Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H22O2 |
| Molecular Weight | 186.2912 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCC[C@@H](CCC)C(O)=O
InChI
InChIKey=YCYMCMYLORLIJX-SNVBAGLBSA-N
InChI=1S/C11H22O2/c1-3-5-6-7-9-10(8-4-2)11(12)13/h10H,3-9H2,1-2H3,(H,12,13)/t10-/m1/s1
| Molecular Formula | C11H22O2 |
| Molecular Weight | 186.2912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16303147 | https://clinicaltrials.gov/ct2/show/NCT00229177 | https://clinicaltrials.gov/ct2/show/NCT00403104 | https://clinicaltrials.gov/ct2/show/NCT00212693 | https://www.ncbi.nlm.nih.gov/pubmed/28280459 | https://www.ncbi.nlm.nih.gov/pubmed/1355269
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16303147 | https://clinicaltrials.gov/ct2/show/NCT00229177 | https://clinicaltrials.gov/ct2/show/NCT00403104 | https://clinicaltrials.gov/ct2/show/NCT00212693 | https://www.ncbi.nlm.nih.gov/pubmed/28280459 | https://www.ncbi.nlm.nih.gov/pubmed/1355269
ARUNDIC ACID (ONO-2506) is an enantiomeric, three carbon atom homolog of valproic acid under development by ONO Pharmaceutical for the potential treatment of stroke, as well as Amyotrophic Lateral Sclerosis and Parkinson's disease. The injectable formulation (Proglia) is finished phase III trials for acute-phase cerebral infarction, and the oral formulation (Cereact) is finished phase II trials in the UK for Alzheimer's disease (AD) and Parkinson's disease (PD). ARUNDIC ACID restores normal astrocyte functions after brain damage by preventing reactive astrocytosis, by activating astrocytic GABAA receptors and suppressing GABA transferase. ARUNDIC ACID inhibits S-100β synthesis in activated cultured astrocytes. This agent has additional antiglutamate and antiinflammatory COX-2 inhibitor properties
CNS Activity
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
17.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
2 mg/kg/h single, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
34.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
4 mg/kg/h single, intravenous dose: 4 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
44.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
6 mg/kg/h single, intravenous dose: 6 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
66 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
8 mg/kg/h single, intravenous dose: 8 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
44.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
10 mg/kg/h single, intravenous dose: 10 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
70 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
12 mg/kg/h single, intravenous dose: 12 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
19 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
2 mg/kg/h single, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
38.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
4 mg/kg/h single, intravenous dose: 4 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
50.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
6 mg/kg/h single, intravenous dose: 6 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
57.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
8 mg/kg/h single, intravenous dose: 8 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
80.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
10 mg/kg/h single, intravenous dose: 10 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
47.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
2 mg/kg/h single, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
106.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
4 mg/kg/h single, intravenous dose: 4 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
143.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
6 mg/kg/h single, intravenous dose: 6 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
178.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
8 mg/kg/h single, intravenous dose: 8 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
210.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
10 mg/kg/h single, intravenous dose: 10 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
225 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
12 mg/kg/h single, intravenous dose: 12 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
54.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
2 mg/kg/h single, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
100 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
4 mg/kg/h single, intravenous dose: 4 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
152 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
6 mg/kg/h single, intravenous dose: 6 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
157.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
8 mg/kg/h single, intravenous dose: 8 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
223.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
10 mg/kg/h single, intravenous dose: 10 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
2 mg/kg/h single, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
4 mg/kg/h single, intravenous dose: 4 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
6 mg/kg/h single, intravenous dose: 6 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
8 mg/kg/h single, intravenous dose: 8 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
