Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H21NO6 |
Molecular Weight | 383.3945 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]3([H])N(C)CCC4=C3C=C5OCOC5=C4
InChI
InChIKey=JZUTXVTYJDCMDU-MOPGFXCFSA-N
InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1
Molecular Formula | C21H21NO6 |
Molecular Weight | 383.3945 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25609220Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26821251 | https://www.ncbi.nlm.nih.gov/pubmed/25609220 | https://www.ncbi.nlm.nih.gov/pubmed/2163278
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25609220
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26821251 | https://www.ncbi.nlm.nih.gov/pubmed/25609220 | https://www.ncbi.nlm.nih.gov/pubmed/2163278
Hydrastine is an alkaloid, one of the chief components of goldenseal (Hydrastis canadensis) which was discovered in 1851 by Alfred P. Durand. Goldenseal is unique from other hydrastine containing plants in that (-)-β- hydrastine is the only hydrastine isomer present, while the (+)-enantiomer is found in other hydrastine-containing plants. . While a number of therapeutic activities have been attributed to berberine, the pharmacological effects of hydrastine are less studied and its safety profile is poorly understood and to frame the relevant pharmacological effects of hydrastine within the specific stereochemistry found in goldenseal. Hydrastine has been shown to have several specific biological activities including, inhibition of tyrosine hydroxylase in PC-12 cells, a relaxant effect on guinea pig isolated trachea, and inhibition of several cytochrome P450 (CYP) enzymes. Toxicological studies performed on goldenseal powder in mice and rats indicate that at commonly used doses goldenseal supplements are non-toxic, thus its constituents are likely to be safe for human use when taken at reasonable doses. Despite goldenseal’s widespread usage, the pharmacokinetics of hydrastine in humans has not been adequately described. While it is difficult to determine the proper dosage range for any herbal product, a recent extensive survey of the literature suggests a daily dose of Hydrastis in the range of 0.9 to 3 g per day. Hydrastine has been reported to elicit abortifacient effects and induce preterm labor in pregnant women when taken orally.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2163278 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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208 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25609220 |
1.13 mg/kg single, oral dose: 1.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
HYDRASTINE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
495 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25609220 |
1.13 mg/kg single, oral dose: 1.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
HYDRASTINE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25609220 |
1.13 mg/kg single, oral dose: 1.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
HYDRASTINE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
Title | Date | PubMed |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2. | 1998 Oct |
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Individual and combined effect of (+/-)-alpha-hydrastine and (+/-)-beta-hydrastine on spore germination of some fungi. | 2003 |
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Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers. | 2003 Dec 3 |
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Method validation for determination of alkaloid content in goldenseal root powder. | 2003 May-Jun |
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Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components. | 2003 Nov |
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[Extraction and HPLC analysis of alkaloids in goldenseal]. | 2004 Mar |
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Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine. | 2006 Jun |
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An in vitro evaluation of cytochrome P450 inhibition and P-glycoprotein interaction with goldenseal, Ginkgo biloba, grape seed, milk thistle, and ginseng extracts and their constituents. | 2007 Jul |
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Toxicology and carcinogenesis studies of goldenseal root powder (Hydrastis Canadensis) in F344/N rats and B6C3F1 mice (feed studies). | 2010 Aug |
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Problems, artifacts and solutions in the INADEQUATE NMR experiment. | 2010 Aug |
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Seasonal variation of biomass and bioactive alkaloid content of goldenseal, Hydrastis canadensis. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25609220
The disposition and metabolism of hydrastine was investigated in 11 healthy subjects following an oral dose of 2.7 g of goldenseal supplement containing 78 mg of hydrastine.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26821251
A549 cells were incubated with the indicated concentrations of (-)-β-hydrastine for 24 h. The cells were then collected, rinsed with PBS, and suspended in staining buffer (10 μg/ml propidium iodide, 0.5% Tween-20, 0.1% RNase in PBS). The cells were analyzed using a FACS Vantage flow cytometer with Cell Quest acquisition and analysis software program (Becton-Dickinson and Co., San Jose, CA, USA).
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:08:43 GMT 2023
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on
Fri Dec 15 15:08:43 GMT 2023
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Record UNII |
8890V3217X
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
1119 (Number of products:5)
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NCI_THESAURUS |
C221
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C76031
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Hydrastine
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118-08-1
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8890V3217X
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DTXSID9025409
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197835
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1313210
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757430
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CHEMBL1256919
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204-233-0
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C013024
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m6076
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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ACTIVE MOIETY |