Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H11NO3 |
| Molecular Weight | 205.2099 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1CC(=NO1)C2=CC=CC=C2
InChI
InChIKey=MUFJHYRCIHHATF-UHFFFAOYSA-N
InChI=1S/C11H11NO3/c13-11(14)7-9-6-10(12-15-9)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)
| Molecular Formula | C11H11NO3 |
| Molecular Weight | 205.2099 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17148780 | https://www.ncbi.nlm.nih.gov/pubmed/17449326
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17148780 | https://www.ncbi.nlm.nih.gov/pubmed/17449326
(S,R)-3-Phenyl-4,5-dihydro-5-isoxasole acetic acid (VGX-1027, GIT-027) is an isoxazole compound that exhibits various immunomodulatory properties.
This compound reduced the secretion of IL-1beta, TNF-alpha and IL-10 from purified murine macrophages stimulated "in vitro" with lipopolysaccharide (LPS), and it also modified the signaling pathways induced in these cells by LPS entailing reduced activation of NF-kappaB and p38 MAP kinase pathways along with up-regulation of ERK pathways. The animals receiving VGX-1027 exhibited reduced production of the proinflammatory mediators tumor necrosis factor-alpha, IL-1beta, macrophage migration inhibitory factor, and inducible nitric-oxide synthase-mediated nitric oxide generation in both pancreatic islets and peripheral compartments. Inovio Pharmaceuticals is developing VGX-1027 for the treatment of inflammatory conditions such as rheumatoid arthritis, type 1 diabetes mellitus, uveitis and ulcerative colitis.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.13 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.87 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.89 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
16.58 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
14.62 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13.46 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
17.48 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.05 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.07 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.83 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
16.56 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
24.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
44.14 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.63 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.66 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
|
3.69 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.18 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
31.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
25.62 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
90.58 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
78.63 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
59.74 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
88.53 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
88.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
115.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
172.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
361.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
40.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
56.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
|
18.53 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.07 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
11.23 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.53 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg 1 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.87 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
|
7.73 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138022/ |
40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ZENUZOLAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Safety, bioavailability, and pharmacokinetics of VGX-1027-A novel oral anti-inflammatory drug in healthy human subjects. | 2016-03 |
|
| Podocyte apoptosis is prevented by blocking the Toll-like receptor pathway. | 2015-05-07 |
|
| VGX-1027 modulates genes involved in lipopolysaccharide-induced Toll-like receptor 4 activation and in a murine model of systemic lupus erythematosus. | 2014-08 |
|
| High mobility group box protein-1 promotes cerebral edema after traumatic brain injury via activation of toll-like receptor 4. | 2014-01 |
|
| Renal protective effects of toll-like receptor 4 signaling blockade in type 2 diabetic mice. | 2013-06 |
|
| Effects of the immunomodulator, VGX-1027, in endotoxin-induced uveitis in Lewis rats. | 2008-11 |
|
| In vitro inhibition of enterobacteria-reactive CD4+CD25- T cells and suppression of immunoinflammatory colitis in mice by the novel immunomodulatory agent VGX-1027. | 2008-05-31 |
|
| In vitro, ex vivo and in vivo immunopharmacological activities of the isoxazoline compound VGX-1027: modulation of cytokine synthesis and prevention of both organ-specific and systemic autoimmune diseases in murine models. | 2007-06 |
|
| A potent immunomodulatory compound, (S,R)-3-Phenyl-4,5-dihydro-5-isoxazole acetic acid, prevents spontaneous and accelerated forms of autoimmune diabetes in NOD mice and inhibits the immunoinflammatory diabetes induced by multiple low doses of streptozotocin in CBA/H mice. | 2007-03 |
Sample Use Guides
The safety, tolerability, and pharmacokinetics of single (1-800 mg) and multiple (40-400 mg) oral doses were evaluated in 2 clinical studies (NCT00627120, NCT00760396). The doses were well tolerated up to 800 mg in a single dose and 200 mg twice daily in multiple doses.
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 16:40:11 GMT 2025
by
admin
on
Tue Apr 01 16:40:11 GMT 2025
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| Record UNII |
AKT814N13R
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| Record Status |
Validated (UNII)
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| Code System | Code | Type | Description | ||
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C184883
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VGX-1027
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VGX-1027
Created by
admin on Tue Apr 01 16:40:11 GMT 2025 , Edited by admin on Tue Apr 01 16:40:11 GMT 2025
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PRIMARY | Biochem/physiol Actions: VGX-1027 is a potent nitric oxide-donating immunomodulatory compound, which markedly decreased the cumulative incidence of diabetes and insulitis in NOD mice model with spontaneous or accelerated forms of diabetes induced either by injection of cyclophosphamide or by transfer of spleen cells from acutely diabetic syngeneic donors. | ||
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DTXSID50445023
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300000036069
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12006
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AKT814N13R
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10798271
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6501-72-0
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CHEMBL1320667
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
Class: Anti-inflammatory, Isoxazole, Small molecule; Mechanism of Action: NF-kappa B inhibitor, P38 mitogen-activated protein kinase inhibitor; Highest Development Phase: Phase I for Rheumatoid arthritis, Type 1 diabetes mellitus, Preclinical for Ulcerative colitis, Uveitis; Most Recent Events: 28 May 2010 Preparation for phase II trials of VGX 1027 is still underway for type 1 Diabetes mellitus and Rheumatoid arthritis in USA, 14 May 2010 Inovio Biomedical is now called Inovio Pharmaceuticals, 01 May 2010 Preclinical trials in Ulcerative colitis in USA (PO)
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