:BIBP-3226
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 477369930
| IUPAC_name = (2R)-5-(diaminomethylideneamino)-2-([2,2-diphenylacetyl]amino)-N-[(4-hydroxyphenyl)methyl]pentanamide
| image = BIBP-3226 Structure.svg
| width = 300
| tradename =
| pregnancy_AU =
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| legal_AU =
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| legal_US =
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| routes_of_administration =
| bioavailability =
| protein_bound =
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| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 159013-54-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RG9766UGZ8
| ATC_prefix =
| ATC_suffix =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 332347
| PubChem = 5311023
| IUPHAR_ligand = 1485
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4470561
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C27H31N5O3/c28-27(29)30-17-7-12-23(25(34)31-18-19-13-15-22(33)16-14-19)32-26(35)24(20-8-3-1-4-9-20)21-10-5-2-6-11-21/h1-6,8-11,13-16,23-24,33H,7,12,17-18H2,(H,31,34)(H,32,35)(H4,28,29,30)/t23-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KUWBXRGRMQZCSS-HSZRJFAPSA-N
| C=27 | H=31 | N=5 | O=3
| smiles = C1=CC=C(C=C1)C(C2=CC=CC=C2)C(=O)N[C@H](CCCN=C(N)N)C(=O)NCC3=CC=C(C=C3)O
| synonyms = BIBP-3226
}}
BIBP-3226 is a drug used in scientific research which acts as a potent and selective antagonist for both the Neuropeptide Y receptor Y1{{cite journal | vauthors = Rudolf K, Eberlein W, Engel W, Wieland HA, Willim KD, Entzeroth M, Wienen W, Beck-Sickinger AG, Doods HN | title = The first highly potent and selective non-peptide neuropeptide Y Y1 receptor antagonist: BIBP3226 | journal = European Journal of Pharmacology | volume = 271 | issue = 2–3 | pages = R11–3 |date=December 1994 | pmid = 7705422 | doi = 10.1016/0014-2999(94)90822-2}} and also the neuropeptide FF receptor.{{cite journal | vauthors = Fang Q, Guo J, He F, Peng YL, Chang M, Wang R | title = In vivo inhibition of neuropeptide FF agonism by BIBP3226, an NPY Y1 receptor antagonist | journal = Peptides | volume = 27 | issue = 9 | pages = 2207–13 |date=September 2006 | pmid = 16762456 | doi = 10.1016/j.peptides.2006.04.002 | s2cid = 34414256 }} It was the first non-peptide antagonist developed for the Y1 receptor and has been widely used to help determine its functions in the body. Activation of Y1 is thought to be involved in functions such as regulation of appetite{{cite journal | vauthors = Kask A, Rägo L, Harro J | title = Evidence for involvement of neuropeptide Y receptors in the regulation of food intake: studies with Y1-selective antagonist BIBP3226 | journal = British Journal of Pharmacology | volume = 124 | issue = 7 | pages = 1507–15 |date=August 1998 | pmid = 9723965 | pmc = 1565528 | doi = 10.1038/sj.bjp.0701969 }} and anxiety,{{cite journal | vauthors = Kask A, Harro J, von Hörsten S, Redrobe JP, Dumont Y, Quirion R | title = The neurocircuitry and receptor subtypes mediating anxiolytic-like effects of neuropeptide Y | journal = Neuroscience and Biobehavioral Reviews | volume = 26 | issue = 3 | pages = 259–83 |date=May 2002 | pmid = 12034130 | doi = 10.1016/S0149-7634(01)00066-5| s2cid = 34688422 }} and BIBP-3226 has anxiogenic{{cite journal | vauthors = Kask A, Rägo L, Harro J | title = Anxiogenic-like effect of the NPY Y1 receptor antagonist BIBP3226 administered into the dorsal periaqueductal gray matter in rats | journal = Regulatory Peptides | volume = 75-76 | pages = 255–62 |date=September 1998 | pmid = 9802417 | doi = 10.1016/S0167-0115(98)00076-7| s2cid = 19193956 }} and anorectic effects, as well as blocking the Y1-mediated corticotropin releasing hormone release.{{cite journal | vauthors = Dimitrov EL, DeJoseph MR, Brownfield MS, Urban JH | title = Involvement of neuropeptide Y Y1 receptors in the regulation of neuroendocrine corticotropin-releasing hormone neuronal activity | journal = Endocrinology | volume = 148 | issue = 8 | pages = 3666–73 |date=August 2007 | pmid = 17463058 | doi = 10.1210/en.2006-1730 | doi-access = free }} It has also been used as a lead compound to develop a number of newer more potent Y1 antagonists.{{cite journal | vauthors = Aiglstorfer I, Hendrich I, Moser C, Bernhardt G, Dove S, Buschauer A | title = Structure-activity relationships of neuropeptide Y Y1 receptor antagonists related to BIBP 3226 | journal = Bioorganic & Medicinal Chemistry Letters | volume = 10 | issue = 14 | pages = 1597–600 |date=July 2000 | pmid = 10915060 | doi = 10.1016/S0960-894X(00)00292-4}}{{cite journal | vauthors = Weiss S, Keller M, Bernhardt G, Buschauer A, König B | title = Modular synthesis of non-peptidic bivalent NPY Y1 receptor antagonists | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 22 | pages = 9858–66 |date=November 2008 | pmid = 18851917 | doi = 10.1016/j.bmc.2008.09.033 }}