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
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
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 |
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Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16885013 |
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Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16885013 |
PubMed
Title | Date | PubMed |
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Anticonvulsant preclinical profile of CHF 3381: dopaminergic and glutamatergic mechanisms. | 2001 Sep |
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Neuroprotective activity of CHF3381, a putative N-methyl-D-aspartate receptor antagonist. | 2002 Nov 15 |
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Safety, pharmacokinetics, and pharmacodynamics of CHF 3381, a novel N-methyl-D-aspartate antagonist, after single oral doses in healthy subjects. | 2003 Aug |
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Mechanisms of action of CHF3381 in the forebrain. | 2003 Aug |
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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 |
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CHF 3381. | 2004 |
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Steady-state pharmacokinetics and pharmacodynamics of CHF3381, a novel antineuropathic pain agent, in healthy subjects. | 2005 Apr |
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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 |
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CHF3381, a novel antinociceptive agent, attenuates capsaicin-induced pain in rats. | 2005 Sep 20 |
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CHF3381, a N-methyl-D-aspartate receptor antagonist and monoamine oxidase-A inhibitor, attenuates secondary hyperalgesia in a human pain model. | 2006 Aug |
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The antinociceptive effect of systemic gabapentin is related to the type of sensitization-induced hyperalgesia. | 2007 Jun 5 |
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Indantadol, a novel NMDA antagonist and nonselective MAO inhibitor for the potential treatment of neuropathic pain. | 2007 Sep |
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Pharmacodynamics of memantine: an update. | 2008 Mar |
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Differential effects of locally and systemically administered soluble glycoprotein 130 on pain and inflammation in experimental arthritis. | 2010 |
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
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DBSALT002409
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202914-18-9
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ACTIVE MOIETY
SUBSTANCE RECORD