isotretinoin   

GtoPdb Ligand ID: 7600

Synonyms: 13-cis retinoic acid
isotretinoin is an approved drug (FDA (1982))
Compound class: Synthetic organic
Comment: Isotretinoin is a retinoid type drug ie it is a vitamin A-like molecule. It is the endogenous agonist for retinoic acid receptors (RARs).
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2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
Canonical SMILES CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
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-
InChI Key SHGAZHPCJJPHSC-XFYACQKRSA-N
No information available.
Summary of Clinical Use
Primarily used to treat cystic acne.
Mechanism Of Action and Pharmacodynamic Effects
Isotretinoin has a low affinity for retinoic acid receptors (RAR) and retinoid X receptors (RXR), but metabolites may act as agonists of these nuclear receptors [1]. Activation of RAR modulates the expression of genes essential for regulating cell proliferation and differentiation. Isotretinoin may also posess immunomodulatory and anti-inflammatory activities and has been demonstrated to inhibit ornithine decarboxylase, an action likely to decrease polyamine synthesis and keratinization.
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