Berupipam

Berupipam
Clinical data
Other names	NNC 22-0010; NNC-22-0010; NNC220010; NNC2210; NNC-2210
Drug class	Dopamine D1 receptor antagonist
Identifiers
	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;
CAS Number	150490-85-0;
PubChem CID	66002;
ChemSpider	59394;
UNII	420895MAOC;
ChEMBL	ChEMBL2106005;
Chemical and physical data
Formula	C19H19BrClNO2
Molar mass	408.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC2=CC(=C(C=C2[C@H](C1)C3=CC(=CC4=C3OCC4)Br)O)Cl;
	InChI InChI=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; Key:DIKLCFJDIZFAOM-INIZCTEOSA-N;

Berupipam (INNTooltip 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.^[1]^[2] It reached phase 1 clinical trials prior to the discontinuation of its development.^[1]

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.^[3]

Berupipam, in radiolabeled form, has been studied for use in positron emission tomography (PET) imaging.^[4]^[5]^[6] The drug was first described in the scientific literature by 1994.^[3]

References

^ ^a ^b "BERUPIPAM". Inxight Drugs. Retrieved 21 October 2024. 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
^ Zhang J, Xiong B, Zhen X, Zhang A (March 2009). "Dopamine D1 receptor ligands: where are we now and where are we going". Med Res Rev. 29 (2): 272–294. doi:10.1002/med.20130. PMID 18642350.272-294&rft.date=2009-03&rft_id=info:doi/10.1002/med.20130&rft_id=info:pmid/18642350&rft.aulast=Zhang&rft.aufirst=J&rft.au=Xiong, B&rft.au=Zhen, X&rft.au=Zhang, A&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">
^ ^a ^b Hall, Rodger (1994). "Defining new ground for the treatment of schizophrenia". Inpharma Weekly. 953 (953). Springer Science and Business Media LLC: 8–9. doi:10.2165/00128413-199409530-00015. ISSN 1173-8324. 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.8-9&rft.date=1994&rft_id=info:doi/10.2165/00128413-199409530-00015&rft.issn=1173-8324&rft.aulast=Hall&rft.aufirst=Rodger&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">
^ Prante O, Maschauer S, Banerjee A (2013). "Radioligands for the dopamine receptor subtypes". J Labelled Comp Radiopharm. 56 (3–4): 130–148. doi:10.1002/jlcr.3000. PMID 24285319.3–4&rft.pages=130-148&rft.date=2013&rft_id=info:doi/10.1002/jlcr.3000&rft_id=info:pmid/24285319&rft.aulast=Prante&rft.aufirst=O&rft.au=Maschauer, S&rft.au=Banerjee, A&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">
^ Banerjee A, Prante O (2012). "Subtype-selective dopamine receptor radioligands for PET imaging: current status and recent developments". Curr Med Chem. 19 (23): 3957–3966. doi:10.2174/092986712802002518. PMID 22780960.3957-3966&rft.date=2012&rft_id=info:doi/10.2174/092986712802002518&rft_id=info:pmid/22780960&rft.aulast=Banerjee&rft.aufirst=A&rft.au=Prante, O&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">
^ Foged C, Halldin C, Loc'h C, Mazière B, Karlsson P, Mazière M, Swahn CG, Farde L (August 1996). "11C- and 76Br-labelled NNC 22-0010, selective dopamine D1 receptor radioligands for PET". Nucl Med Biol. 23 (6): 837–844. doi:10.1016/0969-8051(96)00083-2. PMID 8940728.837-844&rft.date=1996-08&rft_id=info:doi/10.1016/0969-8051(96)50083-2&rft_id=info:pmid/8940728&rft.aulast=Foged&rft.aufirst=C&rft.au=Halldin, C&rft.au=Loc'h, C&rft.au=Mazière, B&rft.au=Karlsson, P&rft.au=Mazière, M&rft.au=Swahn, CG&rft.au=Farde, L&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">

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[InxightDrugs-1] "BERUPIPAM". Inxight Drugs. Retrieved 21 October 2024. 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

[ZhangXiongZhen2009-2] Zhang J, Xiong B, Zhen X, Zhang A (March 2009). "Dopamine D1 receptor ligands: where are we now and where are we going". Med Res Rev. 29 (2): 272–294. doi:10.1002/med.20130. PMID 18642350.272-294&rft.date=2009-03&rft_id=info:doi/10.1002/med.20130&rft_id=info:pmid/18642350&rft.aulast=Zhang&rft.aufirst=J&rft.au=Xiong, B&rft.au=Zhen, X&rft.au=Zhang, A&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">

[Hall1994-3] Hall, Rodger (1994). "Defining new ground for the treatment of schizophrenia". Inpharma Weekly. 953 (953). Springer Science and Business Media LLC: 8–9. doi:10.2165/00128413-199409530-00015. ISSN 1173-8324. 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.8-9&rft.date=1994&rft_id=info:doi/10.2165/00128413-199409530-00015&rft.issn=1173-8324&rft.aulast=Hall&rft.aufirst=Rodger&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">

[PranteMaschauerBanerjee2013-4] Prante O, Maschauer S, Banerjee A (2013). "Radioligands for the dopamine receptor subtypes". J Labelled Comp Radiopharm. 56 (3–4): 130–148. doi:10.1002/jlcr.3000. PMID 24285319.3–4&rft.pages=130-148&rft.date=2013&rft_id=info:doi/10.1002/jlcr.3000&rft_id=info:pmid/24285319&rft.aulast=Prante&rft.aufirst=O&rft.au=Maschauer, S&rft.au=Banerjee, A&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">

[BanerjeePrante2012-5] Banerjee A, Prante O (2012). "Subtype-selective dopamine receptor radioligands for PET imaging: current status and recent developments". Curr Med Chem. 19 (23): 3957–3966. doi:10.2174/092986712802002518. PMID 22780960.3957-3966&rft.date=2012&rft_id=info:doi/10.2174/092986712802002518&rft_id=info:pmid/22780960&rft.aulast=Banerjee&rft.aufirst=A&rft.au=Prante, O&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">

[FogedHalldinLoc'h1996-6] Foged C, Halldin C, Loc'h C, Mazière B, Karlsson P, Mazière M, Swahn CG, Farde L (August 1996). "11C- and 76Br-labelled NNC 22-0010, selective dopamine D1 receptor radioligands for PET". Nucl Med Biol. 23 (6): 837–844. doi:10.1016/0969-8051(96)00083-2. PMID 8940728.837-844&rft.date=1996-08&rft_id=info:doi/10.1016/0969-8051(96)50083-2&rft_id=info:pmid/8940728&rft.aulast=Foged&rft.aufirst=C&rft.au=Halldin, C&rft.au=Loc'h, C&rft.au=Mazière, B&rft.au=Karlsson, P&rft.au=Mazière, M&rft.au=Swahn, CG&rft.au=Farde, L&rfr_id=info:sid/en.wikipedia.org:Berupipam" class="Z3988">

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Berupipam

See also

References