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[1] and also the neuropeptide FF receptor.[2] 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[3] and anxiety,[4] and BIBP-3226 has anxiogenic[5] and anorectic effects, as well as blocking the Y1-mediated corticotropin releasing hormone release.[6] It has also been used as a lead compound to develop a number of newer more potent Y1 antagonists.[7][8]

BIBP-3226
Clinical data
Other namesBIBP-3226
Identifiers
IUPAC name
  • (2R)-5-(diaminomethylideneamino)-2-([2,2-diphenylacetyl]amino)-N-[(4-hydroxyphenyl)methyl]pentanamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H31N5O3
Molar mass473.577 g·mol−1
3D model (JSmol)
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
InChI
  • InChI=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 Y
  • Key:KUWBXRGRMQZCSS-HSZRJFAPSA-N Y
 NY (what is this?)  (verify)

References
  1. Rudolf K, Eberlein W, Engel W, Wieland HA, Willim KD, Entzeroth M, Wienen W, Beck-Sickinger AG, Doods HN (December 1994). "The first highly potent and selective non-peptide neuropeptide Y Y1 receptor antagonist: BIBP3226". European Journal of Pharmacology. 271 (2–3): R11–3. doi:10.1016/0014-2999(94)90822-2. PMID 7705422.
  2. Fang Q, Guo J, He F, Peng YL, Chang M, Wang R (September 2006). "In vivo inhibition of neuropeptide FF agonism by BIBP3226, an NPY Y1 receptor antagonist". Peptides. 27 (9): 2207–13. doi:10.1016/j.peptides.2006.04.002. PMID 16762456.
  3. Kask A, Rägo L, Harro J (August 1998). "Evidence for involvement of neuropeptide Y receptors in the regulation of food intake: studies with Y1-selective antagonist BIBP3226". British Journal of Pharmacology. 124 (7): 1507–15. doi:10.1038/sj.bjp.0701969. PMC 1565528. PMID 9723965.
  4. Kask A, Harro J, von Hörsten S, Redrobe JP, Dumont Y, Quirion R (May 2002). "The neurocircuitry and receptor subtypes mediating anxiolytic-like effects of neuropeptide Y". Neuroscience and Biobehavioral Reviews. 26 (3): 259–83. doi:10.1016/S0149-7634(01)00066-5. PMID 12034130.
  5. Kask A, Rägo L, Harro J (September 1998). "Anxiogenic-like effect of the NPY Y1 receptor antagonist BIBP3226 administered into the dorsal periaqueductal gray matter in rats". Regulatory Peptides. 75–76: 255–62. doi:10.1016/S0167-0115(98)00076-7. PMID 9802417.
  6. Dimitrov EL, DeJoseph MR, Brownfield MS, Urban JH (August 2007). "Involvement of neuropeptide Y Y1 receptors in the regulation of neuroendocrine corticotropin-releasing hormone neuronal activity". Endocrinology. 148 (8): 3666–73. doi:10.1210/en.2006-1730. PMID 17463058.
  7. Aiglstorfer I, Hendrich I, Moser C, Bernhardt G, Dove S, Buschauer A (July 2000). "Structure-activity relationships of neuropeptide Y Y1 receptor antagonists related to BIBP 3226". Bioorganic & Medicinal Chemistry Letters. 10 (14): 1597–600. doi:10.1016/S0960-894X(00)00292-4. PMID 10915060.
  8. Weiss S, Keller M, Bernhardt G, Buschauer A, König B (November 2008). "Modular synthesis of non-peptidic bivalent NPY Y1 receptor antagonists". Bioorganic & Medicinal Chemistry. 16 (22): 9858–66. doi:10.1016/j.bmc.2008.09.033. PMID 18851917.


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