Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H21NO6.ClH |
Molecular Weight | 419.855 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]3([H])N(C)CCC4=C3C=C5OCOC5=C4
InChI
InChIKey=URBFHJWLYXILMP-VOMIJIAVSA-N
InChI=1S/C21H21NO6.ClH/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;1H/t18-,19+;/m1./s1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2163278 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
---|---|---|
Screening for new compounds with antiherpes activity. | 1984 Oct |
|
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
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 |
|
Differential modulation of respiratory neuronal discharge patterns by GABA(A) receptor and apamin-sensitive K(+) channel antagonism. | 2001 Nov |
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Pharmacological properties of nicotinic acetylcholine receptors in isolated Locusta migratoria neurones. | 2002 Feb 15 |
|
A validated high performance liquid chromatographic method for the analysis of Goldenseal. | 2002 Mar |
|
Individual and combined effect of (+/-)-alpha-hydrastine and (+/-)-beta-hydrastine on spore germination of some fungi. | 2003 |
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Microbial transformation of the phthalideisoquinoline alkaloid, (-)-beta-hydrastine. | 2003 Aug |
|
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers. | 2003 Dec 3 |
|
Enantio-selective inhibition of (1R,9S)- and (1S,9R)-beta-hydrastines on dopamine biosynthesis in PC12 cells. | 2004 Dec |
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Effects of (1R,9S)-beta-hydrastine on l-DOPA-induced cytotoxicity in PC12 cells. | 2004 Mar 19 |
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A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis. | 2004 Nov |
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1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae). | 2004 Oct |
|
Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts. | 2005 Jun |
|
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine. | 2006 Jun |
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Effects of (1R,9S)-beta-hydrastine on intracellular calcium concentration in PC12 cells. | 2007 Aug |
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Effects of herbal products and their constituents on human cytochrome P450(2E1) activity. | 2007 Dec |
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Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.) 3: effect on human lens and retinal pigment epithelial cells. | 2007 Jul-Aug |
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Determination of hydrastine and berberine in goldenseal raw materials, extracts, and dietary supplements by high-performance liquid chromatography with UV: collaborative study. | 2008 Jul-Aug |
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Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species. | 2009 Aug 24 |
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Expanding the repertoire of small molecule transcriptional activation domains. | 2009 Feb 1 |
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Validation of a liquid chromatography-tandem mass spectrometric assay for the quantitative determination of hydrastine and berberine in human serum. | 2009 May 1 |
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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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BIAdb: a curated database of benzylisoquinoline alkaloids. | 2010 Mar 5 |
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Seasonal variation of biomass and bioactive alkaloid content of goldenseal, Hydrastis canadensis. | 2010 Oct |
|
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
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
by
admin
on
Edited
Fri Dec 15 15:01:13 UTC 2023
by
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on
Fri Dec 15 15:01:13 UTC 2023
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Record UNII |
562PDC2I9K
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Record Status |
Validated (UNII)
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Record Version |
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-
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C221
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m6076
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PRIMARY | Merck Index |
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |