BIBP-3226

BIBP-3226

Systematic (IUPAC) name
(2R)-5-(diaminomethylideneamino)-2-([2,2-diphenylacetyl]amino)-N-[(4-hydroxyphenyl)methyl]pentanamide
Identifiers
CAS Number	159013-54-4
PubChem	CID 5311023
IUPHAR/BPS	1485
ChemSpider	4470561
ChEMBL	CHEMBL332347
Synonyms	BIBP-3226
Chemical data
Formula	C27H31N5O3
Molar mass	473.566 g/mol
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 Key:KUWBXRGRMQZCSS-HSZRJFAPSA-N
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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]

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.