naltrexone   Click here for help

GtoPdb Ligand ID: 1639

Synonyms: (-)naltrexone | naltrexone HCl | ReVia®
Approved drug
naltrexone is an approved drug (FDA (1998), UK (2011))
Compound class: Synthetic organic
Comment: This is the active isomer of naltrexone. The (+) isomer is inactive at the opioid receptors.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: naltrexone

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 70
Molecular weight 341.16
XLogP 0.43
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C1CCC2(C34C1Oc1c4c(CC2N(CC3)CC2CC2)ccc1O)O
Isomeric SMILES O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O
InChI InChI=1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1
InChI Key DQCKKXVULJGBQN-XFWGSAIBSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1998), UK (2011))
IUPAC Name Click here for help
(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
International Nonproprietary Names Click here for help
INN number INN
3368 naltrexone
Synonyms Click here for help
(-)naltrexone | naltrexone HCl | ReVia®
Database Links Click here for help
Specialist databases
GPCRdb Ligand naltrexone
Other databases
CAS Registry No. 16590-41-3 (source: Scifinder)
ChEBI CHEBI:7465
ChEMBL Ligand CHEMBL19019
DrugBank Ligand DB00704
DrugCentral Ligand 1765
GtoPdb PubChem SID 135650687
PubChem CID 5360515
Search Google for chemical match using the InChIKey DQCKKXVULJGBQN-XFWGSAIBSA-N
Search Google for chemicals with the same backbone DQCKKXVULJGBQN
Search PubMed clinical trials naltrexone
Search PubMed titles naltrexone
Search PubMed titles/abstracts naltrexone
UniChem Compound Search for chemical match using the InChIKey DQCKKXVULJGBQN-XFWGSAIBSA-N
UniChem Connectivity Search for chemical match using the InChIKey DQCKKXVULJGBQN-XFWGSAIBSA-N
Wikipedia Naltrexone