.com. Retrieved 13 April 2025.