tamibarotene   Click here for help

GtoPdb Ligand ID: 2648

Synonyms: AM-80 | AM80 | Amnolake® | retinobenzoic acid
Approved drug PDB Ligand
tamibarotene is an approved drug
Compound class: Synthetic organic
Comment: This compound is a retinoic acid receptor α (RARα) agonist [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 66.4
Molecular weight 351.18
XLogP 5.9
No. Lipinski's rules broken 1
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Canonical SMILES O=C(c1ccc(cc1)C(=O)O)Nc1ccc2c(c1)C(C)(C)CCC2(C)C
Isomeric SMILES O=C(c1ccc(cc1)C(=O)O)Nc1ccc2c(c1)C(C)(C)CCC2(C)C
InChI InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
1. Kagechika H, Kawachi E, Hashimoto Y, Himi T, Shudo K. (1988)
Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.
J Med Chem, 31 (11): 2182-92. [PMID:3184125]
2. Nagy L, Thomázy VA, Shipley GL, Fésüs L, Lamph W, Heyman RA, Chandraratna RA, Davies PJ. (1995)
Activation of retinoid X receptors induces apoptosis in HL-60 cell lines.
Mol Cell Biol, 15 (7): 3540-51. [PMID:7791761]
3. Takenaga M, Ohta Y, Tokura Y, Hamaguchi A, Shudo K, Okano H, Igarashi R. (2009)
The effect of Am-80, a synthetic retinoid, on spinal cord injury-induced motor dysfunction in rats.
Biol Pharm Bull, 32 (2): 225-31. [PMID:19182380]
4. Thacher SM, Vasudevan J, Chandraratna RA. (2000)
Therapeutic applications for ligands of retinoid receptors.
Curr Pharm Des, 6 (1): 25-58. [PMID:10637371]
5. Vizirianakis IS, Chatzopoulou M, Bonovolias ID, Nicolaou I, Demopoulos VJ, Tsiftsoglou AS. (2010)
Toward the development of innovative bifunctional agents to induce differentiation and to promote apoptosis in leukemia: clinical candidates and perspectives.
J Med Chem, 53 (19): 6779-810. [PMID:20925433]