Atiprosin: Difference between revisions

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| IUPAC_name = (4aR,12bS)-1-ethyl-12-methyl-4-(propan-2-yl)-1,2,3,4,4a,5,6,12b-octahydropyrazino[2',3':3,4]pyrido[1,2-a]indole
| Watchedfields = changed
| image = Atiprosin_structure.png
| verifiedrevid = 458780782
| IUPAC_name = (4a''R'',12b''S'')-1-ethyl-12-methyl-4-(propan-2-yl)-1,2,3,4,4a,5,6,12b-octahydropyrazino[2',3':3,4]pyrido[1,2-a]indole
| image = Atiprosin Structure.svg
| width =


<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| legal_status = Uncontrolled
| legal_status =
| routes_of_administration = Oral
| routes_of_administration = [[Oral administration|Oral]]


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 89303-63-9 -->
| CAS_number = 89303-63-9
| ATC_prefix = none
| ATC_prefix = none
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H29N3/c1-5-21-12-13-22(14(2)3)18-10-11-23-17-9-7-6-8-16(17)15(4)19(23)20(18)21/h6-9,14,18,20H,5,10-13H2,1-4H3/t18-,20+/m1/s1
| StdInChI = 1S/C20H29N3/c1-5-21-12-13-22(14(2)3)18-10-11-23-17-9-7-6-8-16(17)15(4)19(23)20(18)21/h6-9,14,18,20H,5,10-13H2,1-4H3/t18-,20+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WXNVFYIBELASJW-QUCCMNQESA-N
| StdInChIKey = WXNVFYIBELASJW-QUCCMNQESA-N
| PubChem = 71770
| PubChem = 71770
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 64808
| ChemSpiderID = 64808
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2111172
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ALS52889WF
| UNII = ALS52889WF
| synonyms = AY-28,228


<!--Chemical data-->
<!--Chemical data-->
| C=20 | H=29 | N=3
| C=20 | H=29 | N=3
| SMILES = n23c1ccccc1c(c2[C@H]4N(CCN([C@@H]4CC3)C(C)C)CC)C
| molecular_weight = 311.46 g/mol
| smiles = n23c1ccccc1c(c2[C@H]4N(CCN([C@@H]4CC3)C(C)C)CC)C
}}
}}