10 mg/kg/h single, intravenous dose: 10 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
12 mg/kg/h single, intravenous dose: 12 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
2 mg/kg/h single, intravenous dose: 2 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
4 mg/kg/h single, intravenous dose: 4 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
6 mg/kg/h single, intravenous dose: 6 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
8 mg/kg/h single, intravenous dose: 8 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
10 mg/kg/h single, intravenous dose: 10 mg/kg/h route of administration: Intravenous experiment type: SINGLE co-administered: |
ARUNDIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17389553/ |
ARUNDIC ACID plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Headache, Urinary tract infection... Other AEs: Headache Sources: Urinary tract infection Constipation Pyrexia Bradycardia |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Bradycardia | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Constipation | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Headache | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Pyrexia | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Urinary tract infection | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| PSAPP mice exhibit regionally selective reductions in gliosis and plaque deposition in response to S100B ablation. | 2010-11-16 |
|
| A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full. | 2010-04-22 |
|
| Targeting S100B in Cerebral Ischemia and in Alzheimer's Disease. | 2010 |
|
| S100B Protein, A Damage-Associated Molecular Pattern Protein in the Brain and Heart, and Beyond. | 2010 |
|
| Effects of S100B on Serotonergic Plasticity and Neuroinflammation in the Hippocampus in Down Syndrome and Alzheimer's Disease: Studies in an S100B Overexpressing Mouse Model. | 2010 |
|
| S100b counteracts neurodegeneration of rat cholinergic neurons in brain slices after oxygen-glucose deprivation. | 2010 |
|
| Inflammatory mechanisms in ischemic stroke: therapeutic approaches. | 2009-11-17 |
|
| Immunohistochemical analysis of brain lesions using S100B and glial fibrillary acidic protein antibodies in arundic acid- (ONO-2506) treated stroke-prone spontaneously hypertensive rats. | 2009-10 |
|
| Delayed treatment with arundic acid reduces the MPTP-induced neurotoxicity in mice. | 2008-05 |
|
| Acute astrocyte activation in brain detected by MRI: new insights into T(1) hypointensity. | 2008-03 |
|
| Pharmacokinetics of arundic acid, an astrocyte modulating agent, in acute ischemic stroke. | 2007-04 |
|
| Expression of S100 protein and protective effect of arundic acid on the rat brain in chronic cerebral hypoperfusion. | 2007-03-02 |
|
| Safety and tolerability of arundic acid in acute ischemic stroke. | 2006-12-21 |
|
| Effect of arundic acid on serum S-100beta in ischemic stroke. | 2006-12-21 |
|
| Arundic Acid ameliorates cerebral amyloidosis and gliosis in Alzheimer transgenic mice. | 2006-08 |
|
| Neuroprotective effect of arundic acid, an astrocyte-modulating agent, in mouse brain against MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) neurotoxicity. | 2006-03 |
|
| Could treatment with arundic acid (ONO-2506) increase vulnerability for depression? | 2006 |
|
| Modulation of astrocytic activation by arundic acid (ONO-2506) mitigates detrimental effects of the apolipoprotein E4 isoform after permanent focal ischemia in apolipoprotein E knock-in mice. | 2005-06 |
|
| Arundic acid (ONO-2506) ameliorates delayed ischemic brain damage by preventing astrocytic overproduction of S100B. | 2005-04 |
|
| Arundic acid, an astrocyte-modulating agent, protects dopaminergic neurons against MPTP neurotoxicity in mice. | 2004-12-24 |
|
| Gateways to clinical trials. | 2004-04 |
|
| ONO-2506. Ono. | 2003-07 |
Patents
Sample Use Guides
Stroke: Once daily one-hour intravenous infusion at 8 or 12/mg/kg/hr for 7 days
Amyotrophic Lateral Sclerosis: PO 1200 mg QD / 18 months
Route of Administration:
Other
E13.5 embryos were dissected in filter sterilized Krebs (containing the following in mM: 120.9 NaCl, 5.9 KCl, 1.2 MgCl2, 1.2 NaH2PO4, 14.4 NaHCO3, 2.5 CaCl2, and 11.5 glucose). The entire embryonic gut, including the stomach, small intestine and colon, was removed and pinned in small Sylgard dishes using 50 mm diameter tungsten wire, as described previously (Shyer et al., 2013). Gut explants were cultured in 2 ml of DMEM/F12 with 1% penicillin/streptomycin. Arundic acid (ONO-2506, Tocris Bioscience, catalog #4530) was dissolved in DMSO and added to the culture media. S100B (Sigma, cat #A6677) was dissolved in Krebs or Dulbecco’s phosphate buffered saline (DPBS) and also added to the culture media, either alone, or in combination with arundic acid. Appropriate vehicle control cultures were also performed. All preparations were incubated for 48 h at 37_C, 5% CO2 with media refreshed at 24 h.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:19:29 GMT 2025
by
admin
on
Mon Mar 31 18:19:29 GMT 2025
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| Record UNII |
F2628ZD0FO
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1509
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SUB25865
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C80993
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