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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
Structure of INDANTADOL

SMILES

NC(=O)CNC1CC2=CC=CC=C2C1

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)

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Preclinical evaluation of CHF3381 as a novel antiepileptic agent.
2001 Jun
Safety, pharmacokinetics, and pharmacodynamics of CHF 3381, a novel N-methyl-D-aspartate antagonist, after single oral doses in healthy subjects.
2003 Aug
Mechanisms of action of CHF3381 in the forebrain.
2003 Aug
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 Aug
Steady-state pharmacokinetics and pharmacodynamics of CHF3381, a novel antineuropathic pain agent, in healthy subjects.
2005 Apr
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 May
CHF3381, a novel antinociceptive agent, attenuates capsaicin-induced pain in rats.
2005 Sep 20
CHF3381, a N-methyl-D-aspartate receptor antagonist and monoamine oxidase-A inhibitor, attenuates secondary hyperalgesia in a human pain model.
2006 Aug
The antinociceptive effect of systemic gabapentin is related to the type of sensitization-induced hyperalgesia.
2007 Jun 5
Indantadol, a novel NMDA antagonist and nonselective MAO inhibitor for the potential treatment of neuropathic pain.
2007 Sep
Pharmacodynamics of memantine: an update.
2008 Mar
Differential effects of locally and systemically administered soluble glycoprotein 130 on pain and inflammation in experimental arthritis.
2010
Patents

Sample Use Guides

400 mg twice-daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:06:11 UTC 2023
Edited
by admin
on Sat Dec 16 17:06:11 UTC 2023
Record UNII
Z3867B9SQP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDANTADOL
INN  
INN  
Official Name English
indantadol [INN]
Common Name English
2-((2,3-DIHYDRO-1H-INDEN-2-YL)AMINO)ACETAMIDE
Systematic Name English
V3381
Code English
CHF-3381 FREE BASE
Code English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
Code System Code Type Description
CAS
202844-10-8
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
NCI_THESAURUS
C83796
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
INN
8604
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
MESH
C431890
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
SMS_ID
300000034207
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL3707400
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
FDA UNII
Z3867B9SQP
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
WIKIPEDIA
Indantadol
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID00942416
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
PUBCHEM
10192617
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
DRUG BANK
DB12664
Created by admin on Sat Dec 16 17:06:12 UTC 2023 , Edited by admin on Sat Dec 16 17:06:12 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY