BIBP3226 | CAS#159013-54-4 | NPY Y1 receptor antagonist

BIBP3226
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531551

CAS#: 159013-54-4

Description: BIBP3226 is a nonpeptide antagonist of neuropeptide Y (NPY) receptor Y1 (Ki = 1.1 nM).1 It is selective for Y1 over Y2, Y4, and Y5 receptors (Kis = >1,000 nM for all). It also binds to neuropeptide FF receptor 1 (NPFF1) and NPFF2 (Kis = 108 and 79 nM, respectively) and reverses NPFF-induced inhibition of forskolin-induced cAMP accumulation in CHO cells expressing human NPFF2 in a concentration-dependent manner. BIBP3226 inhibits NPY-induced increases in perfusion pressure in isolated rat kidney but not the NPY-induced twitch response in isolated rat vas deferens (IC50s = 26 and >10,000 nM, respectively). BIBP3226 inhibits NPY-induced increases in blood pressure in pithed rats (ED50 = 0.11 mg/kg). It also inhibits NPFF-induced hypothermia in mice when administered intracerebroventricularly (i.c.v.) at a dose of 5 nmol.

Chemical Structure

BIBP3226

CAS# 159013-54-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531551
Name: BIBP3226
CAS#: 159013-54-4
Chemical Formula: C27H31N5O3
Exact Mass: 473.24
Molecular Weight: 473.580
Elemental Analysis: C, 68.48; H, 6.60; N, 14.79; O, 10.13

Price and Availability

Size	Price	Availability
5mg	USD 450	2 Weeks
10mg	USD 750	2 Weeks
25mg	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: BIBP3226; BIBP 3226; BIBP-3226;

IUPAC/Chemical Name: (2R)-5-(diaminomethylideneamino)-2-[[2,2-di(phenyl)acetyl]amino]-N-[(4-hydroxyphenyl)methyl]pentanamide

InChi Key: KUWBXRGRMQZCSS-HSZRJFAPSA-N

InChi Code: 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

SMILES Code: O=C(NCC1=CC=C(O)C=C1)[C@H](NC(C(C2=CC=CC=C2)C3=CC=CC=C3)=O)CCC/N=C(N)\N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	BIBP3226 TFA is a neuropeptide Y Y1 (NPY Y1) and neuropeptide FF (NPFF) receptor antagonist, with Kis of 1.1, 79, and 108 nM for rNPY Y1, hNPFF2, and rNPFF, respectively.
In vitro activity:	The NPY Y1 selective antagonist BIBP3226 inhibited the vascular effects of neuropeptide Y (NPY) in vitro (IC50 =126 nM). BIBP3226 also inhibited the effects of the selective Y1 agonist [Leu31,Pro34]NPY and completely abolished the effects of avian pancreatic polypeptide that was shown to be capable of potentiating neurogenic vasoconstriction. Reference: Life Sci. 1998;62(6):525-32. https://www.sciencedirect.com/science/article/abs/pii/S002432059701148X?via%3Dihub
In vivo activity:	The antagonistic effects of BIBP3226 on several in vivo pharmacologic profiles induced by exogenous NPFF and NPVF was investigated. BIBP3226 (5 nmol) injected into the third ventricle completely antagonized the hypothermic effects of NPFF (30 nmol) and NPVF (30 nmol) after cerebral administration in mice; BIBP3226 (5 nmol, i.c.v.) prevented the anti-morphine actions of NPFF (10 nmol, i.c.v.) in the mouse tail-flick assay; in urethane-anaesthetized rats, both NPFF (200 nmol/kg, i.v.) and NPVF (200 nmol/kg, i.v.) increased the mean arterial blood pressure, which were significantly reduced by pretreatment with BIBP3226 (500 nmol/kg, i.v.). Collectively, these data suggest that BIBP3226, a mixed antagonist of NPY Y1 and NPFF receptors, shows in vivo antagonistic effects on NPFF receptors. Reference: Peptides. 2006 Sep;27(9):2207-13. https://www.sciencedirect.com/science/article/abs/pii/S0196978106001902?via%3Dihub

