ULODESINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H16N4O3
Molecular Weight	264.2804
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1CN(CC2=CNC3=C2N=CNC3=O)C[C@@H]1O

InChI

InChIKey=AFNHHLILYQEHKK-BDAKNGLRSA-N

InChI=1S/C12H16N4O3/c17-5-8-3-16(4-9(8)18)2-7-1-13-11-10(7)14-6-15-12(11)19/h1,6,8-9,13,17-18H,2-5H2,(H,14,15,19)/t8-,9+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C12H16N4O3
Molecular Weight	264.2804
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/26073200 | https://adisinsight.springer.com/drugs/800020705

Ulodesine (BCX4208) is a new, orally active, highly potent inhibitor of purine nucleoside phosphorylase (PNP) for the treatment of hyperuricemia and gout. Inhibition of PNP reduces the substrates available for XO to form uric acid. The drug is currently under development for the management of hyperuricemia in chronic gout. Two Phase II clinical trials have shown promising results regarding urate-lowering effect in both as monotherapy and in combination with allopurinol. Ulodesine shows no interaction with CYP450 isoforms and has no hepatic metabolism; therefore, no drug interactions were expected. Following the successful outcome of the Phase IIb clinical trial, Phase III development of ulodesine is planned. One concern regarding the use of ulodesine is its impact on T cells. Lack of PNP is associated with immunodeficiency and autoimmune disorders.

Originator

Approval Year

PubMed

Title	Date	PubMed
Investigational drugs for hyperuricemia.	2015	26073200
New medications in development for the treatment of hyperuricemia of gout.	2015 Mar	25603039
Expert opinion on emerging urate-lowering therapies.	2018 Sep	30244605

Patents

Sample Use Guides

In Vivo Use Guide

In the 12-week randomized controlled trial, in 82 gout patients, the response rates to 5, 10, 20 and 40 mg ulodesine (BCX4208) compared with allopurinol 300 mg were 45, 33, 39 and 49%, respectively

Route of Administration: Oral

In Vitro Use Guide

Ulodesine is a novel and potent inhibitor of purine nucleoside phosphorylase (PNP) with an IC50 of 0.5 nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:26:53 GMT 2023` Edited by `admin` on `Fri Dec 15 16:26:53 GMT 2023`
Record UNII	JNG8L9460Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ULODESINE

Official Name

English

DADME-IMMUCILLIN H

Common Name

English

R-3421

Code

English

BCX-4208

Code

English

ulodesine [INN]

Common Name

English

BCX4208

Code

English

7-(((3R,4R)-3-HYDROXY-4-(HYDROXYMETHYL)PYRROLIDIN-1-YL)METHYL(-1,5-DIHYDRO-4H-PYRROLO(3,2-D)PYRIMIDIN-4-ONE

Common Name

English

Ulodesine [WHO-DD]

Common Name

English

7-(((3R,4R)-3-HYDROXY-4-(HYDROXYMETHYL)PYRROLIDIN-1-YL)METHYL)-3,5-DIHYDRO-4H-PYRROLO(3,2-D)PYRIMIDIN-4-ONE

Systematic Name

English

4H-PYRROLO(3,2-D)PYRIMIDIN-4-ONE, 1,5-DIHYDRO-7-(((3R,4R)-3-HYDROXY-4-(HYDROXYMETHYL)-1-PYRROLIDINYL)METHYL)-

Systematic Name

English

ULODESINE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2151