'''Atiprosin''' ('''AY-28,228''') is an [[antihypertensive]] [[drug|agent]] which acts as a [[binding selectivity|selective]] [[alpha-1 adrenergic receptor|α<sub>1</sub>-adrenergic receptor]] [[receptor antagonist|antagonist]].<ref name="isbn0-412-46630-9">{{cite book | author = David J. Triggle | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | pages = | isbn = 0-412-46630-9 | oclc = | doi = | url = http://books.google.com/?id=DeX7jgInYFMC&lpg=PA189&dq=atiprosin&pg=PA189#v=onepage&q}}</ref><ref name="pmid3806618">{{cite journal | author = Jirkovsky I, Santroch G, Baudy R, Oshiro G | title = Octahydropyrazino[2',3':3,4]pyrido[1,2-a]indoles. A new class of potent antihypertensive agents | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 2 | pages = 388–94 | year = 1987 | month = February | pmid = 3806618 | doi = 10.1021/jm00385a022| url = }}</ref><ref name="pmid2444771">{{cite journal | author = Grimes D, Rimele TJ, Henry DE, ''et al.'' | title = In vitro isolated tissue studies with atiprosin (AY-28,228): a new antihypertensive compound | journal = Journal of Cardiovascular Pharmacology | volume = 10 | issue = 3 | pages = 249–58 | year = 1987 | month = September | pmid = 2444771 | doi = 10.1097/00005344-198709000-00001| url = }}</ref><ref name="pmid2444784">{{cite journal | author = Oshiro G, Wojdan A, Klein M, Metcalf G | title = Antihypertensive and hypotensive actions of atiprosin (AY-28,228) in rats, dogs, and monkeys | journal = Journal of Cardiovascular Pharmacology | volume = 10 | issue = 3 | pages = 341–9 | year = 1987 | month = September | pmid = 2444784 | doi = 10.1097/00005344-198709000-00014| url = }}</ref> It also possesses some [[antihistamine]] activity, though it is some 15-fold weaker in this regard than as an [[alpha blocker]].<ref name="pmid2444771"/> It was never marketed.<ref name="isbn0-412-46630-9"/>
'''Atiprosin''' (developmental code name '''AY-28,228''') is an [[antihypertensive]] [[drug|agent]] which acts as a [[binding selectivity|selective]] [[alpha-1 adrenergic receptor|α<sub>1</sub>-adrenergic receptor]] [[receptor antagonist|antagonist]].<ref name="isbn0-412-46630-9">{{cite book | author = David J. Triggle | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&q=atiprosin&pg=PA189}}</ref><ref name="pmid3806618">{{cite journal |vauthors=Jirkovsky I, Santroch G, Baudy R, Oshiro G | title = Octahydropyrazino[2',3':3,4]pyrido[1,2-a]indoles. A new class of potent antihypertensive agents | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 2 | pages = 388–94 |date=February 1987 | pmid = 3806618 | doi = 10.1021/jm00385a022}}</ref><ref name="pmid2444771">{{cite journal |vauthors=Grimes D, Rimele TJ, Henry DE | title = In vitro isolated tissue studies with atiprosin (AY-28,228): a new antihypertensive compound | journal = Journal of Cardiovascular Pharmacology | volume = 10 | issue = 3 | pages = 249–58 |date=September 1987 | pmid = 2444771 | doi = 10.1097/00005344-198709000-00001| s2cid = 9361176 |display-authors=etal| doi-access = free }}</ref><ref name="pmid2444784">{{cite journal |vauthors=Oshiro G, Wojdan A, Klein M, Metcalf G | title = Antihypertensive and hypotensive actions of atiprosin (AY-28,228) in rats, dogs, and monkeys | journal = Journal of Cardiovascular Pharmacology | volume = 10 | issue = 3 | pages = 341–9 |date=September 1987 | pmid = 2444784 | doi = 10.1097/00005344-198709000-00014| s2cid = 19086175 | doi-access = free }}</ref> It also possesses some [[antihistamine]] activity, though it is some 15-fold weaker in this regard than as an [[alpha blocker]].<ref name="pmid2444771"/> It was never marketed.<ref name="isbn0-412-46630-9"/>


== Synthesis ==
==See also==
[[File:Atiprosin.png|450px]]<ref>{{Cite journal|journal=Journal of Medical Chemistry|year=1987|volume=30|issue=2|pages=388–394|last=Jirkovsky|first=Ivo|coauthors=George Santroch, Reinhardt Baudy, George Oshiro|title=Octahydropyrazino[2',3':3,4]pyrido[1,2-a]indoles. A new class of potent antihypertensive agents|doi=10.1021/jm00385a022|pmid=3806618}}</ref>

== See also ==
* [[Prazosin]]
* [[Prazosin]]
* [[Ketanserin]]
* [[Ketanserin]]


== References ==
==References==
{{Reflist}}
{{Reflist}}

==External links==
* {{Commonscatinline}}


{{Antihypertensives}}
{{Antihypertensives}}
{{Adrenergic receptor modulators}}
{{Adrenergics}}
{{Histamine receptor modulators}}
{{Histaminergics}}
{{Tricyclics}}
{{Tricyclics}}


[[Category:Alpha blockers]]
[[Category:Abandoned drugs]]
[[Category:Alpha-1 blockers]]
[[Category:Antihistamines]]
[[Category:Antihypertensive agents]]
[[Category:Antihypertensive agents]]
[[Category:Indoles]]
[[Category:Isopropyl compounds]]
[[Category:Piperazines]]


{{Antihypertensive-stub}}