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	250.0	527.89

Preparing Stock Solutions

The following data is based on the product molecular weight 473.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Barrios VE, Nelson AG, Toombs CF. BIBP3226 inhibits neuropeptide Y and pancreatic polypeptide potentiated neurogenic vasoconstriction. Life Sci. 1998;62(6):525-32. doi: 10.1016/s0024-3205(97)01148-x. PMID: 9464464. 2. Fang Q, Guo J, He F, Peng YL, Chang M, Wang R. In vivo inhibition of neuropeptide FF agonism by BIBP3226, an NPY Y1 receptor antagonist. Peptides. 2006 Sep;27(9):2207-13. doi: 10.1016/j.peptides.2006.04.002. Epub 2006 Jun 9. PMID: 16762456.
In vitro protocol:	1. Barrios VE, Nelson AG, Toombs CF. BIBP3226 inhibits neuropeptide Y and pancreatic polypeptide potentiated neurogenic vasoconstriction. Life Sci. 1998;62(6):525-32. doi: 10.1016/s0024-3205(97)01148-x. PMID: 9464464.
In vivo protocol:	1. Fang Q, Guo J, He F, Peng YL, Chang M, Wang R. In vivo inhibition of neuropeptide FF agonism by BIBP3226, an NPY Y1 receptor antagonist. Peptides. 2006 Sep;27(9):2207-13. doi: 10.1016/j.peptides.2006.04.002. Epub 2006 Jun 9. PMID: 16762456.

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1: Fang Q, Guo J, He F, Peng YL, Chang M, Wang R. In vivo inhibition of neuropeptide FF agonism by BIBP3226, an NPY Y1 receptor antagonist. Peptides. 2006 Sep;27(9):2207-13. PubMed PMID: 16762456.

2: Engström M, Wurster S, Savola JM, Panula P. Functional properties of Pfr(Tic)amide and BIBP3226 at human neuropeptide FF2 receptors. Peptides. 2003 Dec;24(12):1947-54. PubMed PMID: 15127947.

3: Chen SH, Cheung RT. Intracerebroventricular injection of a neuropeptide Y-Y1 receptor agonist increases while BIBP3226, a Y1 antagonist, reduces the infarct volume following transient middle cerebral artery occlusion in rats. Neuroscience. 2003;116(1):119-26. PubMed PMID: 12535945.

4: Van Liefde, Vanderheyden PM, De Backer JP, Ebinger G, Vauquelin G. Effects of BIBP3226 and BIBP3435 on cytosolic calcium in neuropeptide Y Y1 receptor-transfected Chinese hamster ovary cells and wild type CHO-K1 cells. J Recept Signal Transduct Res. 2001 Feb;21(1):11-23. PubMed PMID: 11693170.

5: Mollereau C, Gouardères C, Dumont Y, Kotani M, Detheux M, Doods H, Parmentier M, Quirion R, Zajac JM. Agonist and antagonist activities on human NPFF(2) receptors of the NPY ligands GR231118 and BIBP3226. Br J Pharmacol. 2001 May;133(1):1-4. PubMed PMID: 11325787; PubMed Central PMCID: PMC1572765.

6: Kask A, Kivastik T, Rägo L, Harro J. Neuropeptide Y Y1 receptor antagonist BIBP3226 produces conditioned place aversion in rats. Prog Neuropsychopharmacol Biol Psychiatry. 1999 May;23(4):705-11. PubMed PMID: 10390728.

7: Vanderheyden PM, Van Liefde I, de Backer JP, Vauquelin G. [3H]-BIBP3226 and [3H]-NPY binding to intact SK-N-MC cells and CHO cells expressing the human Y1 receptor. J Recept Signal Transduct Res. 1998 Jul-Nov;18(4-6):363-85. PubMed PMID: 9879066.

