alitretinoin   Click here for help

GtoPdb Ligand ID: 2645

Synonyms: 9-cis-retinoic acid | Panretin® | Toctino®
Approved drug PDB Ligand
alitretinoin is an approved drug (FDA (1999), EMA (2000))
Comment: Alitretinoin is an important regulator of gene expression during normal growth and development, as well as in neoplasms. Alitretinoin is a retinoid receptor agonist.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: alitretinoin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
No. Lipinski's rules broken 1
Click here for help
Isomeric SMILES C/C(=C/C=C/C(=C/C(=O)O)/C)/C=C/C1=C(C)CCCC1(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+
No information available.
Summary of Clinical Use Click here for help
Used to treat severe chronic hand eczema refractory to potent topical corticosteroids. It can also be used to treat Kaposi sarcoma.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Alitretinoin binds and activates all known intracellular retinoid receptor subtypes. Activated retinoic acid receptors act as transcription factors regulating genes that control cellular differentiation and proliferation in normal and neoplastic cells.