lofentanil   Click here for help

GtoPdb Ligand ID: 13539

Synonyms: R-32792
Compound class: Synthetic organic
Comment: Lofentanil is a potent mu opioid receptor agonist. Structurally it is a fentanyl analogue, with a pharmacological profile similar to that of carfentanil.
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 5
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 49.85
Molecular weight 408.53
XLogP 2.82
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCC(=O)N(C1=CC=CC=C1)[C@@]2(CCN(CCC3=CC=CC=C3)C[C@@H]2C)C(=O)OC
Isomeric SMILES C[C@H]1CN(CC[C@@]1(C(=O)OC)N(C(CC)=O)C2=CC=CC=C2)CCC3=CC=CC=C3
InChI InChI=1S/C25H32N2O3/c1-4-23(28)27(22-13-9-6-10-14-22)25(24(29)30-3)16-18-26(19-20(25)2)17-15-21-11-7-5-8-12-21/h5-14,20H,4,15-19H2,1-3H3/t20-,25+/m0/s1
InChI Key IMYHGORQCPYVBZ-NBGIEHNGSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
methyl (3S,4R)-3-methyl-1-(2-phenylethyl)-4-(N-propanoylanilino)piperidine-4-carboxylate
International Nonproprietary Names Click here for help
INN number INN
4817 lofentanil
Synonyms Click here for help
R-32792
Database Links Click here for help
CAS Registry No. 61380-40-3 (source: WHO INN record)
DrugBank Ligand DB09174
GtoPdb PubChem SID 500839949
PubChem CID 65499
Search Google for chemical match using the InChIKey IMYHGORQCPYVBZ-NBGIEHNGSA-N
Search Google for chemicals with the same backbone IMYHGORQCPYVBZ
Search PubMed clinical trials lofentanil
Search PubMed titles lofentanil
Search PubMed titles/abstracts lofentanil
UniChem Compound Search for chemical match using the InChIKey IMYHGORQCPYVBZ-NBGIEHNGSA-N
UniChem Connectivity Search for chemical match using the InChIKey IMYHGORQCPYVBZ-NBGIEHNGSA-N