Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H10Br2N2O3 |
Molecular Weight | 414.0484 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cncc2c1OCCN2C(=O)c3cc(c(c(c3)Br)O)Br
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
Molecular Formula | C14H10Br2N2O3 |
Molecular Weight | 414.0484 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
(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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q96S37|||Q96DT2 Gene ID: 116085.0 Gene Symbol: SLC22A12 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26907620 |
57.0 nM [Ki] |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26907620
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26907620
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
Edited
Fri Jun 25 22:42:25 UTC 2021
by
admin
on
Fri Jun 25 22:42:25 UTC 2021
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Record UNII |
0YP1ME85GH
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Record Status |
Validated (UNII)
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Record Version |
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C166441
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10723
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1198153-15-9
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44608229
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0YP1ME85GH
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
UR-1102 inhibited urate uptake by HEK293 cells transiently expressing URAT1,
SELECTIVE
Ki
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OFF-TARGET->INHIBITOR |
PAH uptake by HEK293 cells transiently expressing OAT1
WEAK INHIBITOR
Ki
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OFF-TARGET->INHIBITOR |
PAH uptake by HEK293 cells transiently expressing OAT3
WEAK INHIBITOR
Ki
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Related Record | Type | Details | ||
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ACTIVE MOIETY |