naldemedine   Click here for help

GtoPdb Ligand ID: 9150

Synonyms: compound 9k [PMID: 30446313] | S-297,995 | S-297995
Approved drug
naldemedine is an approved drug (FDA (2017), EMA (2019))
Compound class: Synthetic organic
Comment: Naldemedine (S-297995) is a dual μ/δ opioid receptor antagonist, designed to act peripherally (peripherally acting mu-opioid receptor antagonist or PAMORA) [1]. It is used clinically for its ability to counteract opioid agonist-induced adverse effects such as constipation, nausea, and vomiting. Naldemedine was developed by Shionogi Inc. It is the compound claimed in patent WO2013172297 with formula IA (17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3,6,14-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]morphinan-7-carboxamide 4-methylbenzenesulfonic acid) [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 141.18
Molecular weight 570.25
XLogP 3.31
No. Lipinski's rules broken 0
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Canonical SMILES O=C(C1=C(O)C2C34C(C1)(O)C(Cc1c4c(O2)c(O)cc1)N(CC3)CC1CC1)NC(c1onc(n1)c1ccccc1)(C)C
Isomeric SMILES O=C(C1=C(O)[C@H]2[C@]34[C@](C1)(O)[C@@H](Cc1c4c(O2)c(O)cc1)N(CC3)CC1CC1)NC(c1onc(n1)c1ccccc1)(C)C
InChI InChI=1S/C32H34N4O6/c1-30(2,29-33-27(35-42-29)18-6-4-3-5-7-18)34-28(39)20-15-32(40)22-14-19-10-11-21(37)25-23(19)31(32,26(41-25)24(20)38)12-13-36(22)16-17-8-9-17/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39)/t22-,26+,31+,32-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2017), EMA (2019))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9484 naldemedine
Synonyms Click here for help
compound 9k [PMID: 30446313] | S-297,995 | S-297995
Database Links Click here for help
Specialist databases
GPCRdb Ligand naldemedine
Other databases
ChEMBL Ligand CHEMBL2105755
DrugCentral Ligand 5220
GtoPdb PubChem SID 315661235
PubChem CID 54732242
Search Google for chemical match using the InChIKey AXQACEQYCPKDMV-RZAWKFBISA-N
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UniChem Compound Search for chemical match using the InChIKey AXQACEQYCPKDMV-RZAWKFBISA-N
UniChem Connectivity Search for chemical match using the InChIKey AXQACEQYCPKDMV-RZAWKFBISA-N
Wikipedia Naldemedine