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

Details

Stereochemistry ACHIRAL
Molecular Formula C14H10Br2N2O3
Molecular Weight 414.049
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPAMINURAD

SMILES

OC1=C(Br)C=C(C=C1Br)C(=O)N2CCOC3=CC=NC=C23

InChI

InChIKey=ZMVGQIIOXCGAFV-UHFFFAOYSA-N
InChI=1S/C14H10Br2N2O3/c15-9-5-8(6-10(16)13(9)19)14(20)18-3-4-21-12-1-2-17-7-11(12)18/h1-2,5-7,19H,3-4H2

HIDE SMILES / InChI

Molecular Formula C14H10Br2N2O3
Molecular Weight 414.049
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

(3,5-DIBROMO-4-HYDROXYPHENYL)(2,3-DIHYDRO-4H-PYRIDO[4,3-B][1,4]OXAZIN-4-YL)METHANONE (UR-1102/URC-1022) is currently under development for the management of hyperuricaemia in gout. It is a selective URAT1 inhibitor with Ki of 57 nM showing higher uricosuric effects than benzbromarone in monkeys with potentially lower mitochondrial toxicity which is supposed to be related to hepatotoxicity. There is also a probable inhibition of OAT1 and OAT3. UR-1102, which is derived from the chemical structure of benzbromarone, was designed to not only improve URAT1 selectivity and solubility but also to avoid the hepatic toxicity concern of benzbromarone, which is known to be associated with hepatic injury and to have the potential to cause fulminant hepatitis in humans. The results of two phase II trials presented at the 2017 ACR meeting suggested a high potency for reducing SU levels with a good safety profile on a short follow-up. No phase III trial has been registered so far.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
57.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Investigational drugs for hyperuricemia, an update on recent developments.
2018 May
Expert opinion on emerging urate-lowering therapies.
2018 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
UR-1102 at 3-30 mg/kg or benzbromarone at 3-100 mg/kg was administered orally once a day for 3 consecutive days to tufted capuchin monkeys
Route of Administration: Oral
In Vitro Use Guide
Although the Ki value for UR-1102 against URAT1 was comparable to that of benzbromarone (0.057 umol/l versus 0.052 umol/l), the Ki values for UR-1102 against OAT1 and OAT3 just exceeded 10 times the Ki values of benzbromarone (OAT1: 7.2 umol/l versus 0.22 umol/l; OAT3: 2.4 umol/l versus 0.11 umol/l)
Substance Class Chemical
Created
by admin
on Tue Oct 22 08:12:13 UTC 2019
Edited
by admin
on Tue Oct 22 08:12:13 UTC 2019
Record UNII
0YP1ME85GH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPAMINURAD
INN  
Official Name English
METHANONE, (3,5-DIBROMO-4-HYDROXYPHENYL)(2,3-DIHYDRO-4H-PYRIDO(4,3-B)-1,4-OXAZIN-4-YL)-
Systematic Name English
EPAMINURAD [INN]
Common Name English
(3,5-DIBROMO-4-HYDROXYPHENYL)(2,3-DIHYDRO-4H-PYRIDO(4,3-B)-1,4-OXAZIN-4-YL)METHANONE
Systematic Name English
UR-1102
Code English
Code System Code Type Description
INN
10723
Created by admin on Tue Oct 22 08:12:13 UTC 2019 , Edited by admin on Tue Oct 22 08:12:13 UTC 2019
PRIMARY
CAS
1198153-15-9
Created by admin on Tue Oct 22 08:12:13 UTC 2019 , Edited by admin on Tue Oct 22 08:12:13 UTC 2019
PRIMARY
PUBCHEM
44608229
Created by admin on Tue Oct 22 08:12:13 UTC 2019 , Edited by admin on Tue Oct 22 08:12:13 UTC 2019
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
UR-1102 inhibited urate uptake by HEK293 cells transiently expressing URAT1,
SELECTIVE
Ki
OFF-TARGET->INHIBITOR
PAH uptake by HEK293 cells transiently expressing OAT1
WEAK INHIBITOR
Ki
OFF-TARGET->INHIBITOR
PAH uptake by HEK293 cells transiently expressing OAT3
WEAK INHIBITOR
Ki
Related Record Type Details
ACTIVE MOIETY