BIIE-0246

Details

Stereochemistry	EPIMERIC
Molecular Formula	C49H57N11O6
Molecular Weight	896.047
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)NCCC[C@H](NC(=O)CC5(CC(=O)N1CCN(CC1)C2C3=CC=CC=C3NC(=O)C4=CC=CC=C24)CCCC5)C(=O)NCCN6C(=O)N(N(C6=O)C7=CC=CC=C7)C8=CC=CC=C8

InChI

InChIKey=RSJAXPUYVJKAAA-JPGJPTAESA-N

InChI=1S/C49H57N11O6/c50-46(51)53-25-13-22-40(45(64)52-26-27-58-47(65)59(34-14-3-1-4-15-34)60(48(58)66)35-16-5-2-6-17-35)54-41(61)32-49(23-11-12-24-49)33-42(62)56-28-30-57(31-29-56)43-36-18-7-8-19-37(36)44(63)55-39-21-10-9-20-38(39)43/h1-10,14-21,40,43H,11-13,22-33H2,(H,52,64)(H,54,61)(H,55,63)(H4,50,51,53)/t40-,43?/m0/s1

HIDE SMILES / InChI

Molecular Formula	C49H57N11O6
Molecular Weight	896.047
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	1 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11937100 | https://www.ncbi.nlm.nih.gov/pubmed/10611450 | https://www.ncbi.nlm.nih.gov/pubmed/17996892 | https://www.ncbi.nlm.nih.gov/pubmed/12377370

BIIE-0246 is a highly potent, high affinity antagonist selective for the Y2 receptor subtype. BIIE-0246 is a drug used in scientific research, it was one of the first non-peptide Y2-selective antagonists developed, and remains among the most widely used tools for studying this receptor. It has been used to demonstrate a role for the Y2 subtype as a presynaptic autoreceptor limiting further neuropeptide Y release, as well as modulating dopamine and acetylcholine release. Blockade of central neuropeptide Y (NPY) Y2 receptors by BIIE-0246 has being shown to reduce ethanol self-administration in rats.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuropeptide Y receptor type 2 4 Target ID: CHEMBL4018 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10725255 \| https://www.ncbi.nlm.nih.gov/pubmed/10611450	Antagonist 2778		3.3 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alcoholism 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12377370	Primary		Preclinical	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16959374	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
BIIE0246: a selective and high affinity neuropeptide Y Y(2) receptor antagonist.	1999 Nov 19	10611450
The peptide YY-preferring receptor mediating inhibition of small intestinal secretion is a peripheral Y(2) receptor: pharmacological evidence and molecular cloning.	2001 Jul	11408607
Spontaneous release of neuropeptide Y tonically inhibits recurrent mossy fiber synaptic transmission in epileptic brain.	2005 Feb 16	15716408
Sigma 1 receptor-mediated increase in hippocampal extracellular dopamine contributes to the mechanism of the anticonvulsant action of neuropeptide Y.	2007 Dec	18005069
Anorexia induction by the trichothecene deoxynivalenol (vomitoxin) is mediated by the release of the gut satiety hormone peptide YY.	2012 Dec	22903826

Patents

Sample Use Guides

In Vivo Use Guide

Mice: BIIE-0246 was injected intraperitoneally into adult mice at 10 mg/kg.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Adjacent coronal rat brain sections were incubated with [125I]PYY3 ± 36 in the presence of increasing concentration (0.1 nM ± 10 uM) of BIIE-0246 and demonstrated that specifc [125I]PYY3 ± 36 binding was fully competed by BIIE-0246 in most brain structures. Receptor binding assays in HEK 293 cells transfected with the rat Y2 receptor cDNA demonstrated that BIIE-0246 competed with high anity (IC50=15+3 nM) against specific [125I]PYY3 ± 36 binding sites. In contrast, BIIE-0246, at concentrations up to 10 uM, failed to compete for signifcant amounts of specifc [125I]GR231118, [125I]hPP and [125I][Leu31,Pro34]PYY binding sites in HEK 293 cells transfected with the rat Y1, Y4 or Y5 receptor cDNA, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:27:33 GMT 2023` Edited by `admin` on `Sat Dec 16 09:27:33 GMT 2023`
Record UNII	N3Z657H81X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIIE-0246

Common Name

English

AR-H-053591

Code

English

CYCLOPENTANEACETAMIDE, N-((1S)-4-((AMINOIMINOMETHYL)AMINO)-1-(((2-(3,5-DIOXO-1,2-DIPHENYL-1,2,4-TRIAZOLIDIN-4-YL)ETHYL)AMINO)CARBONYL)BUTYL)-1-(2-(4-(6,11-DIHYDRO-6-OXO-5H-DIBENZ(B,E)AZEPIN-11-YL)-1-PIPERAZINYL)-2-OXOETHYL)-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

BIIE-0246