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Details

Stereochemistry ACHIRAL
Molecular Formula C11H14N2O.ClH
Molecular Weight 226.703
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDANTADOL HYDROCHLORIDE

SMILES

Cl.NC(=O)CNC1CC2=C(C1)C=CC=C2

InChI

InChIKey=JPNNIRXUJSPGRM-UHFFFAOYSA-N
InChI=1S/C11H14N2O.ClH/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);1H

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

Molecular Formula ClH
Molecular Weight 36.461
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
Neuroprotective activity of CHF3381, a putative N-methyl-D-aspartate receptor antagonist.
2002 Nov 15
Mechanisms of action of CHF3381 in the forebrain.
2003 Aug
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 N-methyl-D-aspartate receptor antagonist and monoamine oxidase-A inhibitor, attenuates secondary hyperalgesia in a human pain model.
2006 Aug
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 07:52:31 GMT 2023
Edited
by admin
on Sat Dec 16 07:52:31 GMT 2023
Record UNII
YHA48V735B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDANTADOL HYDROCHLORIDE
Common Name English
CHF-3381
Common Name English
ACETAMIDE, 2-((2,3-DIHYDRO-1H-INDEN-2-YL)AMINO)-, MONOHYDROCHLORIDE
Systematic Name English
ACETAMIDE, 2-((2,3-DIHYDRO-1H-INDEN-2-YL)AMINO)-, HYDROCHLORIDE (1:1)
Systematic Name English
CHF-3381.01
Code English
Code System Code Type Description
EPA CompTox
DTXSID50174169
Created by admin on Sat Dec 16 07:52:31 GMT 2023 , Edited by admin on Sat Dec 16 07:52:31 GMT 2023
PRIMARY
DRUG BANK
DBSALT002409
Created by admin on Sat Dec 16 07:52:31 GMT 2023 , Edited by admin on Sat Dec 16 07:52:31 GMT 2023
PRIMARY
FDA UNII
YHA48V735B
Created by admin on Sat Dec 16 07:52:31 GMT 2023 , Edited by admin on Sat Dec 16 07:52:31 GMT 2023
PRIMARY
PUBCHEM
10198454
Created by admin on Sat Dec 16 07:52:31 GMT 2023 , Edited by admin on Sat Dec 16 07:52:31 GMT 2023
PRIMARY
CAS
202914-18-9
Created by admin on Sat Dec 16 07:52:31 GMT 2023 , Edited by admin on Sat Dec 16 07:52:31 GMT 2023
PRIMARY
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