methylnaltrexone   Click here for help

GtoPdb Ligand ID: 7563

Abbreviated name: MNTX
Synonyms: MRZ-2663BR | Relistor®
Approved drug
methylnaltrexone is an approved drug (EMA & FDA (2008))
Compound class: Synthetic organic
Comment: The charged tetravalent nitrogen atom in this molecule reduces its ability to cross the blood-brain barrier, thereby restricting its activity to peripheral targets. This type of peripherally acting mu-opioid receptor antagonist is known by the acronym PAMORA.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 66.76
Molecular weight 356.19
XLogP 0.24
No. Lipinski's rules broken 0
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Canonical SMILES O=C1CCC2(C34C1Oc1c4c(CC2[N+](CC3)(C)CC2CC2)ccc1O)O
Isomeric SMILES O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2[N+](CC3)(C)CC2CC2)ccc1O)O
InChI InChI=1S/C21H25NO4/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13/h4-5,12,16,19,25H,2-3,6-11H2,1H3/p+1/t16-,19+,20+,21-,22?/m1/s1
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Summary of Clinical Use Click here for help
Used to treat the constipation caused by opioid analgesics, when the response to other laxatives has been insufficient. This is principally used for terminal patients receiving high dose pain relief, but may also be used in other patient groups [1].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Acts as an antagonist at μ opioid receptors in the gut, blocking the activity of other opioid drugs in the gut without affecting their analgesic activity in the brain. This helps to reduce opioid-induced constipation.
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