Berupipam

{{Short description|Abandoned D1 receptor antagonist}}

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| class = Dopamine D₁ receptor antagonist

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| CAS_number = 150490-85-0

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| PubChem = 66002

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| ChemSpiderID = 59394

| UNII = 420895MAOC

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| ChEMBL = 2106005

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| synonyms = NNC 22-0010; NNC-22-0010; NNC220010; NNC2210; NNC-2210

| IUPAC_name = (5S)-5-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-8-chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol

| C=19 | H=19 | Br=1 | Cl=1 | N=1 | O=2

| SMILES = CN1CCC2=CC(=C(C=C2[C@H](C1)C3=CC(=CC4=C3OCC4)Br)O)Cl

| StdInChI = 1S/C19H19BrClNO2/c1-22-4-2-11-7-17(21)18(23)9-14(11)16(10-22)15-8-13(20)6-12-3-5-24-19(12)15/h6-9,16,23H,2-5,10H2,1H3/t16-/m0/s1

| StdInChIKey = DIKLCFJDIZFAOM-INIZCTEOSA-N

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Berupipam ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code name NNC 22-0010) is a selective dopamine D₁ receptor antagonist of the benzazepine group which was under development for the treatment of psychotic disorders but was never marketed.{{cite web | title=BERUPIPAM | website=Inxight Drugs | url=https://drugs.ncats.io/substance/420895MAOC | access-date=21 October 2024 | quote=Berupipam (also known as NNC 22-0010), a dopamine antagonist with a high affinity and selectivity for D1 receptor has been studied for patients with psychotic disorders. Berupipam participated in phase I clinical trials; however, further development of this drug was discontinued}}{{cite journal | vauthors = Zhang J, Xiong B, Zhen X, Zhang A | title = Dopamine D1 receptor ligands: where are we now and where are we going | journal = Med Res Rev | volume = 29 | issue = 2 | pages = 272–294 | date = March 2009 | pmid = 18642350 | doi = 10.1002/med.20130 | url = }} It reached phase 1 clinical trials prior to the discontinuation of its development.

Berupipam and closely related dopamine D₁ receptor antagonists were reported to have been generally well-tolerated in clinical trials, but side effects included restlessness, drowsiness, other central nervous system-related symptoms, and orthostatic hypotension.{{cite journal | last=Hall | first=Rodger | title=Defining new ground for the treatment of schizophrenia | journal=Inpharma Weekly | publisher=Springer Science and Business Media LLC | volume=953 | issue= 953| year=1994 | issn=1173-8324 | doi=10.2165/00128413-199409530-00015 | pages=8–9 | quote=D1-antagonists are an area of active research. Although no results of widespread clinical testing have yet been published. phase I clinical trials presented by Dr M Sloth-Nielson from Novo Nordisk suggest that further investigation of the 3 novel drugs NNC 01-0687, NNC 01-0756 [odapipam] and NNC 22-0010 is warranted. The drugs were generally well tolerated, with restlessness, drowsiness and other CNS-related symptoms being the main effects observed. NNC 22-0010 50mg produced a moderate orthostatic hypotension in 2 volunteers.}}

Berupipam, in radiolabeled form, has been studied for use in positron emission tomography (PET) imaging.{{cite journal | vauthors = Prante O, Maschauer S, Banerjee A | title = Radioligands for the dopamine receptor subtypes | journal = J Label Compd Radiopharm | volume = 56 | issue = 3–4 | pages = 130–148 | date = 2013 | pmid = 24285319 | doi = 10.1002/jlcr.3000 | url = }}{{cite journal | vauthors = Banerjee A, Prante O | title = Subtype-selective dopamine receptor radioligands for PET imaging: current status and recent developments | journal = Curr Med Chem | volume = 19 | issue = 23 | pages = 3957–3966 | date = 2012 | pmid = 22780960 | doi = 10.2174/092986712802002518 | url = }}{{cite journal | vauthors = Foged C, Halldin C, Loc'h C, Mazière B, Karlsson P, Mazière M, Swahn CG, Farde L | title = 11C- and 76Br-labelled NNC 22-0010, selective dopamine D1 receptor radioligands for PET | journal = Nucl Med Biol | volume = 23 | issue = 6 | pages = 837–844 | date = August 1996 | pmid = 8940728 | doi = 10.1016/0969-8051(96)00083-2 | url = }} The drug was first described in the scientific literature by 1994.