U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ULODESINE

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Investigational drugs for hyperuricemia.
2015
New medications in development for the treatment of hyperuricemia of gout.
2015 Mar
Expert opinion on emerging urate-lowering therapies.
2018 Sep
Patents

Sample Use Guides

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
Ulodesine is a novel and potent inhibitor of purine nucleoside phosphorylase (PNP) with an IC50 of 0.5 nM.
Name Type Language
ULODESINE
INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL269864
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY
CAS
548486-59-5
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY
PUBCHEM
135449518
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY
SMS_ID
100000175611
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
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INN
9674
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY
FDA UNII
JNG8L9460Y
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY
USAN
ZZ-07
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
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DRUG BANK
DB12353
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY
NCI_THESAURUS
C152793
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID00203332
Created by admin on Fri Dec 15 16:26:53 GMT 2023 , Edited by admin on Fri Dec 15 16:26:53 GMT 2023
PRIMARY