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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
InChI Key JVLBPIPGETUEET-GAAHOAFPSA-O
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2008))
IUPAC Name Click here for help
(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one
International Nonproprietary Names Click here for help
INN number INN
8728 methylnaltrexone bromide
Synonyms Click here for help
MRZ-2663BR | Relistor®
Database Links Click here for help
CAS Registry No. 83387-25-1 (source: Scifinder)
ChEMBL Ligand CHEMBL1186579
DrugBank Ligand DB06800
DrugCentral Ligand 4616
GtoPdb PubChem SID 223365899
PubChem CID 5361918
Search Google for chemical match using the InChIKey JVLBPIPGETUEET-GAAHOAFPSA-O
Search Google for chemicals with the same backbone JVLBPIPGETUEET
Search PubMed clinical trials methylnaltrexone bromide
Search PubMed titles methylnaltrexone bromide
Search PubMed titles/abstracts methylnaltrexone bromide
Search UniChem for chemical match using the InChIKey JVLBPIPGETUEET-GAAHOAFPSA-O
Search UniChem for chemicals with the same backbone JVLBPIPGETUEET
Wikipedia Methylnaltrexone