samidorphan   Click here for help

GtoPdb Ligand ID: 10651

Synonyms: ALKS-33 | ALKS33 | compound 5 [PMID:15808478] | Lybalvi® (olanzapine + samidorphan)
Approved drug
samidorphan is an approved drug (FDA (2021))
Compound class: Synthetic organic
Comment: Samidorphan (ALKS-33) is a novel μ-opioid receptor antagonist that was developed by Alkermes [1]. Structurally it is a naltrexone analogue. The intention was for samidorphan to be used in combination with the atypical antipsychotic olanzapine (in a formulation known as Lybalvi®, ALKS-3831, or the abbreviation OLZ/SAM) as a therapy for schizophrenia and bipolar disorder. Addition of samidorphan was proposed to mitigate olanzapine-induced weight gain.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 103.86
Molecular weight 370.19
XLogP 0.79
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1CC[C@@]2([C@@]3(C1)CCN([C@@H]2Cc1c3c(O)c(cc1)C(=O)N)CC1CC1)O
Isomeric SMILES O=C1CC[C@@]2([C@@]3(C1)CCN([C@@H]2Cc1c3c(O)c(cc1)C(=O)N)CC1CC1)O
InChI InChI=1S/C21H26N2O4/c22-19(26)15-4-3-13-9-16-21(27)6-5-14(24)10-20(21,17(13)18(15)25)7-8-23(16)11-12-1-2-12/h3-4,12,16,25,27H,1-2,5-11H2,(H2,22,26)/t16-,20-,21-/m1/s1
InChI Key RYIDHLJADOKWFM-MAODMQOUSA-N
References
1. Wentland MP, Lu Q, Lou R, Bu Y, Knapp BI, Bidlack JM. (2005)
Synthesis and opioid receptor binding properties of a highly potent 4-hydroxy analogue of naltrexone.
Bioorg Med Chem Lett, 15 (8): 2107-10. [PMID:15808478]