Fenobam
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Names |
IUPAC name
1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4H-imidazol-2-yl)urea
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Identifiers |
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57653-26-6 Y |
ChEMBL |
ChEMBL239800 N |
ChemSpider |
142953 N |
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1434 |
Jmol 3D model |
Interactive image |
MeSH |
fenobam |
PubChem |
162834 |
UNII |
078RCY7I27 N |
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InChI=1S/C11H11ClN4O2/c1-16-6-9(17)14-10(16)15-11(18)13-8-4-2-3-7(12)5-8/h2-5H,6H2,1H3,(H2,13,14,15,17,18) N
Key: DWPQODZAOSWNHB-UHFFFAOYSA-N N
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InChI=1/C11H11ClN4O2/c1-16-6-9(17)14-10(16)15-11(18)13-8-4-2-3-7(12)5-8/h2-5H,6H2,1H3,(H2,13,14,15,17,18)
Key: DWPQODZAOSWNHB-UHFFFAOYAC
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O=C1CN(C)C(NC(NC2=CC=CC(Cl)=C2)=O)=N1
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Properties |
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C11H11ClN4O2 |
Molar mass |
266.684 |
Vapor pressure |
{{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is YN ?) |
Infobox references |
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Fenobam is an imidazole derivative developed by McNeil Laboratories in the late 1970s as a novel anxiolytic drug with an at-the-time-unidentified molecular target in the brain. Subsequently, it was determined that fenobam acts as a potent and selective negative allosteric modulator of the metabotropic glutamate receptor subtype mGluR5,[1][2] and it has been used as a lead compound for the development of a range of newer mGluR5 antagonists.[3][4][5][6]
Fenobam has anxiolytic effects comparable to those of benzodiazepine drugs,[1][7][8] but was never commercially marketed for the treatment of anxiety due to dose-limiting side effects such as amnesia and psychotomimetic symptoms.[9][10] Following the discovery of its activity as a potent negative allosteric modulator of mGluR5, fenobam has been re-investigated for many applications, with its profile of combined antidepressant, anxiolytic, analgesic and anti-addictive effects potentially useful given the common co-morbidity of these symptoms.[11][12] It has also shown promising initial results in the treatment of fragile X syndrome.[13] It was developed by a team at McNeil Laboratories in the 1970s.[14]
Chemistry
Fenobam is known to exist in five crystalline forms, all of them exhibiting a tautomeric structure with the proton attached to the five membered ring nitrogen. [15]
References
- ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
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- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ US Patent 3983135 4-Oxo-2-imidazolidinylidene ureas
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
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Receptor
(ligands) |
AMPA |
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NMDA |
- Agonists: Glutamate/active 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
- CCG
- D-Alanine
- D-Cycloserine
- D-Serine
- DHPG
- Glycine
- HA-966
- L-687,414
- L-Alanine
- L-Serine
- Milacemide
- Neboglamine
- NRX-1074
- Rapastinel (GLYX-13)
- Sarcosine; Polyamine site agonists: Spermidine
- Spermine
- Antagonists: Competitive antagonists: AP5 (APV)
- AP7
- CGP-37849
- CGP-39551
- CGP-39653
- CGP-40116
- CGS-19755
- CPP
- LY-233,053
- LY-235,959
- LY-274,614
- MDL-100,453
- Midafotel (d-CPPene)
- NPC-12,626
- NPC-17,742
- PBPD
- PEAQX
- Perzinfotel
- PPDA
- SDZ-220581
- Selfotel; Noncompetitive antagonists: ARR-15,896
- Caroverine
- Dexanabinol
- FPL-12495
- FR-115,427
- Hodgkinsine
- Magnesium
- MDL-27,266
- NPS-1506
- Psychotridine
- Zinc; Uncompetitive pore blockers: 2-MDP
- 3-HO-PCP
- 3-MeO-PCE
- 3-MeO-PCMo
- 3-MeO-PCP
- 4-MeO-PCP
- 8A-PDHQ
- 18-MC
- α-Endopsychosin
- Alaproclate
- Amantadine
- Aptiganel
- Arketamine
- ARL-12,495
- ARL-15,896-AR
- ARL-16,247
- Budipine
- Conaridine
- Delucemine
- Dexoxadrol
- Dextrallorphan
- Dieticyclidine
- Diphenidine
- Dizocilpine
- Ephenidine
- Esketamine
- Etoxadrol
- Eticyclidine
- Fluorolintane
- Gacyclidine
- Ibogaine
- Ibogamine
- Indantadol
- Ketamine
- Ketobemidone
- Lanicemine
- Loperamide
- Memantine
- Methadone (Levomethadone)
- Methorphan (Dextromethorphan
- Levomethorphan)
- Methoxetamine
- Methoxphenidine
- Milnacipran
- Morphanol (Dextrorphan
- Levorphanol)
- NEFA
- Neramexane
- Nitromemantine
- Nitrous oxide
- Noribogaine
- Norketamine
- Orphenadrine
- PCPr
- Pethidine (meperidine)
- Phencyclamine
- Phencyclidine
- Propoxyphene
- Remacemide
- Rhynchophylline
- Rimantadine
- Rolicyclidine
- Sabeluzole
- Tabernanthine
- Tenocyclidine
- Tiletamine
- Tramadol
- Xenon; Glycine site antagonists: 4-Cl-KYN (AV-101)
- 5,7-DCKA
- 7-CKA
- ACC
- ACEA-1011
- ACEA-1328
- AV-101
- Carisoprodol
- CGP-39653
- CNQX
- DNQX
- Felbamate
- Gavestinel
- GV-196,771
- Kynurenic acid
- Kynurenine
- L-689,560
- L-701,324
- Licostinel (ACEA-1021)
- LU-73,068
- MDL-105,519
- Meprobamate
- MRZ 2/576
- PNQX
- ZD-9379; NR2B subunit antagonists: Besonprodil
- CERC-301 (MK-0657)
- CO-101,244 (PD-174,494)
- Eliprodil
- Haloperidol
- Ifenprodil
- Isoxsuprine
- Nylidrin
- Ro8-4304
- Ro25-6981
- Traxoprodil; Polyamine site antagonists: Arcaine
- Co 101676
- Diaminopropane
- Diethylenetriamine
- Huperzine A
- Putrescine
- Ro 25-6981; Unclassified/unsorted antagonists: Bumetanide
- Chloroform
- Cyclopropane
- D-αAA
- Diethyl ether
- Enflurane
- Ethanol
- Flufenamic acid
- Flupirtine
- Furosemide
- Halothane
- Isoflurane
- Metaphit
- Methoxyflurane
- Niflumic acid
- Piretanide
- Toluene
- Transcrocetin (saffron)
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- Xylene
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Kainate |
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mGlu1 |
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mGlu2 |
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mGlu3 |
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mGlu4 |
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mGlu5 |
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mGlu6 |
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mGlu7 |
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mGlu8 |
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Transporter
(blockers) |
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Enzyme
(inhibitors) |
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Others |
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