Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H14N2O |
| Molecular Weight | 190.2417 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)CNC1CC2=C(C1)C=CC=C2
InChI
InChIKey=MNLULKBKWKTZPE-UHFFFAOYSA-N
InChI=1S/C11H14N2O/c12-11(14)7-13-10-5-8-3-1-2-4-9(8)6-10/h1-4,10,13H,5-7H2,(H2,12,14)
| Molecular Formula | C11H14N2O |
| Molecular Weight | 190.2417 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Indantadol (previously known as CHF-3381) is an oral and noncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist and reversible monoamine oxidase-A (MAO-A) inhibitor that is being developed by Vernalis plc, under license from Chiesi Farmaceutici SpA, for the potential treatment of neuropathic pain. In preclinical studies, indantadol exhibited neuroprotective effects after kainate-induced seizures and displayed anticonvulsant and antihyperalgesic activity. Indantadol also caused a dose-dependent decrease in exploratory motility. In a human heat-capsaicin-induced pain model, indantadol at a dose of 500 mg effectively reduced the area of secondary hyperalgesia. The tolerability profile of the drug at single doses up to 600 mg and twice-daily doses up to 400 mg in clinical trials was significantly more favorable than for other NMDA antagonists. Most side effects have been observed to be mild, and include dizziness and asthenia. Indantadol was in phase II clinical trials for the treatment of chronic cough and neuropathic pain. However, these studies had been discontinued.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16885013 |
|||
Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16885013 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential effects of locally and systemically administered soluble glycoprotein 130 on pain and inflammation in experimental arthritis. | 2010 |
|
| Pharmacodynamics of memantine: an update. | 2008-03 |
|
| Indantadol, a novel NMDA antagonist and nonselective MAO inhibitor for the potential treatment of neuropathic pain. | 2007-09 |
|
| The antinociceptive effect of systemic gabapentin is related to the type of sensitization-induced hyperalgesia. | 2007-06-05 |
|
| CHF3381, a N-methyl-D-aspartate receptor antagonist and monoamine oxidase-A inhibitor, attenuates secondary hyperalgesia in a human pain model. | 2006-08 |
|
| CHF3381, a novel antinociceptive agent, attenuates capsaicin-induced pain in rats. | 2005-09-20 |
|
| Mechanistic pharmacokinetic and pharmacodynamic modeling of CHF3381 (2-[(2,3-dihydro-1H-inden-2-yl)amino]acetamide monohydrochloride), a novel N-methyl-D-aspartate antagonist and monoamine oxidase-A inhibitor in healthy subjects. | 2005-05 |
|
| Steady-state pharmacokinetics and pharmacodynamics of CHF3381, a novel antineuropathic pain agent, in healthy subjects. | 2005-04 |
|
| CHF 3381. | 2004 |
|
| Safety, pharmacokinetics, and pharmacodynamics of CHF 3381, a novel N-methyl-D-aspartate antagonist, after single oral doses in healthy subjects. | 2003-08 |
|
| Mechanisms of action of CHF3381 in the forebrain. | 2003-08 |
|
| Antinociceptive activity of the N-methyl-D-aspartate receptor antagonist N-(2-Indanyl)-glycinamide hydrochloride (CHF3381) in experimental models of inflammatory and neuropathic pain. | 2003-08 |
|
| Neuroprotective activity of CHF3381, a putative N-methyl-D-aspartate receptor antagonist. | 2002-11-15 |
|
| Anticonvulsant preclinical profile of CHF 3381: dopaminergic and glutamatergic mechanisms. | 2001-09 |
|
| Preclinical evaluation of CHF3381 as a novel antiepileptic agent. | 2001-06 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17786847
400 mg twice-daily
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 08:44:43 GMT 2025
by
admin
on
Wed Apr 02 08:44:43 GMT 2025
|
| Record UNII |
Z3867B9SQP
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C241
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
202844-10-8
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
C83796
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
8604
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
C431890
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
300000034207
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
CHEMBL3707400
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
Z3867B9SQP
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
Indantadol
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
DTXSID00942416
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
10192617
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY | |||
|
DB12664
Created by
admin on Wed Apr 02 08:44:43 GMT 2025 , Edited by admin on Wed Apr 02 08:44:43 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
TARGET -> INHIBITOR |
|
||
|
TARGET -> INHIBITOR |
|
||
|
|
SALT/SOLVATE -> PARENT |
|
||
|
TARGET -> INHIBITOR |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
|