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Saving copy of the {{drugbox}} taken from revid 448523438 of page Tesofensine for the Chem/Drugbox validation project (updated: 'CAS_number').
 
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{{Short description|Chemical compound with anti-parasitic properties}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Tesofensine|oldid=448523438}} 448523438] of page [[Tesofensine]] with values updated to verified values.}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
⚫
| verifiedrevid = 447923418
| Watchedfields = changed
| IUPAC_name = (1''R'',2''R'',3''S'')-3-(3,4-dichlorophenyl)-2-(ethoxymethyl)-8-methyl-8-azabicyclo[3.2.1]octane
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| verifiedrevid = 470603052
| image = Tesofensine chemical structure.png
| IUPAC_name = [1-(2,2-dichloroacetyl)-3,4-dihydro-2H-quinolin-6-yl] furan-2-carboxylate
| image = Quinfamide.svg
| width = 170
| width = 170

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| pregnancy_AU =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_US =
| pregnancy_category = Not applicable
| pregnancy_category =
| legal_AU =
| legal_AU =
| legal_CA =
| legal_CA =
| legal_UK =
| legal_UK =
| legal_US =
| legal_US =
| legal_status = Investigatory new drug
| legal_status =
| routes_of_administration = Oral
| routes_of_administration = Oral

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability = 90%
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism = 15&ndash;20% renal; hepatic: CYP3A4
| metabolism =
| elimination_half-life = 220 hours
| elimination_half-life =
| excretion = Not applicable
| excretion =

<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 195875-84-4 -->
| ATC_prefix = None
| ATC_prefix = None
| ATC_suffix =
| ATC_suffix =
| CAS_number = 62265-68-3
| PubChem = 11522724
| PubChem = 71743
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 9697511
| ChemSpiderID = 64787
| smiles = C1CC2=C(C=CC(=C2)OC(=O)C3=CC=CO3)N(C1)C(=O)C(Cl)Cl
| StdInChI = 1S/C16H13Cl2NO4/c17-14(18)15(20)19-7-1-3-10-9-11(5-6-12(10)19)23-16(21)13-4-2-8-22-13/h2,4-6,8-9,14H,1,3,7H2
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
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| StdInChIKey = SBJGFIXQRZOVTO-UHFFFAOYSA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BLH9UKX9V1
| UNII = O1ZB1046R1
| KEGG = D00641

<!--Chemical data-->
<!--Chemical data-->
| C=17 | H=23 | Cl=2 | N=1 | O=1
| C=16 | H=13 | Cl=2 | N=1 | O=4
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| melting_point =
| molecular_weight = 328.277 g/mol
⚫
| melting_high =
| smiles = Clc1ccc(cc1Cl)[C@H]3CC2N(C)C(CC2)[C@@H]3COCC
| InChI = 1/C17H23Cl2NO/c1-3-21-10-14-13(9-12-5-7-17(14)20(12)2)11-4-6-15(18)16(19)8-11/h4,6,8,12-14,17H,3,5,7,9-10H2,1-2H3/t12?,13-,14-,17?/m1/s1
| InChIKey = VCVWXKKWDOJNIT-YXXKGXSTBF
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H23Cl2NO/c1-3-21-10-14-13(9-12-5-7-17(14)20(12)2)11-4-6-15(18)16(19)8-11/h4,6,8,12-14,17H,3,5,7,9-10H2,1-2H3/t12?,13-,14-,17?/m1/s1
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChIKey = VCVWXKKWDOJNIT-YXXKGXSTSA-N
⚫
| melting_point =
⚫
| melting_high =
}}
}}

'''Quinfamide''' is a drug that has anti-parasitic properties.<ref name="pmid12139216">{{cite journal | vauthors = Davila-Gutierrez CE, Vasquez C, Trujillo-Hernandez B, Huerta M | title = Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children | journal = The American Journal of Tropical Medicine and Hygiene | volume = 66 | issue = 3 | pages = 251–4 | date = March 2002 | pmid = 12139216 | doi = 10.4269/ajtmh.2002.66.251 | doi-access = free }}</ref>

== Synthesis ==
Quinfamide is one of a relatively small family of [[wikt:antiamoebic|antiamoebic]] compounds containing a dichloroacetamide function.{{cn|date=December 2022}}
[[File:Quinfamide synthesis.svg|thumb|center|400px|Quinfamide synthesis:<ref>{{cite patent|country=US|number=3997542|pubdate=1976-12-14|assign1=[[Sterling_Drug|Sterling Drug Inc.]]|title=1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and esters thereof|inventor1-last=Bailey|inventor1-first=Denis Mahlon}}</ref><ref>{{cite journal | vauthors = Bailey DM, Mount EM, Siggins J, Carlson JA, Yarinsky A, Slighter RG | title = 1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 5 | pages = 599–601 | date = May 1979 | pmid = 458814 | doi = 10.1021/jm00191a031 }}</ref>]]
The synthesis begins by amidation of 6-hydroxytetrahydroquinoline with [[dichloroacetyl chloride]]. The sequence is completed by acylation with [[2-Furoyl chloride|2-furoyl chloride]].

== References ==
{{reflist}}

[[Category:Antiprotozoal agents]]
[[Category:Tetrahydroquinolines]]
[[Category:Amides]]
[[Category:2-Furyl compounds]]
[[Category:Phenol esters]]
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