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Revision as of 13:32, 15 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'CASNo').← Previous edit Latest revision as of 22:12, 17 July 2023 edit undoInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,071 editsmNo edit summary 
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{{chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 459888117
| Watchedfields = changed
⚫ | verifiedrevid = 460774030
⚫ | ImageFile = Dazoxiben.svg
⚫ | ImageSize =
⚫ | ImageAlt =
| PIN = 4-benzoic acid
⚫ | OtherNames =
⚫ |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 09ZFC7974Q | UNII = 09ZFC7974Q
| IUPHAR_ligand = 5175
⚫ | ImageFile = Dazoxiben.png
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | ImageSize =
⚫ | DrugBank = DB03052
⚫ | ImageAlt =
| IUPACName =
⚫ | OtherNames =
⚫ | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = <!-- blanked - oldvalue: 78218-09-4 -->
⚫ | DrugBank = DB03052
| PubChem =
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 267473 | ChEMBL = 267473
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 78218-09-4 --> | CASNo = 78218-09-4
| DrugBank = DB03052
| PubChem = 53001 | PubChem = 53001
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 47885 | ChemSpiderID = 47885
| SMILES = O=C(O)c2ccc(OCCn1ccnc1)cc2 | SMILES = O=C(O)c2ccc(OCCn1ccnc1)cc2
| InChI = 1/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16) | InChI = 1/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16)
| InChIKey = XQGZSYKGWHUSDH-UHFFFAOYAY | InChIKey = XQGZSYKGWHUSDH-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16) | StdInChI = 1S/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XQGZSYKGWHUSDH-UHFFFAOYSA-N | StdInChIKey = XQGZSYKGWHUSDH-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=12 | H=12 | N=2 | O=3
| Formula = C12H12N2O3
| Appearance =
| MolarMass = 232.2 g/mol
| Appearance = | Density =
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt = | Solubility =
}}
| Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt =
}}
}} }}


'''Dazoxiben''' is an orally active ].<ref>{{cite pmid|6337601}}</ref> It has shown a significant clinical improvement in patients with ].<ref>{{cite pmid|6337601}}</ref> '''Dazoxiben''' is an orally active ].<ref>{{Cite journal
| doi = 10.1111/j.1365-2125.1983.tb02119.x
| last1 = Belch | first1 = J. J.
| last2 = Cormie | first2 = J.
| last3 = Newman | first3 = P.
| last4 = McLaren | first4 = M.
| last5 = Barbenel | first5 = J.
| last6 = Capell | first6 = H.
| last7 = Leiberman | first7 = P.
| last8 = Forbes | first8 = C. D.
| last9 = Prentice | first9 = C. R.
| title = Dazoxiben, a thromboxane synthetase inhibitor, in the treatment of Raynaud's syndrome: A double-blind trial
| journal = British Journal of Clinical Pharmacology
| volume = 15 Suppl 1
| issue = Suppl 1
| pages = 113S–116S
| year = 1983
| pmid = 6337601
| pmc = 1427695
}}</ref> It has shown a significant clinical improvement in patients with ].<ref>{{Cite journal
| doi = 10.1111/j.1365-2125.1983.tb02119.x
| last1 = Belch | first1 = J. J.
| last2 = Cormie | first2 = J.
| last3 = Newman | first3 = P.
| last4 = McLaren | first4 = M.
| last5 = Barbenel | first5 = J.
| last6 = Capell | first6 = H.
| last7 = Leiberman | first7 = P.
| last8 = Forbes | first8 = C. D.
| last9 = Prentice | first9 = C. R.
| title = Dazoxiben, a thromboxane synthetase inhibitor, in the treatment of Raynaud's syndrome: A double-blind trial
| journal = British Journal of Clinical Pharmacology
| volume = 15 Suppl 1
| issue = Suppl 1
| pages = 113S–116S
| year = 1983
| pmid = 6337601
| pmc = 1427695
}}</ref>

==Synthesis==
|assign=]|inventor1-last=Cross|inventor1-first=Peter Edward|inventor2-last=Dickinson|inventor2-first=Roger Peter}}</ref><ref>{{cite journal|doi=10.1007/BF02226528|title=Simplified synthesis of dazoxiben|journal=Pharmaceutical Chemistry Journal|volume=29|issue=2|pages=139|year=1995|last1=Kochergin|first1=P. M.|last2=Palei|first2=R. M.|last3=Balandina|first3=L. V.|last4=Kharitonova|first4=A. E.|last5=Kravchenko|first5=A. N.|last6=Persanova|first6=L. V.|last7=Govorukhina|first7=E. I.|last8=Frolova|first8=M. A.|s2cid=37387182 }}</ref><ref>{{cite journal|doi=10.1021/jm00142a005|pmid=7199088|title=Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives|journal=Journal of Medicinal Chemistry|volume=24|issue=10|pages=1139–1148|year=1981|last1=Iizuka|first1=Kinji|last2=Akahane|first2=Kenji|last3=Momose|first3=Denichi|last4=Nakazawa|first4=Masayuki|last5=Tanouchi|first5=Tadao|last6=Kawamura|first6=Masanori|last7=Ohyama|first7=Isao|last8=Kajiwara|first8=Ikuo|last9=Iguchi|first9=Yohichi}}</ref><ref>{{cite journal|doi=10.1021/jm00148a009|pmid=3930740|title=Selective thromboxane synthetase inhibitors. 1. 1--1H-imidazoles|journal=Journal of Medicinal Chemistry|volume=28|issue=10|pages=1427–1432|year=1985|last1=Cross|first1=Peter E.|last2=Dickinson|first2=Roger P.|last3=Parry|first3=M. John|last4=Randall|first4=Michael J.}}</ref>]]
One convenient synthesis starts with the O-chloroethyl ] of p-hydroxybenzamide and proceeds bydisplacement with ] to give '''2'''. ] of the amide function completes the synthesis of dazoxiben.


==References== ==References==
{{reflist}} {{Reflist|2}}


{{Antithrombotics}} {{Antithrombotics}}
{{Prostanoidergics}}

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