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{{Short description|Chemical compound}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 443333402 |
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| verifiedrevid = 448211529 |
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| IUPAC_name = 5-(3-fluorophenyl)-2,4-dimethyl-2,4-dihydro-3''H''-1,2,4-triazole-3-thione |
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| IUPAC_name = 5-(3-fluorophenyl)-2,4-dimethyl-2,4-dihydro-3''H''-1,2,4-triazole-3-thione |
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| image = Suritozole.svg |
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| image = Suritozole.svg |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 110623-33-1 |
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| CAS_number = 110623-33-1 |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D05980 |
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| KEGG = D05980 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 23743 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=10 | H=10 | F=1 | N=3 | S=1 |
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| C=10 | H=10 | F=1 | N=3 | S=1 |
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| molecular_weight = 223.269 g/mol |
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| smiles = Cn1c(=S)n(C)nc1-c2cccc(F)c2 |
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| smiles = Cn1c(=S)n(C)nc1-c2cccc(F)c2 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C10H10FN3S/c1-13-9(12-14(2)10(13)15)7-4-3-5-8(11)6-7/h3-6H,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = IWDUZEHNLHFBRZ-UHFFFAOYSA-N |
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}} |
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'''Suritozole''' ('''MDL 26,479''') is an investigational ]. It acts as a partial ] at the ] site on the GABA<sub>A</sub> ion channel compex, but does not have either ] or ] effects, unlike other BZD inverse agonists such as ].<ref name="pmid1330168">{{cite journal |author=Miller JA, Dudley MW, Kehne JH, Sorensen SM, Kane JM |title=MDL 26,479: a potential cognition enhancer with benzodiazepine inverse agonist-like properties |journal=Br. J. Pharmacol. |volume=107 |issue=1 |pages=78–86 |year=1992 |month=September |pmid=1330168 |pmc=1907590 |doi= |url=}}</ref> It was investigated for the treatment of ] and ],<ref name="pmid9158880">{{cite journal |author=Robbins DK, Hutcheson SJ, Miller TD, Green VI, Bhargava VO, Weir SJ |title=Pharmacokinetics of MDL 26479, a novel benzodiazepine inverse agonist, in normal volunteers |journal=Biopharm Drug Dispos |volume=18 |issue=4 |pages=325–34 |year=1997 |month=May |pmid=9158880|doi=10.1002/(SICI)1099-081X(199705)18:4<325::AID-BDD21>3.0.CO;2-1}}</ref> but clinical development seems to have been discontinued. |
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'''Suritozole''' ('''MDL 26,479''') is an investigational ]. It acts as a partial ] at the ] site on the GABA<sub>A</sub> ion channel complex, but does not have either ] or ] effects, unlike other BZD inverse agonists such as ].<ref name="pmid1330168">{{cite journal | vauthors = Miller JA, Dudley MW, Kehne JH, Sorensen SM, Kane JM | title = MDL 26,479: a potential cognition enhancer with benzodiazepine inverse agonist-like properties | journal = British Journal of Pharmacology | volume = 107 | issue = 1 | pages = 78–86 | date = September 1992 | pmid = 1330168 | pmc = 1907590 | doi = 10.1111/j.1476-5381.1992.tb14466.x }}</ref> It was investigated for the treatment of ] and ],<ref name="pmid9158880">{{cite journal | vauthors = Robbins DK, Hutcheson SJ, Miller TD, Green VI, Bhargava VO, Weir SJ | title = Pharmacokinetics of MDL 26479, a novel benzodiazepine inverse agonist, in normal volunteers | journal = Biopharmaceutics & Drug Disposition | volume = 18 | issue = 4 | pages = 325–334 | date = May 1997 | pmid = 9158880 | doi = 10.1002/(SICI)1099-081X(199705)18:4<325::AID-BDD21>3.0.CO;2-1 }}</ref> but clinical development seems to have been discontinued. |
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==Synthesis== |
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] |
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The reaction between monomethylhydrazine ('''1''') and methyl isothiocyanate (Trapex) ('''2''') gave 2,4-dimethylthiosemicarbazide ('''3'''). Amide formation with 3-fluorobenzoyl chloride ('''4''') yielded 1-(3-fluorobenzoyl)-2,4-dimethylthiosemicarbazide ('''5'''). Cyclization to Suritozole ('''6'''). |
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== See also == |
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* ] |
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* ] |
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==References== |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{Psychostimulants, agents used for ADHD and nootropics}} |
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{{GABAergics}} |
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{{GABAergics}} |
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{{nervous-system-drug-stub}} |
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{{nervous-system-drug-stub}} |