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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
Structure of HYDRASTINE

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

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
208 ng/mL
1.13 mg/kg single, oral
HYDRASTINE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
495 ng × h/mL
1.13 mg/kg single, oral
HYDRASTINE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.8 h
1.13 mg/kg single, oral
HYDRASTINE serum
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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).