BMS-470539

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H41N5O4
Molecular Weight	559.699
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC(=O)C1(CCN(CC1)C(=O)[C@@H](CC2=CC=C(OC)C=C2)NC(=O)[C@@H](N)CC3=CN=CN3C)C4=CC=CC=C4

InChI

InChIKey=GULVVTHHUIIMRL-WUFINQPMSA-N

InChI=1S/C32H41N5O4/c1-4-8-29(38)32(24-9-6-5-7-10-24)15-17-37(18-16-32)31(40)28(19-23-11-13-26(41-3)14-12-23)35-30(39)27(33)20-25-21-34-22-36(25)2/h5-7,9-14,21-22,27-28H,4,8,15-20,33H2,1-3H3,(H,35,39)/t27-,28+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C32H41N5O4
Molecular Weight	559.699
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22547573 | https://www.ncbi.nlm.nih.gov/pubmed/16888084
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12646021

BMS-470539 2 HCL (BMS-470539) is a potent, specific MC1R ligand. The affinity of this molecule, as determined by [125I]NDP-MSH competition binding experiments, was in the nanomolar range (IC50 120 nM). BMS-470539 is a potent, full agonist of recombinant human MC-1R, stably expressed in CHO cells, with an EC50 of 16.8 nM and an intrinsic activity of 88% in a cAMP accumulation assay. BMS-470539 exhibits anti-inflammatory properties following ischemia-reperfusion in the vasculature. BMS-470539 inhibits leukocyte trafficking. In mice, BMS-470539 inhibits lipopolysaccharide (LPS)-induced systemic tumour necrosis factor (TNF) release and LPS-induced leucocyte migration into the lung.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Melanocortin receptor 1 4 Target ID: CHEMBL3795 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16888084 \| https://www.ncbi.nlm.nih.gov/pubmed/22547573	Agonist 2678		16.8 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammatory diseases 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16888084 https://www.ncbi.nlm.nih.gov/pubmed/12646021 https://www.ncbi.nlm.nih.gov/pubmed/16888084 https://www.ncbi.nlm.nih.gov/pubmed/20331604	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A selective small molecule agonist of the melanocortin-1 receptor inhibits lipopolysaccharide-induced cytokine accumulation and leukocyte infiltration in mice.	2006 Oct	16888084
Selected melanocortin 1 receptor single-nucleotide polymorphisms differentially alter multiple signaling pathways.	2012 Aug	22547573

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Male BALB/c mice were dosed with BMS- 470539, as an i.v. bolus or s.c. injection at 33 umol/kg (18.47 mg/kg) in a vehicle consisting of a 50% poly(ethylene glycol)/50% water mixture (100 ul/mouse).

Route of Administration: Other

In Vitro Use Guide

BMS-470539 (10(-7) - 10(-5) M) inhibits TNFa-induced NF-kappaB activity in A549 cells expressing wild-type or variant MC1Rs.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:00:37 GMT 2023` Edited by `admin` on `Sat Dec 16 17:00:37 GMT 2023`
Record UNII	RSN3ADT27Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BMS-470539

Code

English

1H-Imidazole-5-propanamide, α-amino-N-[(1R)-1-[(4-methoxyphenyl)methyl]-2-oxo-2-[4-(1-oxobutyl)-4-phenyl-1-piperidinyl]ethyl]-1-methyl-, (αS)-

Systematic Name

English

1-[1-(3-Methyl-L-histidyl-O-methyl-D-tyrosyl)-4-phenyl-4-piperidinyl]-1-butanone

Systematic Name

English

1-Butanone, 1-[1-(3-methyl-L-histidyl-O-methyl-D-tyrosyl)-4-phenyl-4-piperidinyl]-

Systematic Name

English

BMS470539

Code

English

Code System Code Type Description

WIKIPEDIA

BMS-470539