UK-432097

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C40H47N11O6
Molecular Weight	777.8713
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=C(N=C3NCC(C4=CC=CC=C4)C5=CC=CC=C5)C(=O)NCCNC(=O)NC6CCN(CC6)C7=NC=CC=C7

InChI

InChIKey=ZOTHAEBAWXWVID-HXEFRTELSA-N

InChI=1S/C40H47N11O6/c1-2-41-37(54)33-31(52)32(53)39(57-33)51-24-46-30-34(45-23-28(25-11-5-3-6-12-25)26-13-7-4-8-14-26)48-35(49-36(30)51)38(55)43-19-20-44-40(56)47-27-16-21-50(22-17-27)29-15-9-10-18-42-29/h3-15,18,24,27-28,31-33,39,52-53H,2,16-17,19-23H2,1H3,(H,41,54)(H,43,55)(H2,44,47,56)(H,45,48,49)/t31-,32+,33-,39+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22824275 | http://adisinsight.springer.com/drugs/800022635
Curator's Comment: Description was created based on several sources, including https://www.pharmacodia.com/yaodu/html/v1/chemicals/127d2e587fe09591c67b04c7c7190479.html

UK-432097 is a selective adenosine A2a agonist which was in development with Pfizer as an inhaled treatment for asthma and chronic obstructive pulmonary disease. UK-432097 had been in phase II clinical trials by Pfizer for the treatment of chronic obstructive pulmonary disease (COPD). However, this study was terminated prematurely due to futility based on results of interim analysis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A2a receptor 30 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19501510	Agonist 2678		4.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: https://clinicaltrials.gov/ct2/show/NCT00430300 http://adisinsight.springer.com/drugs/800022635	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
50 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22077102	4500 μg single, respiratory dose: 4500 μg route of administration: Respiratory experiment type: SINGLE co-administered:		UK-432097 plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22077102	unknown, unknown		UK-432097 blood	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
1.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26236482	unknown, unknown		UK-432097 plasma	Rattus norvegicus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		ABC8 1 CYP27A1 1 ABC1 1 LXRA 1

Drug as perpetrator

Target	Modality	Activity
ABC1 1	inducer 1573 Sources: https://www.academia.edu/download/50500216/69.pdf	yes
ABC8 1	inducer 1573 Sources: https://www.academia.edu/download/50500216/69.pdf	yes
CYP27A1 1	inducer 1573 Sources: https://www.academia.edu/download/50500216/69.pdf	yes
LXRA 1	inducer 1573 Sources: https://www.academia.edu/download/50500216/69.pdf	yes

Sourcing

Vendor/Aggregator	ID	URL
Axon MedChem	1193	https://www.axonmedchem.com/product/1193
MolPort	MolPort-042-665-665	https://www.molport.com/shop/molecule-link/MolPort-042-665-665
Sigma Aldrich	PZ0337	http://www.sigmaaldrich.com/catalog/search?term=PZ0337&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
eMolecules	260824358	https://orderbb.emolecules.com/search/#?query=260824358
eMolecules	36745688	https://orderbb.emolecules.com/search/#?query=36745688

PubMed

Title	Date	PubMed
Structure of an agonist-bound human A2A adenosine receptor.	2011 Apr 15	21393508

Patents

Sample Use Guides

In Vivo Use Guide

Formulated as a dry powder, supplied as capsules and administered using an atomizer device. Given as either 150mcg, 450mcg or 1350mcg BID.

Route of Administration: Intratracheal

In Vitro Use Guide

UK-432097 (1uM) potently increased beta-cell proliferation in mouse islets in vitro

Name

Type

Language

UK-432097

Common Name

English

.BETA.-D-RIBOFURANURONAMIDE, 1-DEOXY-1-(6-((2,2-DIPHENYLETHYL)AMINO)-2-(((2-((((1-(2-PYRIDINYL)-4-PIPERIDINYL)AMINO)CARBONYL)AMINO)ETHYL)AMINO)CARBONYL)-9H-PURIN-9-YL)-N-ETHYL-

Systematic Name

English

UK-432,097

Code

English

6-((2,2-DIPHENYLETHYL)AMINO)-9-(N-ETHYL-.BETA.-D-RIBOFURANOSYLURONAMIDE)-N-(2-(N'-(1-(2-PYRIDYL)-4-PIPERIDYL)UREIDO)ETHYL)-9H-PURINE-2-CARBOXAMIDE

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL1096896