Dazoxiben

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460774030

| ImageFile = Dazoxiben.svg

| ImageSize =

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| PIN = 4-[2-(1H-Imidazol-1-yl)ethoxy]benzoic acid

| OtherNames =

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 09ZFC7974Q

| IUPHAR_ligand = 5175

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB03052

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 267473

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 78218-09-4

| PubChem = 53001

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 47885

| 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)

| InChIKey = XQGZSYKGWHUSDH-UHFFFAOYAY

| 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XQGZSYKGWHUSDH-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=12 | H=12 | N=2 | O=3

| Appearance =

| Density =

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|Section3={{Chembox Hazards

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Dazoxiben is an orally active thromboxane synthase inhibitor.{{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

}} It has shown a significant clinical improvement in patients with Raynaud's syndrome.{{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

}}

Synthesis

File:Dazoxiben synthesis.svg|inventor1-last=Cross|inventor1-first=Peter Edward|inventor2-last=Dickinson|inventor2-first=Roger Peter}}{{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 }}{{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}}{{cite journal|doi=10.1021/jm00148a009|pmid=3930740|title=Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-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.}}]]

One convenient synthesis starts with the O-chloroethyl ether of p-hydroxybenzamide and proceeds bydisplacement with imidazole to give 2. Hydrolysis of the amide function completes the synthesis of dazoxiben.

References

{{Reflist|2}}

{{Antithrombotics}}

{{Prostanoidergics}}

Category:Antithrombotic agents

Category:Imidazoles

Category:Benzoic acids

Category:Ethanolamines

{{blood-drug-stub}}