diphenoxylate   

GtoPdb Ligand ID: 7164

Synonyms: diphenoxylate HCl | Lomotil®
diphenoxylate is an approved drug
Compound class: Synthetic organic
Comment: Diphenoxylate is a phenylpiperidine series, centrally-active opioid antidiarrheal drug. Diphenoxylate is metabolised in vivo to form difenoxin. Both diphenoxylate and difenoxin can be proescribed in fixed-dose combination with atropine to act as an abuse deterrent. Atropine causes severe weakness and nausea if standard doses are exceeded.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 53.33
Molecular weight 452.25
XLogP 6.29
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C#N)c1ccccc1
Isomeric SMILES CCOC(=O)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C#N)c1ccccc1
InChI InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3
InChI Key HYPPXZBJBPSRLK-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name
ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate
International Nonproprietary Names
INN number INN
850 diphenoxylate
Synonyms
diphenoxylate HCl | Lomotil®
Comments
Diphenoxylate is a phenylpiperidine series, centrally-active opioid antidiarrheal drug. Diphenoxylate is metabolised in vivo to form difenoxin. Both diphenoxylate and difenoxin can be proescribed in fixed-dose combination with atropine to act as an abuse deterrent. Atropine causes severe weakness and nausea if standard doses are exceeded.
Database Links
CAS Registry No. 915-30-0
ChEMBL Ligand CHEMBL1201294
DrugBank Ligand DB01081
DrugCentral Ligand 918
GtoPdb PubChem SID 178103739
PubChem CID 13505
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Wikipedia Diphenoxylate