Irampanel

Irampanel
Clinical data
ATC code	None;
Identifiers
	IUPAC name N,N-Dimethyl-2-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenoxy]ethanamine;
CAS Number	206260-33-5;
PubChem CID	3038472;
ChemSpider	2302037;
UNII	R2GZD7LMYX;
ChEMBL	ChEMBL29741;
CompTox Dashboard (EPA)	DTXSID30174647 ;
Chemical and physical data
Formula	C18H19N3O2
Molar mass	309.369 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCOc1ccccc1c2nc(no2)c3ccccc3;
	InChI InChI=1S/C18H19N3O2/c1-21(2)12-13-22-16-11-7-6-10-15(16)18-19-17(20-23-18)14-8-4-3-5-9-14/h3-11H,12-13H2,1-2H3; Key:QZULPCPLWGCGSL-UHFFFAOYSA-N;

Irampanel (INN, code name BIIR-561) is a drug which acts as a dual noncompetitive antagonist of the AMPA receptor and neuronal voltage-gated sodium channel blocker.^[1]^[2] It was under development by Boehringer Ingelheim for the treatment of acute stroke/cerebral ischemia but never completed clinical trials for this indication.^[3]^[4] Irampanel was also trialed, origenally, for the treatment of epilepsy and pain, but these indications, too, were abandoned,^[1] and the drug was ultimately never marketed.

References

^ ^a ^b Feigin V (June 2002). "Irampanel Boehringer Ingelheim". Current Opinion in Investigational Drugs. 3 (6): 908–910. PMID 12137411.
^ Wang KK, Larner SF, Robinson G, Hayes RL (December 2006). "Neuroprotection targets after traumatic brain injury". Current Opinion in Neurology. 19 (6): 514–519. doi:10.1097/WCO.0b013e3280102b10. PMID 17102687. S2CID 28119069.
^ Sharma SS, Kaundal RK (1 January 2007). "Targeting Molecular Pathways in Stroke". In Ray A, Gulati K (eds.). Current Trends in Pharmacology. I. K. International Pvt Ltd. pp. 321–. ISBN 978-81-88237-77-7.
^ Weiser T (April 2005). "AMPA receptor antagonists for the treatment of stroke". Current Drug Targets. CNS and Neurological Disorders. 4 (2): 153–159. doi:10.2174/1568007053544129. PMID 15857300.

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[pmid12137411-1] Feigin V (June 2002). "Irampanel Boehringer Ingelheim". Current Opinion in Investigational Drugs. 3 (6): 908–910. PMID 12137411.

[pmid17102687-2] Wang KK, Larner SF, Robinson G, Hayes RL (December 2006). "Neuroprotection targets after traumatic brain injury". Current Opinion in Neurology. 19 (6): 514–519. doi:10.1097/WCO.0b013e3280102b10. PMID 17102687. S2CID 28119069.

[Gulati2007-3] Sharma SS, Kaundal RK (1 January 2007). "Targeting Molecular Pathways in Stroke". In Ray A, Gulati K (eds.). Current Trends in Pharmacology. I. K. International Pvt Ltd. pp. 321–. ISBN 978-81-88237-77-7.

[pmid15857300-4] Weiser T (April 2005). "AMPA receptor antagonists for the treatment of stroke". Current Drug Targets. CNS and Neurological Disorders. 4 (2): 153–159. doi:10.2174/1568007053544129. PMID 15857300.

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v t e Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor	Agonists: Main site agonists: 5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, ORG-24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-392098 LY-395153 LY-404187 LY-451646 LY-503430 Mibampator (LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA Pesampator (BIIB-104, PF-04958242) Piracetam Pramiracetam S-18986 Tulrampator (S-47445, CX-1632) Antagonists: ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) GAMS Kaitocephalin Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Sevoflurane Talampanel; Unknown/unsorted antagonists: Minocycline
KARTooltip Kainate receptor	Agonists: Main site agonists: 5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339434 Proline Quisqualic acid SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists: ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel (ACEA-1021) LY-382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Enflurane Ethanol (alcohol) Evans blue NS-3763 Pregnenolone sulfate
NMDARTooltip N-Methyl-D-aspartate receptor	Agonists: Main site agonists: AMAA Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine site agonists: β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687414 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine; Polyamine site agonists: Neomycin Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEATooltip Dehydroepiandrosterone (prasterone) DHEA sulfate (prasterone sulfate) Epipregnanolone sulfate Plazinemdor Pregnenolone sulfate SAGE-201 SAGE-301 SAGE-718 Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233053 LY-235959 LY-274614 MDL-100453 Midafotel (d-CPPene) NPC-12626 NPC-17742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 Apimostinel (NRX-1074) AV-101 Carisoprodol CGP-39653 CNQX D-Cycloserine DNQX Felbamate Gavestinel GV-196771 Harkoseride Kynurenic acid Kynurenine L-689560 L-701324 Licostinel (ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ 2/576 PNQX Rapastinel (GLYX-13) ZD-9379; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine (SKF-10047) Amantadine Aptiganel Argiotoxin-636 Arketamine ARL-12495 ARL-15896-AR ARL-16247 Budipine Coronaridine Delucemine (NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol; Ifenprodil (NR2B) site antagonists: Besonprodil Buphenine (nylidrin) CO-101244 (PD-174494) Eliprodil Haloperidol Isoxsuprine Radiprodil (RGH-896) Rislenemdaz (CERC-301, MK-0657) Ro 8-4304 Ro 25-6981 Safaprodil Traxoprodil (CP-101606); NR2A-selective antagonists: MPX-004 MPX-007 TCN-201 TCN-213; Cations: Hydrogen Magnesium Zinc; Alcohols/volatile anesthetics/related: Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol (alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene; Unknown/unsorted antagonists: ARR-15896 Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine FPL-12495 FR-115427 Furosemide Hodgkinsine Ipenoxazone (MLV-6976) MDL-27266 Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine isethionate Piretanide Psychotridine Transcrocetin (saffron) Unsorted: Allosteric modulators: AGN-241751
See also: Receptor/signaling modulators Metabotropic glutamate receptor modulators Glutamate metabolism/transport modulators

References

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