Odapipam

{{Short description|Abandoned D1 receptor antagonist}}

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| class = Dopamine D₁ receptor antagonist

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| CAS_number = 131796-63-9

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| PubChem = 132421

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| ChemSpiderID = 116932

| UNII = 847PQF7ZN6

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| ChEMBL = 2106649

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| synonyms = NNC 01-0756; NNC-01-0756; NNC-010756; NNC010756; NNC01-0756; NNC-756; NNC756; NNC 0756; NNC0756; NO-756; NO756

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

| C=19 | H=20 | Cl=1 | N=1 | O=2

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

| StdInChI = 1S/C19H20ClNO2/c1-21-7-5-13-9-17(20)18(22)10-15(13)16(11-21)14-4-2-3-12-6-8-23-19(12)14/h2-4,9-10,16,22H,5-8,11H2,1H3/t16-/m1/s1

| StdInChIKey = SKMVRXPBCSTNKE-MRXNPFEDSA-N

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Odapipam ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code names NNC 01-0756, NNC-756, NO-756) is a selective D₁ receptor antagonist of the benzazepine group which was investigated as a potential antipsychotic but was never marketed.{{cite journal | vauthors = Shen WW | title = A history of antipsychotic drug development | journal = Compr Psychiatry | volume = 40 | issue = 6 | pages = 407–414 | date = 1999 | pmid = 10579370 | doi = 10.1016/s0010-440x(99)90082-2 | url = }}{{cite journal | vauthors = Seamans JK, Yang CR | title = The principal features and mechanisms of dopamine modulation in the prefrontal cortex | journal = Prog Neurobiol | volume = 74 | issue = 1 | pages = 1–58 | date = September 2004 | pmid = 15381316 | doi = 10.1016/j.pneurobio.2004.05.006 | url = }}

It has more than 5,000-fold selectivity for the dopamine D₁ receptor (K_i = 0.17{{nbsp}}nM) over the dopamine D₂ receptor (K_i = 942{{nbsp}}nM).{{cite journal | vauthors = Neumann J, Hofmann B, Dhein S, Gergs U | title = Role of Dopamine in the Heart in Health and Disease | journal = Int J Mol Sci | volume = 24 | issue = 5 | date = March 2023 | page = 5042 | pmid = 36902474 | pmc = 10003060 | doi = 10.3390/ijms24055042 | doi-access = free | url = }} Its affinities for other dopamine receptors, such as the dopamine D₅ receptor, were not reported. In addition to the dopamine D₁ receptor, odapipam showed relatively high affinity for the serotonin 5-HT₂ receptor (K_i = 4.5{{nbsp}}nM; 26-fold lower than for the D₁ receptor).

The drug was first described in the scientific literature by 1988.{{cite journal | vauthors = Andersen PH, Grønvald FC, Hohlweg R, Hansen LB, Guddal E, Braestrup C, Nielsen EB | title = NNC-112, NNC-687 and NNC-756, new selective and highly potent dopamine D1 receptor antagonists | journal = Eur J Pharmacol | volume = 219 | issue = 1 | pages = 45–52 | date = August 1992 | pmid = 1397049 | doi = 10.1016/0014-2999(92)90578-r | url = }}{{cite journal | vauthors = Waddington JL | title = Functional interactions between D-1 and D-2 dopamine receptor systems: their role in the regulation of psychomotor behaviour, putative mechanisms, and clinical relevance | journal = J Psychopharmacol | volume = 3 | issue = 2 | pages = 54–63 | date = January 1989 | pmid = 22156499 | doi = 10.1177/026988118900300202 | url = }}