ULODESINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H16N4O3.ClH
Molecular Weight	300.741
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=CMKFYLGNPVHLJV-RJUBDTSPSA-N

InChI=1S/C12H16N4O3.ClH/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);1H/t8-,9+;/m1./s1

HIDE SMILES / InChI

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
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.

Name

Type

Language

ULODESINE HYDROCHLORIDE

Common Name

English

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

Common Name

English

BCX-4208 HCL

Code

English

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

Systematic Name

English

BCX-4208 HYDROCHLORIDE

Code

English

Code System Code Type Description

EPA CompTox

DTXSID20210563