8: Kask A, Rägo L, Harro J. Anxiogenic-like effect of the NPY Y1 receptor antagonist BIBP3226 administered into the dorsal periaqueductal gray matter in rats. Regul Pept. 1998 Sep 25;75-76:255-62. PubMed PMID: 9802417.

9: Vanderheyden PM, Van Liefde I, DeBacker JP, Ebinger G, Vauquelin G. Effect of BIBP3226 on inositol phosphate accumulation and cytosolic calcium level in control and NPY Y1 receptor expressing CHO-K1 cells. Regul Pept. 1998 Sep 25;75-76:191-9. PubMed PMID: 9802409.

10: Gariboldi M, Conti M, Cavaleri D, Samanin R, Vezzani A. Anticonvulsant properties of BIBP3226, a non-peptide selective antagonist at neuropeptide Y Y1 receptors. Eur J Neurosci. 1998 Feb;10(2):757-9. PubMed PMID: 9749738.

11: Kask A, Rägo L, Harro J. Evidence for involvement of neuropeptide Y receptors in the regulation of food intake: studies with Y1-selective antagonist BIBP3226. Br J Pharmacol. 1998 Aug;124(7):1507-15. PubMed PMID: 9723965; PubMed Central PMCID: PMC1565528.

12: Barrios VE, Nelson AG, Toombs CF. BIBP3226 inhibits neuropeptide Y and pancreatic polypeptide potentiated neurogenic vasoconstriction. Life Sci. 1998;62(6):525-32. PubMed PMID: 9464464.

13: Widdowson PS, Buckingham R, Williams G. Distribution of [Leu31,Pro34]NPY-sensitive, BIBP3226-insensitive [125I]PYY(3-36) binding sites in rat brain: possible relationship to Y5 NPY receptors. Brain Res. 1997 Dec 5;778(1):242-50. PubMed PMID: 9462897.

14: Kask A, Rägo L, Harro J. Alpha-helical CRF(9-41) prevents anxiogenic-like effect of NPY Y1 receptor antagonist BIBP3226 in rats. Neuroreport. 1997 Nov 10;8(16):3645-7. PubMed PMID: 9427342.

15: Vanderheyden PM, Van Liefde I, De Backer JP, Vauquelin G. Non-competitive binding of the nonpeptide antagonist BIBP3226 to rat forebrain neuropeptide Y1 receptors. Eur J Pharmacol. 1997 Jul 23;331(2-3):275-84. PubMed PMID: 9274990.

16: Kask A, Rägo L, Harro J. Anxiogenic-like effect of the neuropeptide Y Y1 receptor antagonist BIBP3226: antagonism with diazepam. Eur J Pharmacol. 1996 Dec 19;317(2-3):R3-4. PubMed PMID: 8997632.

17: Yang SN, Finnman UB, Fuxe K. The non-peptide neuropeptide Y Y1 receptor antagonist BIBP3226 blocks the [Leu31,Pro34]neuropeptide Y-induced modulation of alpha 2-adrenoceptors in the nucleus tractus solitarii of the rat. Neuroreport. 1996 Nov 4;7(15-17):2701-5. PubMed PMID: 8981451.

18: Grundemar L, Ekelund M. Effects of the neuropeptide Y (NPY)-receptor antagonist BIBP3226 on vascular NPY-receptors with different ligand requirements. Pharmacol Toxicol. 1996 Nov;79(5):266-9. PubMed PMID: 8936561.

19: Tough IR, Cox HM. Selective inhibition of neuropeptide Y Y1 receptors by BIBP3226 in rat and human epithelial preparations. Eur J Pharmacol. 1996 Aug 22;310(1):55-60. PubMed PMID: 8880067.

20: Dumont Y, St-Pierre JA, Quirion R. Comparative autoradiographic distribution of neuropeptide Y Y1 receptors visualized with the Y1 receptor agonist [125I][Leu31,Pro34]PYY and the non-peptide antagonist [3H]BIBP3226. Neuroreport. 1996 Mar 22;7(4):901-4. PubMed PMID: 8724669.

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