palovarotene   Click here for help

GtoPdb Ligand ID: 8276

Synonyms: CLM-001 | IPN-60120 | IPN60120 | R-667 | R667 | RG-667 | Ro-3300074 | Sohonos®
Approved drug
palovarotene is an approved drug (Canada (2022), FDA (2023))
Compound class: Synthetic organic
Comment: Palovarotene is an orally bioavailable, retinoic acid receptor gamma (RAR-γ) agonist. This compound was originally investegated for its potential to repair alveolar damage in emphysema and COPD [1,8], but it failed to demonstrate significant clinical efficacy. Ipsen acquired palovarotene when it purchased Clementia Pharmaceuticals in 2019, and they repurposed palovarotene for potential to reduce heterotopic ossification in patients with fibrodysplasia ossificans progressiva (FOP) [6,9].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 55.12
Molecular weight 414.23
XLogP 7.85
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)c1ccc(cc1)C=Cc1cc2c(cc1Cn1cccn1)C(C)(C)CCC2(C)C
Isomeric SMILES OC(=O)c1ccc(cc1)/C=C/c1cc2c(cc1Cn1cccn1)C(C)(C)CCC2(C)C
InChI InChI=1S/C27H30N2O2/c1-26(2)12-13-27(3,4)24-17-22(18-29-15-5-14-28-29)21(16-23(24)26)11-8-19-6-9-20(10-7-19)25(30)31/h5-11,14-17H,12-13,18H2,1-4H3,(H,30,31)/b11-8+
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Canada (2022), FDA (2023))
IUPAC Name Click here for help
4-[(E)-2-[5,5,8,8-tetramethyl-3-(pyrazol-1-ylmethyl)-6,7-dihydronaphthalen-2-yl]ethenyl]benzoic acid
International Nonproprietary Names Click here for help
INN number INN
9025 palovarotene
Synonyms Click here for help
CLM-001 | IPN-60120 | IPN60120 | R-667 | R667 | RG-667 | Ro-3300074 | Sohonos®
Database Links Click here for help
ChEMBL Ligand CHEMBL2105648
DrugBank Ligand DB12320
GtoPdb PubChem SID 252166488
PubChem CID 10295295
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UniChem Compound Search for chemical match using the InChIKey YTFHCXIPDIHOIA-DHZHZOJOSA-N
UniChem Connectivity Search for chemical match using the InChIKey YTFHCXIPDIHOIA-DHZHZOJOSA-N