Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H14O3 |
Molecular Weight | 230.2592 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=O)O[C@H](C1)\C=C\C2=CC=CC=C2
InChI
InChIKey=XEAQIWGXBXCYFX-GUOLPTJISA-N
InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1
Molecular Formula | C14H14O3 |
Molecular Weight | 230.2592 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12076477Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27332705 | https://www.ncbi.nlm.nih.gov/pubmed/26918116 | https://www.ncbi.nlm.nih.gov/pubmed/18334601 | https://www.ncbi.nlm.nih.gov/pubmed/12357387
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12076477
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27332705 | https://www.ncbi.nlm.nih.gov/pubmed/26918116 | https://www.ncbi.nlm.nih.gov/pubmed/18334601 | https://www.ncbi.nlm.nih.gov/pubmed/12357387
Kavain is the main kavalactone found mostly in the roots of the kava plant. Kavain interacts with voltage-dependent Na+ and Ca2+ channels, GABAA ion channels. Kavain is found to be involved in TNF-alpha expression in human and mouse cells via regulation transcriptional factors. Kavain exhibits neuroprotective effects in models of Alzheimer's and Parkinson's diseases, and produces anxyolitic effect.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27332705 |
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Target ID: CHEMBL1075094 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18334601 |
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Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12357387 |
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Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9690349 |
88.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The efficacy of Cavain in patients suffering from anxiety. | 1989 Nov |
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Influence of genuine kavapyrone enantiomers on the GABA-A binding site. | 1998 Aug |
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Neuroprotective effects of (+/-)-kavain in the MPTP mouse model of Parkinson's disease. | 2001 Apr |
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Kava extract for treating anxiety. | 2002 |
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Kavalactones protect neural cells against amyloid beta peptide-induced neurotoxicity via extracellular signal-regulated kinase 1/2-dependent nuclear factor erythroid 2-related factor 2 activation. | 2008 Jun |
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Kavain, the Major Constituent of the Anxiolytic Kava Extract, Potentiates GABAA Receptors: Functional Characteristics and Molecular Mechanism. | 2016 |
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Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF. | 2016 Jan 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2575765
The therapeutic efficacy of Cavain should be proved in the treatment of patients suffering from abnormal anxiety, psychosomatic complaints and psychoreactive disorder. Thus two randomized groups of patients (26 each) were treated in double-blind technique with either 2 x 200 mg daily Cavain or placebo for a period of 28 days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8960869
How the excitability of neurons is affected was investigated by determining the interaction of (+/-)-kavain with epitopes (site 1, site 2) of voltage-dependent Na+ channels and the action of (+/-)-kavain on 4-aminopyridine-stimulated synaptosomes as model of repetitive firing neurons. [3H]Saxitoxin and [3H]batrachotoxin were used for radioligand-binding assays performed with synaptosomal membranes. It was shown that (+/-)-Kavain failed to compete with [3H]saxitoxin up to 400 mumol/l but dose-dependently suppressed binding of [3H]batrachotoxin with an IC50 value of 88 mumol/l (Ki = 72 mumol/l) although displacement of [3H]batrachotoxin was restricted to 33% of control at 400 mumol/l (+/-)-kavain.
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 02:49:11 UTC 2023
by
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Sat Dec 16 02:49:11 UTC 2023
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Record UNII |
W1ES06373M
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Record Status |
Validated (UNII)
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Record Version |
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2592 (Number of products:13)
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KAVAIN
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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ACTIVE MOIETY |